Productive Flourishing Podcast

What do we do when we’re feeling guilty about not being productive? Today’s episode is a discussion on the topic of productivity guilt. Charlie and Angela discuss some of the different ways productivity guilt can manifest itself, as well as provide some perspective and encouragement about whether we’re truly not being productive. These guidelines can help determine whether a change needs to be made.Key Takeaways:[2:14] - Oftentimes, when we talk about productivity, we focus on work and primarily the work we are not doing. But usually, to feel that guilt, you are doing something.[3:45] - Anything you do that helps you flourish and become the person you want to be in the world, can and should be counted as productive. Eating, exercising, being a great a parent - all of these things make you a productive person.[6:12] - Is what you’re doing actually a waste of time? This is a question you can use to help yourself gauge whether you’re really being productive. Charlie suggests evaluating a task by determining if you’re generating the results you need to be generating. If you’re not, something may need to change.[9:20] - We are hardwired to be productive. Your body can be a good indicator of when you are accomplishing things, and on the flip side, when there are changes that you may need make.[11:05] - Many people have the assumption about themselves that they are not a productive person. Everyone should have the assumption that they are productive, they are creative, and they want to get things done. When you’re doubting your productivity, whose voice and judgment are you using to determine that?[12:53] - Charlie and Angela discuss our habit of comparing ourselves to others, and the trend of being okay with some aspect of ourselves (salary, level of productivity), until you learn about someone else’s and start comparing yourself to them. The more your friends are high achievers, the more you have to watch out for this. You have to have a lot of information about someone’s general context before you can fairly evaluate yourself against them.[16:24] - When we talk about comparing ourselves to others and feeling guilt, it comes back to a conversation about priorities. If you are clear about what your priorities are, and you’re spending your time and energy on them, that’s the way it should be! The results may be different from someone else’s, but that’s because your priorities are different.[19:57] - Today’s pace of life is setting the scenario for not allowing ourselves space to be human, and we’re trying to do a lot. Setting realistic expectations for what you can commit to, achieve, and be proud of can be good motivation. Stand on small successes and build from there.[23:42] - For entrepreneurs, if you’ve been planting for a long time but you’re not yielding what you want, you may have a money model problem. You’re not alone! You may have to find another economic outlet that you can do simultaneously while growing your business.[27:35] - The conversation about productivity is not just about things counted, but about moments spent and lives nourished. Looking at it this way can give you a better lens for whether you’re being productive or not.Mentioned in This Episode:Productive FlourishingLeave a Review This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.productiveflourishing.com/subscribe

The decision to go all in can be a big one. Today’s guest, Ronen Gafni, founder of Fresh Biz and co-author of The New Entrepreneurs, joins Charlie to discuss the importance of going all in and betting on yourself. In addition to discussing some misconceptions about what it means to go all in, they also talk about some of the counter-intuitive truths about entrepreneurship, especially how it relates to how you’re charging for your value.Key Takeaways:[2:20] - There are three different types of “going all in.” Ronen relates them to poker: The first type is throwing yourself into something with no skill or idea of how it works. The second type is going all in thinking you can fool those around you that you know what you’re doing. The third way that Ronen is talking about is when you know you have a winning hand, and you’re willing to risk something to really go for it.[5:30] - Sometimes, we have trouble putting all our chips on us and our own abilities. Ronen encourages people to begin to trust themselves more and bet on themselves. It’s a little harder than going in on external systems, where we have someone else to blame when things go wrong.[8:32] - How do you determine if you have a good hand or not? When it comes to entrepreneurship, it’s not about having the best hand at the table; it’s just about having a good hand. You don’t have to be the only one who is winning - there are all kinds of different wins. The first element to a good hand is the ability to learn, and the second is to understand and know that you can handle the falls and the punches you will face.[13:03] - There are foundations for creative and entrepreneurial successes. Knowing when to stick and when to pivot, and knowing the core things that customers value can take you a long way. It is important to cover these basics so you can focus on the uniqueness and the value that you bring. At the end of the day, the only competition is about getting the attention of the customer.[16:30] - Ronen shares the story of getting to a point of going all in on a business. FreshBiz started in this way. FreshBiz is a training company based on a board game that Ronen developed - it teaches you the skills to know and understand today’s economy. The original idea was just to develop a game, but once it was developed, he had to decide if it was going to become a business, or just be a project he was a part of and be put aside. One of the concerns was his debt, and in order to make FreshBiz a business, he had to decide if he was going to sell his house to pay back the debt and invest the rest in the business.[20:40] - While this was going on with Ronen’s business, he also had a commitment to his family. His wife, who is like-minded about self-development, was open to the conversation about selling their house to alleviate some credit card debt and fulfilling the goals of FreshBiz. Coming at it from a self-development perspective made it easier to discuss, though the decision was still difficult.[26:21] - The infrastructure of the self-development process is very important. It’s always about the mindset and the story you choose to tell yourself. A big discussion for Ronen and his wife was whether they were really connected to the specific house itself, and then it became a financial decision: would they be able to sell this house and make more money in their business to buy a new home?[31:45] - Ronen’s original idea for FreshBiz was just to be the game, but it quickly became something more meaningful for other people. It grew organically as people were seeking a way to better understand themselves. For Ronen, the entire process was figuring out how the game generateed a way for people to understand themselves.[37:00] - For a lot of entrepreneurs, the thing that’s most natural and easiest for you is usually the thing that other people latch onto as being incredibly valuable. These are the things you should be charging the most for, rather than the things that are hard for you. It is a big step for many entrepreneurs to recognize their gift and charge for it.[39:52] - Right now, Ronen’s new challenge is looking at going all in globally. They are active in about 20 countries, and are looking at travelling more to grow the business around the globe. Some of the things keeping him from jumping all in are family (being away from his wife and kids), as well as the flying and travelling.[42:15] - Charlie and Ronen talk about sufficiency points - this is about finding the right level for your business and your life. For Ronen, moving to the next level is not necessarily about the business goals, but has more to do with his mission in life. He wants to personally deliver his message to different parts of the world.[45:50] - Ronen’s invitation for listeners: Go all in for something that you feel comfortable enough with that you could learn what you need to learn, and be willing to stand up again if there is a setback. Understand that you have a winning hand just because you are who you are, and go for it!Mentioned in This Episode:Productive FlourishingFreshBizThe New Entrepreneurz: Changing the Way You Play Life, by Ronen Gafni and Simcha GluckLeave a Review This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.productiveflourishing.com/subscribe

Ishita Gupta is a leadership and business strategist who was the head of media of the Domino Project for two years, and is a sought-after speaker. She joins Charlie today to talk about rebuilding her life and business. After a confluence of major life transitions, Ishita went home to refortify herself with her parents, only to realize her parents were in a health and business crisis that she needed to attend to.Key Takeaways:[4:20] - Ishita shares some of what she’s been challenged by in the last two years. She has been working as a business coach and publishing her online magazine for a while, but in 2015 she became very burnt out with her work - she was working a lot and feeling stressed and very tired. In addition to work stress, she was in an unhealthy relationship as well.[7:30] - This point became a big wake up call for Ishita to get away and slow down a bit. She moved back to Detroit with her parents, and realized her mom was having major health issues, which began to affect her mother’s business as well. At this point, she had to give up her own healing to focus on caring for and helping her parents.[11:55] - The last two years have given Ishita some of the biggest lessons of her life, and taught her to challenge some of the things she previously believed. These lessons include surrender, acceptance but not approval, and being okay with uncertainty.[12:53] - For the first full year, Ishita felt embarrassed by talking about her situation. This translated to the communication in her business and online presence; however, she did have her core support group to talk with, and she learned that everyone just needs someone to listen sometimes.[16:04] - In 2016, she had to stop her business for a period of time so she could take care of herself. Being real with her clients, and their understanding, was an important part of her healing process.[17:45] - Charlie shares his experience with a period of grief, and not really being able to share too much with other people. It could be helpful to just let other people know that something is going on, even if you don’t want to go into the details.[18:57] - Business stacks on life, not the other way around, and sometimes the business of life is the business. If you need someone to talk to, be careful of the people who are well-meaning fixers, when you may just need a well-meaning listener.[21:27] - One of the big lessons from Ishita’s story is that even when there were times she couldn’t perform, she still survived. If you’re at a point where your business pays the bills but you’re unable to make ends meet, let yourself off the hook for a period of time. It doesn’t always feel good, but you’ll be able to make it through.[24:21] - For the compartmentalizers, while it’s good that you can put stuff away to get through work or family issues, be aware that those things are stil there. But it is okay to give yourself permission to be going through a hard time.[27:00] - One of the challenges of entrepreneurship is when it becomes a self-aspirational label. This becomes a situation when your business is not working, and you can’t make a change as an entrepreneur. You’re not a failure if you have to get a 9-5 job for a period of time. Charlie shares four key points for people in a rut: know where you are, where you’re going, have a road map between those two places, and know what to do when your plans doesn’t match reality. Part of the challenge is accepting where you are right now, and being adaptable to change. Ishita shares some of her struggle with this, and how she was able to turn the situation around into one where she had the freedom to be herself. Moving forward, she will have all the lessons she’s learned in the last two years to add to her plan.[31:06] - Many people feel the most trapped in the areas where they have stuck their energies or minds. You have to give yourself permission to let go and focus on what other stuff needs to be done.[33:50] - Life can be good and hard at the same time. You have to learn how to hold on to the great moments in the middle of grief. Finding the people you can talk to about it, and being okay with what is, are the first steps in being okay with the shifts it could cause in your life.[36:15] - Ishita talks about struggling with finding a balance between oversharing to the point of too much information, and under-sharing where you don’t allow yourself to connect with your readers or listeners. For her personally, if she doesn’t share in some capacity, she won’t be able to show up for her clients in an authentic way. As you work through this for yourself, you’ll find what level of sharing is comfortable for you. For Charlie, the important thing is knowing how sharing can prevent you from or enable you to move forward.[40:07] - In your business or personal brand, what attracts people to you is your Achilles’ heel. If you cover up too much of your vulnerability, people might find it difficult to relate to you. The ownership of these vulnerabilities is important in sharing it with others and also claiming and taming it for yourself.[45:20] - Sometimes, it can be very helpful to escape from the reality of your hard situation and if you can, give that time to someone else. For Ishita, if she can still help someone and deliver results, she finds that it really helps her. The idea that you have to be in your perfect state to do your best work is a point worth challenging, and will be different for everyone.[48:11] - For people who may have more trouble compartmentalizing, it can help to identify the bad stuff, but then also look for the good stuff that fuels you and that you can use to anchor you throughout the day. Balancing the less favorable stuff with the nourishing parts of your life can help you navigate through the hard times. Breaking things down can help you focus on the things that are going to help you grow, and identify those that perhaps are not worth investing in anymore.[54:45] - Sometimes, it’s about making the situation suck 1% less rather than making it 1% better. Making progress on the good things as well as making progress on the bad things can provide us with additional motivation to keep moving forward.[58:10] - When you surrender in some way, that’s where solutions can start to come from.[59:00] - Ishita’s invitation for listeners: Recognize that your best work does not always have to come from perfect times. Some of Ishita’s best work has come from her messier moments. Make your mess your message - take ownership of your life, your lessons, and the way you want to share them with the world.Mentioned in This Episode:Productive FlourishingIshita GuptaThe Domino ProjectThe Progress Principle, by Teresa Amabile and Steven Kramer This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.productiveflourishing.com/subscribe

Today’s guest, best-selling author Vanessa Van Edwards, joins Charlie to talk about human interaction and succeeding with people. You might think that someone who writes about people is a raging extrovert, but that’s not always the case. Vanessa refers to herself as a “recovering awkward person.” In today’s episode, she and Charlie talk about how much they actually prepare and set themselves up to be comfortable in social settings, rather than leaving it to chance and charm.Key Takeaways:[3:05] - Vanessa shares a little bit of her background, moving from being a socially awkward person to someone who is writing books about winning with people. She talks about two different types of awkwardness: an inhibitive awkwardness that causes you to shut down around others, or an awkwardness that causes you to overcompensate when you’re around other people. She believes both are born out of fear, and it’s important to know which way your social fears will manifest themselves.[5:27] - Charlie defines himself as an ambivert, depending on the context. In a comfortable environment, he may appear as an extrovert, whereas in less familiar environments, he tends to be an introvert. Vanessa shares her personal experience with this at the World Domination Summit and what she did over the course of several years to make herself more comfortable in the context of this conference.[10:30] - If you’re an ambivert (or an introvert), it can be helpful to have some go-to questions that you can ask when you approach people in a social setting. Vanessa talks about preparation for events and conversations, and making plans that provide structure for the course of an evening or help to guide an interaction. Charlie recommends asking questions that don’t require too much personal vulnerability, but still allow the conversation to flow.[15:00] - When Vanessa was doing networking experiments for her book, she found that some questions really attracted extroverts, while the same questions could push an introvert into fear. The specific question in this case was “What’s your story?,” but regardless of the question, you have to be sensitive to how people will exhibit their social fears.[18:50] - If there is a question you don’t like being asked, you can prepare an answer that you’re comfortable with so if someone asks you, you can keep the conversation moving and gravitate into more comfortable territory.[20:50] - The swan effect is where something appears easy, comfortable, and graceful on the surface, when underneath there is a lot of work and preparation required to maintain that appearance.[25:07] - It takes time to get to the place you want to be, whether it’s in your business or a relationship, and that’s okay. Both Vanessa and Charlie can speak from experience that it takes a lot of hard work and not-so-glamorous preparation to get on the path to where you want to go.[29:12] - Before Captivate, Vanessa had written three books that didn’t do so well. Her first book was self-published and self-promoted, and she used her baby-sitting money to publish it. This one actually did relatively well, but gave Vanessa a little bit of a false sense of confidence. The second book was also self-published, but didn’t do as well. With her third book, she went with a traditional publisher, but there was no public response.[33:45] - It took five years for Vanessa to come back from this rejection of her book, but the fourth book was a turning point for her. During this time she wanted to blame other people, but she realized that she wrote the book based on what she thought the publishers wanted, not for her or her current readers. When she asked herself what she could write just for her and her readers, that’s where she found a pivot point.[39:07] - In Charlie’s writing experience, the book proposal was often a difficult obstacle to tackle. One of the worst ways to try to write a book is trying to write it to how someone else wants, rather than in a way that’s magical to you. Vanessa talks about the model for a platform that most people feel they have to follow. There’s a window in which you feel confident enough to write about a topic and be successful, but the idea is not yet stale to you. That’s the ideal window you want to be in.[44:18] - There are three options for publishing. You can self-publish, or if you go with a traditional publisher you can either get a small advance where the company has little stake in the game, or a large advance where there’s something in it for the publisher. In the case of a large advance, they may be more willing to help with marketing and support. You want someone to have their name on the line for you at the publishing house.[48:10] - Create the types of things that you want to consume. Just because you can create something, it doesn’t mean you should.[49:55] - How did Vanessa become emotionally prepared enough to go with a traditional publisher for her fourth book? She had advocates on her side who gave her confidence in herself and encouraged her to write what she wanted. She also felt that not having a book was preventing her from being able to help people.[54:45] - Vanessa found her business and personal sweet spot by adding structure to different areas of her life. It takes time to develop these things, but the payout is worth it.[56:35] - Vanessa’s challenge for listeners is to pick one event or meeting that you’ve been dreading, and come up with a purpose for it. Think about how you can set yourself up for success to achieve that purpose, and see if it changes the apprehension surrounding the interaction.Mentioned in This Episode:Productive FlourishingCaptivate: The Science of Succeeding with PeopleThe Science of People This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.productiveflourishing.com/subscribe

In today’s episode, Angela joins Charlie to talk about personal change. Most of the work that’s done at Productive Flourishing is around personal transformation and self-mastery. In Angela’s new coaching role, she’s been doing more and more of this with others. Charlie and Angela share some of the changes they’ve made in their personal lives over the last year, and how their relationship fits into how they navigated these changes.Key Takeaways:[2:05] - For Charlie, the impetus for personal change often comes from something specific that has happened in his life, and figuring out what he can do to fix it. He is constantly changing and working on things, and likes to experiment with them in his own life before he shares them with others.[3:15] - For Angela, she sometimes lets things get really painful (physically or emotionally) before she makes a decision to change and follows through with the decision.[5:32] - Charlie talks about the dynamic in their house; both Angela and Charlie are coaches and empathetic people, so they’ve had to learn how to constructively invite change dialogue into their home life outside of their work. Attentive listening, thoughtful questions, and knowing the right time and context to bring up issues of habits and change help to guide their discussions.[10:00] - One of the most counter-productive things you can do is trying to get someone to change when they aren’t ready, and they don’t want support.[12:50] - Charlie shares a time where his daily work was presenting a type of pain or discomfort. For Charlie, working too much or too long was causing him to feel more and more pain.[17:52] - The Kaizen approach encourages incremental, small changes over time that add up to a big effect. The trick is knowing whether it’s time to take an incremental step or tip over an edge with a big change.[20:25] - When Charlie began noticing pain, he started to incorporate 30 minutes of movement each day, and also invited daily writing into his practice. This spurred some adjustment to his schedule so he’s only working 8 hours a day, which has affected not only him but Angela and the team as well.[28:15] - It is important to consider how the changes will impact those around you. For Charlie, he is still uncertain and nervous about how his new practices might interfere with the relationships he has with people. Being aware of what conversations might need to happen in the face of change is important so that you can create and maintain boundaries.[34:05] - Charlie introduces the five keys to managing change, which will be the focus of the next book he’s writing: intention, awareness, boundaries, courage, and discipline.[37:50] - Angela shares some of the personal changes she has been making throughout the course of the last year. One of the main changes is centered around weight and diet. In February, she made a pretty dramatic change and went on a diet that helped change her metabolism. This was an important change because it would affect not only Angela, but Charlie as well.[42:35] - He started out on the diet with Angela out of solidarity, but also had to learn a balance between encouragement and looking out for Angela’s best interests.[47:50] - When you’re in relationships with people, some of the things that matter the most are the most awkward to talk about.[50:36] - It is important to note that everyone will experience and handle personal change differently, based on your life experiences. Not everyone’s journey is going to be the same when it comes to the difficult, but it is important to make sure you’re on the right road for you.[55:14] - Charlie’s invitation/challenge for this episode: Think about what incremental steps you could start taking today that would make your life a little easier. Starting with a small change can build the foundation for making other changes that could have a big payoff over the course of a year. Is there a big change you could make?57:28] - Angela’s invitation for this episode: Be gentle - be kind with yourself, and make a purposeful decision about what it is that you want to change.Mentioned in This Episode:Productive FlourishingWhat Do You Need to Form Healthy Habits that Stick?, by Charlie GilkeyThe Two Dynamics of Change, by Charlie GilkeyLeave a Review This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.productiveflourishing.com/subscribe

Michael “Gebbs” Gebben joins Charlie on today’s episode. Michael founded Gebbs TV only to realize he was building something that was making him miserable. After reconfiguring his business to work for him, he realized that he had a major problem: his use of credit cards disguised his understanding of the success of his business and led to debt. The conversation today centers on the prisons we make for ourselves, how easy it is to build these prisons, and how hard it is to break free of them.Key Takeaways:[2:35] - Growing up, Gebbs had always had an entrepreneurial streak, and combined with his background in filmmaking, he got a job making slideshows for funeral homes. This sparked the idea for Gebbs Total Production. As the company began to grow, he realized that the filmmaking aspect was more his dad’s dream and he wasn’t really into it. He found himself low on time, low on money, and very behind in delivering product to his clients.[7:15] - He decided to narrow his focus and took a stand on the way he wanted to do things, and that’s when things started to happen. By not agreeing to do everything (just because you can), and doing the things you’re best at, people will honor that. This exposes your ability to make a decision, your ability to be a pro, and your ability to be the best in your local world.[10:50] - These days, the product is not usually the most important thing. The differentiation starts to be the person behind the product. Gebbs shares his example of people paying more or bringing him on location for a video, versus someone local, because they like the substance that he himself brings to the job. You can’t win on pixels - or whatever medium your product delivers - but you can win on process, experience, and expertise.[17:25] – Gebbs and Charlie talk about the importance of taking action - it brings clarity and confidence. Getting your product out into the world allows you to receive feedback from consumers. Finishing allows for mastery as well as income.[20:05] – When Gebbs found the sweet spot with Gebbs Total Video, he found success, freedom, and time to do the things he loved. The process of becoming self-aware allowed him to break out of the prison he had made for himself by taking on projects that he wasn’t excited about, resulting in mediocre product. Identifying the root problem allowed him to prevent the same surface problems from showing up.[25:40] – There is a lot of hard work that goes into running your own business. Oftentimes, when people start their own businesses, they start as an expert in their trade wanting to do more. Starting your own business adds many other factors in addition to the trade, sometimes leaving only a small amount of time to actually do your trade. Being self-aware of what works for you is important to figure out what option will let you flourish doing what you love.[31:20] – Personal development is more like a corkscrew, rather than a circle. We might encounter similar problems throughout the different stages of our lives. Each time we come back to them they are at different and deeper levels. Problems and challenges will always arise, and you will continue to be challenged and tested by similar things, though maybe in different ways. Accepting and embracing this is important to overcoming those challenges and being ready to face them any time they arise.[35:50] - How you deal with challenges is totally different when you’re aware of them. Being self aware also allows you to help and encourage others when they encounter similar difficulties. When you find the sweet spot, you get more time and freedom to spend your energy on the things that matter.[42:00] - When you become aware of your patterns and blind spots, you can build life support structures around those things, so they are not always crippling. If you want to change these patterns in your life, you have to ask yourself how you are actively participating in those scenarios, and which ways you are showing up in those scenarios. This allows for greater self-reflection about the root of the problem.[47:40] - Gebbs talks about how he found himself in a large amount of debt, and how he is now working to overcome it. He was charging everything on credit, and needed more money than he was making to pay all his bills. As he figured out a way to work to pay off the debt, he recognized a deeper problem and has been able to make changes to avoid finding himself in a similar situation down the road.[55:55] - Being able to talk about this has allowed Gebbs to feel a new sense of freedom. Talking about it - without being judged - allows for ideas to be shared and to find people who have encountered and overcome these problems. Financial intelligence is especially important for entrepreneurs.[1:00:40] - Scripted formulas and frameworks are not the simple solutions to the challenges we are going to face. Success takes hard work, not just in your business, but also in taking ownership of ourselves and our habits, and identifying the root problems. It is takes awhile, and that’s okay.[1:08:20] - Gebbs’ challenge for listeners: If there’s something that you’re afraid of doing, just take the first step. Once you do that and experience that release, it gets easier and easier each time.Mentioned in This Episode:Productive FlourishingMichael “Gebbs” GebbenGEBBS TVLeave a Review This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.productiveflourishing.com/subscribe

Jeffrey Davis is the founder of Tracking Wonder, a consultancy that mentors entrepreneurs, creatives, and brands to have influence with integrity. In his third appearance on the show, he and Charlie discuss why it’s so hard for leaders to stand for something, even after they’ve figured out what it is they stand for. It’s not just the fear of failure or being wrong. This episode is a continuation of ideas presented in a previous episode - to hear more after this, check out Episode 64.Key Takeaways:[3:25] - Some of the fears people have about standing out with their message is that they may be attacked, or lose clients and customers. The second one, more subtle, is that once you take a stance and it’s said out loud, the expectation is that you have to deliver on it.[5:28] - With regards to the first fear, it is often a false belief that the trolls and haters will all of a sudden pop up and latch on to you. You might end up alienating a few people in your audience, but there are many other people that won’t notice or care. If you do attract opposing views, rather than viewing it as battle, use it as an opportunity for conversation. People who question a view or are curious can become your allies if you engage with them in a certain way.[10:09] - Owning a message or taking a stance doesn’t mean that the ideas or stances are politically loaded or controversial. Sometimes, just the idea of taking a stance is controversial in itself . This is especially applicable in the corporate world to intrapreneurs and people working within corporate organizations.[13:30] - There are certainly conversations to be had about taking a stance in the corporate world, but there are other topics in that realm that aren’t socially loaded. In terms of productivity, if at a certain point in your development you’re not finding places that are controversial in the sense that different experts disagree on them, you might need to do some more deep exploration to develop your own opinions to help you stand out and make an impression. Opposing ideas can create new ideas.[16:26] - You can begin to develop your own thought leadership by mining and leveraging your irritations. You can take an idea that’s out in the world that you find irritating, and come up with the opposing idea that you want to contribute. This requires some deep work - owning your message is not just what you stand for, but what you stand against as well.[19:25] - One of the reasons people fear standing out is because they don’t want to be the outlier or be ostracized. However, with the myriad of ideas in the world today, there are other people that are bound to share those beliefs or take the same stance. It is beneficial to surround yourself with a small group of people where you can try out your own ideas (and others).[21:15] - Some of Jeffrey’s advice is to read what other people (professors, leaders) have to say about a certain topic, and then see where you can add your verse to the conversation. Start testing out your ideas and find where you can gain traction. That is how you begin to stand out by trial and error or experimentation.[26:58] - Another reason people are afraid of standing out is because they might be wrong, in two ways: if what you thought was true is not true, or what you thought mattered most to you has changed. But if you’re wrong, that’s okay! You can take a stance and be right, or take a stance and be wrong, but both provide opportunities for exploration and growth. The only trajectories not worth taking are to not do anything, or perpetuate what you already know.[30:15] - One thing Jeffrey suggests for people with a plethora of ideas is to distill your ideas down to a smaller number. When you start to narrow what you’re going to be about, you’re forced to go beyond just your initial opinion.[32:20] - Another fear is that people don’t want to stand for a message because they don’t want to lock themselves into an idea box. When you find yourself fatigued with an idea or what you are associated with, tap in and see what’s fresh, and how you could turn that into a new stance.[37:30] - As human beings, we have complex dimensions of being in the world, and we should have the permission to be our complex selves. People want complexity now, versus a generic brand that blends in.[39:15] - As you stand for more and begin to produce more, you have to become a curator as well as a creator. The fears that have been discussed may stem from wanting people to see the rich person that you are. However, it’s important to note that your work does not encompass all of who you are. It can be a vehicle of expression, but there’s often more that is not represented. In addition, you may choose to represent or incorporate some aspects of yourself into your work, while intentionally leaving out others.[47:00] - Developing constraints in our work allows for depth and experimentation within those constraints. This can allow you to hone your work and create a niche for it. Go in depth in certain areas, rather than trying to cover multiple areas.[52:25] - Charlie and Jeffrey talk about the importance of creating for the future. Sometimes, it can be hard to set expectations for immediate response, but the work that stands out will continue to be relevant in the long-term.[54:25] - If you’re not standing up for your message, then other people are only hearing counterproductive messages. Your silence only perpetuates whatever conversation you don’t like.[56:45] - Jeffrey’s invitation to listeners: draw a chart with for and against, and at the top write what it is that you want to be known for. Under “for,” list variations and values that relate to the core message. On the right side under “against,” list the counter-messages and values that you’re against that relate to that core message. He challenges listeners to share something about that in the next 7 days.Mentioned in This Episode:Productive FlourishingTracking WonderProductive Flourishing Podcast Episode 64: What Will You Stand For This Year?Leave a Review This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.productiveflourishing.com/subscribe

Michelle Jones, founder of the Wayfinding Academy, joins Charlie on the show to talk about the college experience for students at the Wayfinding Academy. Instead of spending two to four years taking classes and then figuring out who they want to be in the world, students learn to live life on purpose and then use that knowledge to sculpt their learning experience. One of the members of the first group of students, Austin Goldberg, also joins Michelle and Charlie to share his experience.Key Takeaways:[3:40] - Michelle shares the story of Wayfinding. Michelle had been working as a professor for 16 years, and she began feeling that the way higher education worked was backwards. Generally, students were asked to make decisions and determine plans up front, without getting a chance to discover their purpose until they were already finished. About two and a half years ago, Michelle decided to quit her job as a professor and start her own college to flip that experience around. At Wayfinding, they start with the questions first and determine what students want to do in the world, and how students and faculty can work together to figure out the steps to achieve it. When they leave Wayfinding, students know what they’re doing and in most cases are already doing it.[7:40] - In higher education, there seems to be a front-loading of the question “What do you want to do?” Often times, this makes students have to choose an occupation rather than focusing on who they want to be in the world. At Wayfinding Academy, students receive their Associate’s Degree in “Self and Society.” Throughout their education, students explore who they are, as well as what is going on in the world, and the goal is to figure out how they can put those two things together in a meaningful way. From there, it is presumed that students will figure out a way to earn an income in a way that supports the life they want to have.[9:40] - While there may still be career pivots in the adult journey of those students, Wayfinding helps students learn how to ask the appropriate questions to figure out how to navigate those transitions.[12:23] - At Wayfinding, they focus on the six character traits outlined in their promise:Empowered to thrive throughout the rest of their lives 2. Embrace curiosity 3. Willing to stretch 4. Understand the importance of conscientiousness 5. Know how to create community and 6. Understand what it means to live life on purpose.[13:37] - Within those character traits, they identify 10 learning objectives, some of which are, how to ask good questions, how to be a good critical thinker, how to collaborate, why story matters, what it takes to do something epic, and how to make a plan for something hard that requires other people’s help. These skills are transferrable no matter what students choose to do.[15:53] - As the Chief Academic Officer, Michelle has been collecting data to gauge the effectiveness of the program and students. When they started looking to hire additional crew members, they began to examine what qualities they expect of their staff and how that overlaps with what they expect of their students. This helped to shape their promise.[19:20] - Austin shares his experience about discovering and getting started with Wayfinding Academy. When he was approaching high school graduation, he was on the traditional trajectory to graduate and go to a traditional college. He talks about the events of the first year of his college experience that made him start to question and evaluate his place there.[23:20] - Austin talks about how it was difficult to choose something other than the trajectory he was already on, but he knew the environment at the private business school wasn’t for him. He started to look for people and places that cared about the things he cared about, which is how he ended up in Portland and discovered Wayfinding.[25:52] - One of the great things about Wayfinding is there is a lot of freedom to do the things you want to do and discover the things that you’re interested in. For Austin, he has been able to discover how to express his creativity. He states that this vulnerability is also some of the hardest work they do at Wayfinding. The most important thing he’s learned about doing this type of work is that no matter what the outlet is, it’s going to bring to light the same issues and challenges Austin (and all students) faces in life, because it tests personality traits more than occupational traits.[31:00] - One of the fundamental aspects of Wayfinding is that when you live your life on purpose, and do work purposefully that matters to you, all your “stuff” does come up. Charlie talks about one of the labs he taught at Wayfinding, and Austin shares his experience working through the project of that lab, what he learned from it, and how it has carried over into other aspects of his life.[36:15] - One of the big projects Austin has been working on during his time at Wayfinding is figuring out what it means to do something epic or live an epic life. He speaks about what he has learned about this during his experience so far.[40:07] - Michelle talks about some other students’ journeys. Student cohorts are made up of a diverse age range, but they all focus on living life on purpose and being in a supportive learning community as they figure that out. The Wayfinding experience seems to work equally well for people who have a small idea of what they want to do with their lives and people who have no idea.[45:24] - Michelle discusses the guide program at Wayfinding. This was an aspect that couldn’t truly be tested until they actually had students, but they’ve done some experimenting to figure out what seems to work. Developing the guide program has also opened conversation with the students to help shape the role of the guides.[52:06] - Michelle and Charlie talk about some of the unique aspects of figuring out the systems within such a dynamic program. It has been a process for the faculty and students alike to determine what is going to work best for their program.[55:45] - Austin’s invitation for listeners: Look for areas in your life where you are doing things a certain way just because that’s how they’re done, and challenge that. You don’t always have to do things one way just because that’s how they’ve always been done.[57:01] - Michelle’s invitation to listeners: If after listening to today’s episode, you were inspired by or desire to be a part of this program, reach out and start a conversation! The next cohort starts on August 28th, and they are always looking for new friends, fans, and supporters.Mentioned in This Episode:Productive FlourishingWayfinding AcademyLeave a Review This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.productiveflourishing.com/subscribe

Larry Robertson, author of two award-winning books, joins Charlie on the show today to talk about growth, creative edges, play, uncertainty, and how our relationship with our work changes the longer we do it. This episode is a bit of an extension of a post Larry wrote for Productive Flourishing.Key Takeaways:[2:12] - What do we do when we come up to a growth edge when we’re out in creative exploration? When the curiosity and wonder stops fueling you, you can get stuck because you’re afraid or don’t know how to move forward. Larry is going to share his three growth-oriented ways to tackle this, and give some examples at different levels.[3:45] - There is always going to be an edge between what you know, and what you will soon know. What’s interesting about those places is that we’re drawn to them - whether there’s something more we’d like to know, or there’s something more we can do better or do differently. Larry suggests that we may be fearful as we approach these edges because we feel that once we cross over the edge we’ll have to understand everything right away, or we’ll have to take a giant leap into something new. It is okay to make it a habit rather than a solution, as you continue to cross and work toward new edges.[6:25] - It is important to recognize and understand that we can still push the edge while investing the time to become masterful at something. It’s not an either/or action - these are things you can do simultaneously. Additionally, you can grow your edges outwards to include new fields, or grow your edges deeper into a field you’re already invested in.[8:45] - Oftentimes we may feel like our environment is putting us in a position that we either have to be in control, or we have to be creative. The irony is that we’re always both; the balance is different for each person, and for each person it’s different at different times. Having “certainty anchors” can ground you to the certain parts of your life as your explore the unknown edges.[12:30] - How do you approach the edge between the known and unknown, and what do we do once we get there? Some different ideas include starting from your anchor to explore something new, asking questions to figure out how to explore something new or going off the edge, and exploring new territory with those certainty anchors that remind you where you’re headed and why you’re heading there.[14:28] - Charlie adds a fourth piece: a mindset piece. When we are exploring edges, it’s okay that we don’t know, and we have to be comfortable with not being competent at some points. This gives us the freedom to stumble as we’re moving forward, without worrying about the consequences. Larry talks about “lucky people” and how they approach these edges with a sense of playfulness.[19:32] - Charlie shares an example in his own life about joining the board at Social Ventures Partners. Many people think they are going to regret the decisions they make or the things they do, but more often than not, people regret the times they could’ve explored the edge and did not. Larry shares the examples of Larry Bird and Magic Johnson and how they used this philosophy during their basketball careers and their pursuits after.[24:18] - Charlie reflects on his stories since he resigned from the military, and how this has affected his strategic plays - they are more long-term rather than quick, in-the-moment decisions. Once you get to a certain point, most of your adventure is long-term creative and social exploration.[26:45] - Many of us start in a scenario where we’re “young” - whether that be in age or in our career. Whenever we’re young at something, we tend to see things in a shorter way, so our targets are about the most immediate success we can define. We lack the experience that comes from spending more time in something. Larry relates this to his changing role as a parent as his son gets ready to go to college. How we mature as thinkers and doers changes the game, but it’s a good thing.[32:15] - In many careers, when you’re new, you’re fueled by the curiosity and passion of doing the process. After you’ve explored the easy wins, there’s a deeper level of mastery to achieve. There’s always going to be the edge of what’s familiar and what’s unfamiliar.[34:12] - When what we are doing becomes an ongoing excuse, rather than something that fulfills you, it may be an indicator that we have arrived at an edge. In these instances, we must shift forward and look at things in a different way to see how we can expand on it or beyond it. This is when we have to pursue questions to find out what we haven’t yet discovered. This is our “fit sense.”[36:52] - There are also “depth check” questions we can ask ourselves - are we looking at it too deep or too shallow, or is there somewhere in between that we need to be exploring? There is such a range of questions you can ask, because at the end of the day, it’s about an inquiry mindset that keeps asking.[39:45] - We can get into a rut where we ask questions that are too deep, based on wrong signals.[42:00] - In our fields, when we switch mediums or presentation styles we might feel like it’s super hard. On one hand, we crave doing something novel, but on the other hand, we fear not being good at something. However, it’s okay to find out you’re not good at something. We start to think of our total way of doing as our certainty anchor, rather than a few important things to latch on to. All of us get caught in these places where we think we’re being open-minded, when what we really need to do is go a little bit further and be open in a broader sense so we’re not anchored down in a negative way.[46:33] - The 3 Growth-Oriented Ways to Explore Your Creative Edge: 1) Choice: In everything we do, there is a choice - even within your pre-existing patterns. There is power in this choice. 2) Reaction: When we get results back from making our choice, how do we react to it and why? 3) Improvisation: When we get to the edge, we’re going to have to change the way we do things in some way. If we remember that we have the choice, and that we can consciously react rather than having a knee-jerk reaction, and realize that we will have to improvise, we actually make ourselves more powerful as we move toward new things.[49:40] - Not choosing is itself a choice. We have a tendency to think that anything different than the status quo is a choice we have to make. But maintaining the status quo is also a choice. We can choose to remain on the comfortable side of control, or we can choose to do something different. Compare the positives and negatives of each choice to the other. When we learn to do that, we see that we’re always at an edge.[52:45] - These three growth-oriented ways serve as capstone to the whole process of approaching the edge. It is continuous - there is always a new beginning but it’s all part of a cycle. No matter the rewards, it will always involve choice, reaction, and improvisation. Charlie and Larry talk about approaching these choices with a mindset of playfulness.[57:32] - Larry’s challenge for listeners this week is called: Change the Question! Instead of saying “why?,” say “what?” or “how?” Think about a question that you’re faced with at work or as you move toward an edge - change that question to use a different prompt and see how it gets you thinking differently.Mentioned in This Episode:Productive FlourishingBooks by Larry RobertsonProductive Flourishing Podcast Episode 131: Questioning the Givens of Creativity with Larry Robertson3 Growth-Oriented Ways to Explore Your Creative Edge, by Larry Robertson on Productive FlourishingUncertainty, by Jonathan FieldsStop Lying and Start Creating, by Charlie Gilkey on Productive FlourishingWorld Peace and Other 4th-Grade Achievements, by John HunterLeave A Review This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.productiveflourishing.com/subscribe

In this episode, Angela joins Charlie to discuss how they are balancing service work and volunteerism within their personal and professional lives. Both Charlie and Angela have taken on new commitments with various organizations, and they’ve been examining how much time they’re giving to service and volunteerism, as well as making some important decisions about what those boundaries look like.Key Takeaways:[1:38] - Charlie and Angela talk about the new commitments they’ve taken on - in many cases within organizations they had already been previously involved in. Their boundaries for what they can take on are being tested as these new commitments displace other things. They have had many conversations about how much time they’re giving to service and volunteerism, as well as taking a hard look at those boundaries.[4:18] - At the Wayfinding Academy, they are flipping the college experience on its head - it starts by focusing on students first and who they want to be in the world, and helping them cultivate themselves and their next steps needed to be that person. Charlie has recently become the board Chairman within this organization. His work with Social Ventures Partners, where he is also on the board, focuses on bridging the gap in Pre-K education for minority populations.[6:45] - Angela has also taken on a new role within the Wayfinding Academy, as Chairperson of the Wisdom Council (Charlie’s old position). In addition to this work, she is involved with the board of a women’s spiritual community in Portland, serving as the right-hand person for the spiritual leaders of that community. This commitment is twofold; in addition to the administrative commitment, there is also a spiritual commitment.[9:15] - Angela talks about why they are involved in these acts of volunteerism. In addition to it just being part of who they are and what they do, there is a big focus at Productive Flourishing on community integration. It’s a great quality to have to jump all in with the things you’re involved in, but sometimes you may get into a situation where you jump in too fast. Charlie and Angela keep this under control by checking in with each other on boundaries and making sure these commitments are aligned with the work they want to do in the world, while continuing to take care of themselves.[12:43] - Charlie talks about value (both economic and otherwise) and how that can guide our decisions about what we’re involved in and continue to do. He also talks about Proactive Activism: a strong civic involvement to help bridge the gap between the public and private spheres. Instead of just preaching, they get involved because they want to model the message as well as sharing it. For them, a big focus is education, as it is a pathway to equality.[15:55] - Finding institutions that advance your political or social priorities is really important. Charlie and Angela talk about the personal reasons they have for choosing their particular organizations to be involved in, and what it means for them to be involved in those organizations now.[21:50] - Charlie talks about their involvement on the boards of their organizations - both Charlie and Angela don’t like to be passive in an organization, and being on the board allows them to be in a high-leverage scenario to make the the most impact. These positions also fit their specific skill sets. Additionally, they both prefer greater involvement in a few organizations rather than spreading themselves too thin across several organizations.[25:55] - Integrating volunteerism and service into business: How do these organizations further Charlie’s professional and personal development? For Charlie, these organizations are a natural outgrowth of the people he’s involved with in the community and embody who he is as a person. It has been challenging to incorporate the results of his involvement professionally, because the leadership is more committee-based rather than the type of leadership he would use for a small business. Although it has challenged him, it’s been a good learning period.[28:53] - Your business can’t fuel all parts of you - volunteerism and service provide another context for leadership and taking on big goals.[31:25] - In addition, having these extra involvements has made Charlie more intentional with his business work with Productive Flourishing. It has also made him more intentional about spending his extra time to further Wayfinding Academy and Social Venture Partners (SVP), rather than killing time on Facebook or something that is not as fulfilling. Charlie has experienced a lot of personal growth.[36:00] - Angela shares her experience of how volunteerism and service have influenced her personal and professional growth. She feels that her leadership skills have been tested and challenged, and have gotten better in the past few years. She has also gotten more comfortable speaking up and using her voice to make her perspective clear. Being able to use her past experiences in her new contexts has allowed her to better show up with her work with Productive Flourishing. Her work with Productive Flourishing, Fourteenth Moon, and Wayfinding Academy seem to feed each other.[39:11] - In Angela’s work, she has been challenged by engaging in and facilitating hard questions and conversations. It has been an interesting development for Angela, but she’s been able to take the ability to facilitate tough conversations in her personal life into other areas, like Productive Flourishing and her council and board work. This is an excellent example of the benefits of being involved in civic organizations; they can help you develop skills you may not have otherwise developed. In addition, it gives you an additional avenue to cultivate and practice these skills.[44:10] - Being involved in outside organizations also allows you to keep your growing pains and strife outside of your personal relationships. Keeping those aspects in outside organizations that are in service to your community is a good way to build synergy and a good life where you are able to grow and develop in service to other people.[45:17] - There can be some downsides. Investing your emotional energy into external or volunteer organizations can decrease it in other areas. It is important to find a balance and make sure you have ways to “fill your cup” as it becomes depleted. Angela and Charlie both speak to the fact that working through these challenges themselves has allowed them to help other people with them as well.[49:44] - Charlie describes the effects of their involvement in these organizations as catalytic, both in business and in personal life. It has allowed for new growth and awareness. We don’t always realize what we can do and who we are in a lot of ways until we have the external situations that reflect those things back to us and give us a mission, trial, or opportunity to play out what we can do.[50:55] - If you’re looking for ways to thrive and flourish in the world, find places to volunteer or be of service in your local community, and align those things with the ways that you want to grow.Mentioned in This Episode:Productive FlourishingWayfinding AcademySocial Venture PartnersWomen of the Fourteenth MoonDemocracy on Trial, by Jean Bethke ElshtainBowling Alone, by Robert PutnamLeave a Review This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.productiveflourishing.com/subscribe