Summer is in session but we’re not taking off! Throughout the season, we’ll be bringing back listeners’ favorite episodes from past seasons and answering brand new Office Hours questions! Today’s episode from season 2 (originally released at the height of the COVID-19 pandemic) features Cait Lockwood (formerly Caitlin Pyle), founder of Work-at-Home School and Proofread Anywhere, talking about how she went from being fired from a job to building a seven-figure company she could run from home. Listen to this great conversation about how you can build your own business without leaving the house—even if you’re already retired. In this episode we’ll talk about: Remote work and unemployment during and after the COVID-19 pandemic Cait’s journey from being fired to building two businesses Discovering the viability of full-time freelance work What it takes to be entrepreneurial and create your own company Advice for someone looking to change careers or generate additional income The three-step system for success as a freelancer Identifying the lies we’re programmed to believe that can keep us from reaching our full potential Breaking past the self-doubt that can hold you back and replacing them with truths Abundance mindset vs scarcity mindset Leveling up by identifying existing skills and learning new ones The importance of confidence in successfully launching as a freelancer Changing the way we see retirement and throwing out conventional idea of retirement The reality of fixed income and how you can un-fix it Thinking outside—or breaking out of—the box you’re in to make more money and reach financial independence Inflation rate and how it affects retirees and seniors more than the rest of us The main things seniors spend money on – leisure, health care, education for grandkids, and scratch-off lotto tickets The investment of online courses for building new skills Millennials, participation trophies, and accepting failure as a lesson Vetting online courses and creators and filtering out scams Understanding affiliate marketing and how you can use it to make commission income Using social media and your existing networks for market research and finding clients Visit dontretiregraduate.com for a full transcript of this episode. Learn more about your ad choices. Visit megaphone.fm/adchoices

In today’s Office Hours, Eric answers Jenna's question: “how much should I have in an emergency fund?” This can vary based on a lot of factors, and emergency funds don't need to just be in the form of savings accounts. Eric explores the different layers that can make up your emergency fund and the rules of thumb for how much money is safe.  Have a question? Tweet it to us at @BrotmanPlanning or post it on our Facebook and it may be used in a future episode of Office Hours! Learn more about your ad choices. Visit megaphone.fm/adchoices

Welcome to the season four finale of Don’t Retire... Graduate! We’ve had amazing guests this season and couldn’t be more excited to finish with today’s guest. Dr. Daniel Crosby is a psychologist and behavioral finance expert who helps organizations understand the intersection of mind and markets and explores the way our brains affect our choices when it comes to money. He is here to talk about the way mental biases can affect our decision making and make us uniquely stupid when it comes to money (his words, not ours).  In this episode we’ll talk about: •Behavioral finance and looking at the role psychology plays in our financial lives  •How people are uniquely stupid when it comes to money and how the brain reacts when thinking about money •The biases we all can fall victim to that can negatively affect our investments  •Decision making styles applied to money versus everywhere else in our lives •The performance of Amazon stock over the past twenty years •Day trading and how active investors tend to underperform  •Action bias, confirmation bias, investing alongside your political party, investing alongside your morals, loss aversion, the house money effect, and mental accounting and how they all affect our financial choices  •The value of a financial advisor versus doing it yourself  •Results of studies on financial advising, including investors working with advisors accumulating far more wealth than those without advisors  •The meaning of the term fiduciary and how it applies to finance and psychology  •Giving up on dreams of professional sports careers •Positive psychology, PERMA, and Dr. Martin Seligman’s contribution     Visit dontretiregraduate.com for a full transcript of this episode. Dr. Crosby's Book  About Daniel Crosby Dr. Daniel Crosby is a psychologist and behavioral finance expert who helps organizations understand the intersection of mind and markets. Dr. Crosby's first book, Personal Benchmark: Integrating Behavioral Finance and Investment Management, was a New York Times bestseller. His second book, The Laws of Wealth, was named the best investment book of 2017 by the Axiom Business Book Awards and has been translated into 7 languages. His latest work, The Behavioral Investor, is a comprehensive look at the neurology, physiology and psychology of sound financial decision-making.   https://www.standarddeviationspod.com Learn more about your ad choices. Visit megaphone.fm/adchoices

In today’s Office Hours, Eric answers Jason's question: “what are a few basic aspects of a financial plan that I can create myself?” The truth is, you can do it all yourself or with the help of a few vendors. A financial planner is not necessarily needed. But which way is right for you? Have a question? Post it in the comments, tweet it to us at @BrotmanPlanning, or post it on our Facebook and it may be used in a future episode of Office Hours! Visit dontretiregraduate.com for a full transcript of this episode. Learn more about your ad choices. Visit megaphone.fm/adchoices

Welcome back to Don’t Retire... Graduate! Today we’re going back to school with Rob Phelan, a high school math and personal finance teacher and author of the children’s book M is for Money. Rob is here, live from his classroom, to talk about money and the roadblocks we’re facing while advocating for personal finance education for kids.  In this episode we’ll talk about: •The difference between math and personal finance  •Why we overestimate our abilities in nearly all aspects, but doubt our abilities to understand and make money •Money stories and how we’re shaped to make decisions as children •Why it’s so hard to create a formal education in personal finance •The struggles teachers face when creating personal finance curriculums •Nonprofit organizations that have resources available for schools and students  •How kids can start learning about money as early as preschool and how we can teach money concepts at different ages •Entrepreneurship, pre-selling a business idea, and crowdfunding •Understanding regret and buyer’s remorse as a child •The ice cream theory of teaching patience and delayed gratification to toddlers Visit www.misformoneybook.com to learn more about Rob's book.    Visit dontretiregraduate.com for a full transcript of this episode. About Rob Phelan Rob Phelan is a high school math and personal finance teacher in Frederick, Maryland, a Certified Financial Education Instructor, business owner, and author of the recently published children’s book, M is for Money.  Rob is a passionate advocate for greater levels of financial education to help our youth make better financial decision moving into their futures.  Rob Phelan Facebook Rob Phelan Twitter Rob Phelan Instagram Rob Phelan LinkedIn Learn more about your ad choices. Visit megaphone.fm/adchoices

In today’s Office Hours, Eric answers Matthew's question: “is it better to pay over the asking price for a house or just rent?" There is so much going on in the market right now that is making purchasing a home -- especially your first home -- particularly difficult and expensive. Do you go for it or wait it out? Have a question? Tweet it to us at @BrotmanPlanning or post it on our Facebook and it may be used in a future episode of Office Hours! A full transcript of this episode can be found at dontretiregraduate.com. Learn more about your ad choices. Visit megaphone.fm/adchoices

Welcome back to Don’t Retire... Graduate! Our guest today did what nobody thought was possible: left Eric speechless. Sharita Humphrey has a remarkable story of grit and resilience. From a homeless mother of two living out of a motel, Sharita promised her sons that she would change their situation and did not rest until she did. The now award-winning financial educator is here to share that story and spread her message that just because you lose things, you can never lose hope.  In this episode we’ll talk about: • The importance of having money conversations at home  • Sharita’s story of becoming a mom early, the feelings of failure that came with losing her home, and her experience living in a motel for close to a year • How financial literacy education can change your financial trajectory  • How it feels to leave traditional employment and scratch an entrepreneurial itch • Keeping experiences as a line item on a budget  • Creating a safety net by building an emergency fund  • Creating jobs and abundance through agriculture  • Seeing your budget as a blueprint to keep you in the driver’s seat     Visit dontretiregraduate.com for a full transcript of this episode. www.sharitamhumphrey.com www.changeinmotion.co About Sharita M. Humphrey Sharita M. Humphrey is a nationally recognized, award-winning finance expert and money mentor. Having previously been broke and homeless herself, Sharita knows first-hand that financial freedom has a blueprint and she’s committed to helping individuals change the financial trajectories of their lives.   Sharita is a certified financial educator, speaker, and coach. At her namesake financial consulting company, Sharita helps minority women better understand, manage, and grow their money. Sharita also helps Black and Brown entrepreneurs learn how to accelerate their businesses and secure funding through her other company, Change In Motion, which offers a comprehensive education program.   In 2020, Sharita was named National Financial Educator of the Year for her work within her local community and across the country. She is a regular contributor to entrepreneurial publications and has been featured in top-tier media including CNBC, iHeartMedia, Forbes, Yahoo Finance and BBC World News.   This year, Sharita and her family set a goal of purchasing hundreds of acres of land over the next few years to build a family-run farm. During their journey, Sharita is teaching minority farmers how to obtain monies to acquire farmland and helping them to retain their land for generations to come.   Sharita M. Humphrey Facebook  Sharita M. Humphrey Instagram Sharita M. Humphrey Linkedin Learn more about your ad choices. Visit megaphone.fm/adchoices

In today’s Office Hours, Eric answers Mark's question: "if you won the lottery and had the option of $30 million upfront or a million dollars a year for 30 years, which is actually the better option?" Unfortunately this is not a circumstance many of us will see ourselves in, but let's talk about it anyway. What are the realities of winning the lottery? Have a question? Tweet it to us at @BrotmanPlanning or post it on our Facebook and it may be used in a future episode of Office Hours! Visit dontretiregraduate.com for a full transcript of this episode. Learn more about your ad choices. Visit megaphone.fm/adchoices

Welcome back to Don’t Retire... Graduate! We have a very fun episode today and couldn’t be more excited to have Emily Guy Birken here. She is a lifelong money nerd, award-winning writer, and the co-author of STACKED: Your Super Serious Guide to Modern Money Management, written with longtime DRG friend, Joe Saul-Sehy. Emily joined us to talk about how to look at your money like a game of Tetris, the way gamification can be a powerful tool for change, and, of course, to set the record for the number of times “hemorrhoid” has ever been said on this show.  In this episode we’ll talk about: • Emily’s goals for every day • How to see your finances as a Tetris game and use it to help with budgeting  • How an emergency fund is the Easy Spin of budgeting  • Taking control of your money rather than seeing it as something out of your control • Gamification of money and when it is good versus when it can be harmful • The mental activation that comes with gamification and identifying what behavior is being rewarded  • Hiring an advisor who won’t bleed you dry and the three questions you should ask a financial advisor   • How to know if your advisor is actively doing the work to help you meet your goals and recognize your money values • Why you want an advisor who works with people similar to you •  Paying attention to professional designations and understanding the regulations and standards that come with them • Why a CFP (Certified Financial Planner) is the gold standard of financial advisors • Understanding what an advisor does for his/her clients • Who the perfect Stacked reader is • Emily’s retirement readiness checklist and the things you should be thinking about to be ready to retire • Identifying one good thing everyday    No Stacking Benjamins hosts were harmed in the making of this episode.  Visit dontretiregraduate.com for a full transcript of this episode. Download Emily's Retirement Readiness Checklist at emilyguybirken.com/DRG About Emily Guy Birken Emily Guy Birken is a former educator, lifelong money nerd, and a Plutus Award-winning freelance writer who specializes in the scientific research behind irrational money behaviors. Her background in education allows her to make complex financial topics relatable and easily understood by the layperson.   She is the author of several books, including The 5 Years Before You Retire, End Financial Stress Now, and the brand new book Stacked: Your Super Serious Guide to Modern Money Management, written with Joe Saul-Sehy.    Emily lives in Milwaukee with her family.  www.emilyguybirken.com Facebook: Emily Guy Birken Twitter: @EmilyGuyBirken Instagram: @EmilyGuyBirken  LinkedIn: Emily Guy Birken Learn more about your ad choices. Visit megaphone.fm/adchoices

In today’s Office Hours, Eric answers Felix's question: what is the most valuable employee benefit I should take advantage of? This is a great question and the answer varies by person, but there are a few employee benefit options that most people underutilize and even ignore. Find a full transcript of this episode at dontretiregraduate.com. Have a question? Tweet it to us at @BrotmanPlanning or post it on our Facebook and it may be used in a future episode of Office Hours! Learn more about your ad choices. Visit megaphone.fm/adchoices