In today’s episode of The Startup Chat, Steli and Hiten talk about doing what scares you.

When trying to accomplish something, the fear of the unknown can prevent you from taking action and completing your goals. Whatever it is that scares you, overcoming that fear and completing your goal can only be beneficial to you.

In this episode, Steli and Hiten talk about how doing things that scare you can help you grow, situations where being scared can be a good thing, some business situations that scared them in the past and much more.

Time Stamped Show Notes:

00:00 About the topic of today’s episode

00:27 Why this topic was chosen.

01:50 How doing things that scare you can help you grow.

02:01 How doing something that you’re scared usually leads to something valuable.

03:06 Situations where being scared can be a good thing.

04:02 How listing out things that scare you can be beneficial.

05:23 Why you should feed the fear in a positive way.

06:39 How everyone, including founders, has something that scares them.

07:21 How a lot of founders are driven by fear.

09:09 Business situations that scared Steli and Hiten.

3 Key Points:

We grow by doing things that we’re not comfortable with.
There’s something valuable at the end of fear.
I would like to see more people list out the things that scare them.

[0:00:01]

Steli Efti: Hey everybody, this is Steli Efti.

[0:00:03]

Hiten Shah: And this is Hiten Shah and today on The Startup Chat we’re going to talk about doing what scares you. The reason I want to talk about this is because recently my FYI co-founder Marie decided to go on a camping trip alone, but not quite alone because she was with her dog, which is probably even more scary in some ways. And in a bunch of private chats she was talking about bears and being scared of bears, and we’re in California and apparently there’s bears. And then on Twitter she was talking about how she was doing it. And what was really cool is a lot of other people chimed in about going on solo camping trips and dealing with the fears and things like that, making a fire and all that good stuff. So yeah, just wanted to talk about doing what scares you because it can extend to anything, personal life or work or whatever. Really just, I think something that we tend to sort of as humans, we grow by doing things that we’re not comfortable with, doing things that might scare us. And at the same time we also kind of don’t do them. So we lose out on growth and on opportunities like that. And personally I think there are things that I’m thinking through right now myself that probably scare me a little bit and but yet I know that they’re going to help me grow. And I know that I want that and I want that experience. So yeah, just wanted to chat with you about this because I think it’s a very common thing and something that a lot of people can get a bunch of value from.

[0:01:41]

Steli Efti: I love it. So I think that, I’ve said this many, many times that I do think that fear is the compass, fear points usually to a direction … There’s something valuable at the end of fear. There’s something, either it’s outside your comfort or … It’s always outside of your comfort if it’s associated with fear, I guess. But doing something that you’re afraid of usually will lead to something valuable, a valuable experience, a valuable skill or quite a valuable thing that you accomplish. But because there’s fear in between you and that thing or that experience, it’s what’s holding most of us back. But I wonder, I recently wondered if that’s always good advice. First, maybe and this is funky, I don’t know if this is going to lead to any place worthwhile going or exploring, but are there exceptions to this? When is it right to let your fear hold you back or to let what scares you define what you do or you don’t do? Are there situations where fear is … I mean, of course life and death. Don’t maybe jump into the lion’s den, whatever. The zoo, maybe don’t go near or into areas of wild animals. Like there’s survival situations where fear is probably a good instinct to follow or to listen to. But in more day-to-day life, in more life decisions than aren’t life and death, is there ever a place where we need to listen to our fear or where what scares us is something we should not move towards to?

[0:03:28]

Hiten Shah: Yeah, I mean I think if something scares you and there’s some level of life and death associated with it, around whether you do it you might die. Like in die without appropriate measures, so it’s really risky. So I think one of the things that comes into play when it comes to doing what scares you, it has a lot to do with risk and how risky is it. Is it a life or death situation, things like that. Those are one kind of aspect. I think another one is when it comes to what scares you, if I were to be very prescriptive, I would love to see more people do an exercise of actually listing out the things that scare them. Whether it’s something they’re about to do or something that in general would scare them. Like my girlfriend, [Anna-Marie 00:04:20], she’d probably list down going camping alone would scare her. She also has probably a lot of things that might scare her besides that as well. Not to blow up her spot, but like, yeah. And in my case, I think a lot of things that scare me … Like going camping alone to me is not even scary because I just wouldn’t do it. It’s not a desire.

[0:04:43]

Steli Efti: Yeah.

[0:04:43]

Hiten Shah: So there’s this whole idea of do you desire it? Does it scare you, what parts of it scare you? Because you don’t desire it and it’s something scary for you, you’re not going to do it, it doesn’t matter. There are a lot of things that I don’t desire so I don’t even think about them. Well in her case, she desires that, she’s gone camping with other people before. She went camping when she was a kid. So this is a big … It was probably I think actually a big milestone. I’ve seen her after that and I think that was a big milestone. There’s possibly even something that’s changed in her as a result of this experience, frankly speaking. And so a part of me is like when you think through things that scare you, things that you desire that scare you, or things you gravitate towards but they still scare you. It’s almost like you want to feed the fear in a positive way. And yeah, I’m sure there are things that scare you that you shouldn’t do. Like go, I don’t know, go hang out with a snake, a poisonous snake. Maybe you shouldn’t do that. So yeah, I find it a fascinating topic because the things that scare people are very different. Like there’s things in business that scare me and I definitely do them. And there are things in business that probably scare other people that would never scare me, whether it’s because I’ve done them before or I am just comfortable. Like just general most business stuff. I think another way to think about it that I know some people would throw back and be like, “Oh, nothing scares me.” I would say that then you probably might not be able to really grok and understand the definition of the word. Because as a founder or as somebody who’s sort of done a lot of things in their lives or is trying something new like starting a company or something like that, you might already have this idea in your head where founders have no fear.

[0:06:36]

Steli Efti: Yeah.

[0:06:37]

Hiten Shah: I don’t know how true that is. I don’t believe that.

[0:06:39]

Steli Efti: It’s total bullshit.

[0:06:41]

Hiten Shah: There you go.

[0:06:41]

Steli Efti: That is absolute and total bullshit. I think in general a lot of the things that we say about founders is bullshit. A lot of self-beliefs, anything that really makes, that distinct a group and makes it better in some way from other groups, in most cases it’s probably has a lot of BS in there. I think that founders are just as scared as other people are. They’re just scared about different things. You could appear to be incredibly brave because you do all these crazy things, but what really drives you is fear, and the fear of being insignificant maybe. The panic and fear not being admired and loved might push you to do these crazy stunts that are physically very dangerous because you’re not afraid to die or not afraid to get injured, but you’re really afraid to be alone or being insignificant or whatever. And you don’t know what drives people, and a lot of founders are driven by fear. They’re not just driven by whatever, they’re vision to change the world and by their bravado and … Yeah, that’s a cool story but I have met a ton of founders, I’ve been a founder almost my entire life, adult life. Very similar to your story. We’ve been exposed to a lot of founders and I wouldn’t be able to say that I’ve observed less fear in the founder or entrepreneur community even than in other communities. And let me ask you, you said that maybe something that will be useful to people listening to us is to share a … You shared you’re co-founder doing something. It’s kind of outside of the business world that was out of the startup world that was something she was scared of, which is dope. Like going camping alone or something she was afraid of, and I think I can totally relate to her feeling empowered by overcoming that fear and going, “Hey, I’m strong. I did it. I overcame my fear, I survived. I can be in slightly more dangerous situations that I’m used to and I can do well. And it’s fine.” Those are always awesome moments. But I’m wondering, maybe we should also share more recent moments where we were afraid or were scared of something, or wanted to do something we were scared of that relates to the startup world in one way or another. And I’ll go first. You can ponder what example you want to share and you can go second. But I always feel like when people like us that some people might admire and look up to, when we go deep and share something that’s current, it makes it much more alive than when we just talk about the topic.

[0:09:31]

Hiten Shah: Yeah, so far [inaudible 00:09:34].

[0:09:34]

Steli Efti: So now I’m thinking like, “What the fuck am I going to say?”

[0:09:37]

Hiten Shah: I know.

[0:09:37]

Steli Efti: This is part of why this podcast is so popular and a lot of people get a lot from it, is that it’s not scripted. We don’t really spend a lot of time thinking through what we’re going to say. I did a bunch of podcast recordings in the last three weeks because I want to promote the new book that we brought out at Close and all that. Most times when I do a podcast recording I’m like, “Wow, all these people do this completely differently from how we are doing it.”

[0:10:04]

Hiten Shah: That’s right. That’s right.

[0:10:06]

Steli Efti: We don’t do second takes. We don’t have a script. So, okay. So something that I recently did in business that that scared me. So the biggest thing that I can think of is actually the … Well there’s two things. One, we did a very big pricing project, it closed at the beginning of the year. I think I’ve talked about this on the podcast before for sure. That was against kind of one of the beliefs that I have for a very long time and I was scared to change things. I always loved simple pricing models and I always loved that we offer people three simple pricing tiers and you could have all you wanted. And one of them is kind of like … Especially the telephony piece that we do, that we allow people to make calls and receive calls, send text messages and all that. I always hated the idea of having a usage-based pricing. I always wanted to give people a package because that to me was simple, that’s how I want to buy things. So I always resisted that and then eventually I convinced myself that I was wrong and that we needed to switch our pricing model. And when we started working on that pricing project and changing completely how our pricing infrastructure works, I had a a couple of moments where I looked at the math and I said, “If this doesn’t work out, it might really get get us in big trouble.” And it was interesting to see how I got scared a few times, just that that emotion came up. I was surprised about it myself and I was like, “Wow, I haven’t felt this in a while.” But last times I placed really big bets, I placed bets where the team was much smaller, the business was much smaller. And it seemed like if those bets didn’t work out, nothing really bad would happen. But now it’s a much bigger team. There’s a lot of people here that pay their mortgages, have children, have their families, I’m responsible for a lot of people. And this business is quite big. And so making this big of a bet, making this radical of a change for us and having the worst case scenario would be one where we lose a ton of revenue, that was quite scary. And I was both surprised by that. I had these moments literally hit me where I would go, “Shit, I haven’t felt this in years. This is a weird feeling. What do I do with this?”

[0:12:31]

Hiten Shah: That’s pretty awesome.

[0:12:32]

Steli Efti: It’s like, “Ah, I haven’t felt scared. This is so weird.” And then I had moments where I went back to this I think deep belief that you and I shared that’s like, “Well, if I’m scared at least we’re doing some real shit here.” We’re changing something, we’re really … “And does my rationale makes sense, why are we making this decision?” I would go through the rationale again to make sure that we thought this out carefully through and I still believe it’s the right decision. And then it was just about embracing that fear and thinking about it, reframing it as excitement and going, “You know what, maybe I’m just going to think about this feeling as excitement. Maybe I’m just excited about this. Maybe something real is happening.” So that’s one example.

[0:13:11]

Hiten Shah: I like that.

[0:13:13]

Steli Efti: I thought of another quick example in there, because it feels closer, the kind of more intimate. This is, I don’t even know if it fits in terms of doing what scares you. Well, in some ways it does, but I think what I recognized this year is that for the past 20 years of hiring people, employing people, I’ve learned to deal with conflict and I’ve always been very frank with people. But the underlying working principle that I have when it comes to people is that I am a seeker of harmony. This is hard to believe for some people that know me, but I do like harmony and I want people to be happy and I want things to be aligned, and everybody to be in a good place. I’m not necessarily somebody that enjoys conflict. And a tax conflict was like a passion, an excitement. Like I try to avoid conflict or I try to eliminate conflict whenever I can. That’s kind of my operating principle. And I remember a couple of months ago, two or three months ago, there was a situation with somebody on our team where I had to have a conversation with this person about something that was quite a difficult topic to discuss. And there were very high chances that it wouldn’t go down well, I it would create kind of a bad situation between the two of us. And I remember that back in the day I would have gone pregnant with that task for awhile, I would have thought about it a lot. I would have constantly tried to optimize for the conversation on like, “How can I have this conversation to make sure it doesn’t lead to conflict? How can I break this news and talk about this topic with this person in a way that’s going to make this feel as good as it can?” That was kind of the thing that guided my game plan in the past. And this time around for the first time, I kind of left that behind me and I was like, “Well, this is not a good way of thinking. Of course I don’t want to upset anybody, I don’t want to have an argument. But that can’t be my number one goal. My number one goal is X. So I need to optimize this conversation to accomplish X and I’m going to do it in a humane, fair and transparent way. But if the person gets upset that’s beyond my control and it’s going to pass.” Like I shouldn’t like overly optimized for that. And that was the first time that I went into a conversation where I didn’t care how the person would react. I was like, “I know this is the right thing to do. I know that I’m going to focus on the right way. And if this person gets upset, they get upset, we’ll deal with it then. I’m not going to spend all my energy and time on trying to cockup some way or some strategy that makes me feel safe, because I think I can get into this conversation and have a high chance of of talking about this in a way that will feel good to this person.” And I don’t know, that was a big shift for me and it changed the way I feel about the people I work with from a … I still deeply care about them, I want all of them to be happy and fulfilled. But I’m not as scared as I used to be to confront people or to have very difficult conversations earlier, and with a different focus than in the past where I think I oftentimes over optimized for harmony than anything else. So that was kind of a … It was a conversation where I didn’t have that fear anymore that I used to always have in those situations.

[0:16:25]

Hiten Shah: Yeah, I can relate. I think one that I’ll share that’s quite similar and a little bit different is I always had the fear of somebody not liking me. And in business I think it can be really a harmful thing when you have that fear and you have to make good business decisions, I mean great business decisions. Because if you’re fearful of somebody not liking you, then you might not do the right thing. You actually probably won’t do the right thing. I’d even go further and say that.

[0:17:01]

Steli Efti: Yeah.

[0:17:01]

Hiten Shah: And all I’m trying to do is I’m trying to do the right thing. And it’s really tough to do if I have this fear that they’re not going to like me. Because it’ll stop me from figuring out, it stops me from figuring out what is the right thing to do, and how can I do that right thing in this moment regardless, and the right thing for the business. The right thing for the people on the team, not necessarily driven by what I think is the right thing that’s going to keep my psyche happy. Where it’s like, this person likes me or doesn’t like me. And the funny thing about this is I’ve just been aware now of this and that’s all I really needed to do. Once I became aware of this, everything I did got converted over to being more so about doing the right thing versus doing the thing that prevents people from not liking me. Because that’s also a very subjective thing. And more importantly, I don’t control whether someone likes me or not. Realistically, it’s not even my problem. I know that sounds weird, but whether someone likes me or not, I can just do the best I can. I should not be trying to optimize my life around somebody else liking me. And so I used to have, and probably there’s still parts of this that exists for me, but have this fear of that. It’s basically this fear that, “Oh, they’re not going to like me.” Or this fear that I’m going to say something or do something that’s good that I need to do,, but in that process, they’re not going to like me or they’re not going to like what I have to say. So I stopped worrying about that and it’s really been transformative for me. And this is almost like a daily fear of mine that I’ve had to work on, very similar to what you were saying where I kind of want to be liked. And I even overthink it, I overthink the message. I overthink saying something. I overthink how I’m going to say it with honestly the wrong attitude. And I think the wrong attitude is overthinking it with the idea that whatever I say they should like me. It’s actually more important that whatever I say, it should be true to what I want to communicate, and what I need to be saying in that moment in order to achieve whatever goal or outcome I’m looking to achieve. That’s now more important to me than saying things that someone else is going to feel okay about. Because I can’t even predict that in a lot of cases too. I can’t predict whether I’m going to say something and someone else’s going to be okay or not okay with it. And this doesn’t mean I’m not compassionate or I don’t try to be compassionate, I think all those things are important. But I should not be driven by this fear that someone else is not going to like what I have to say or what I’m doing.

[0:19:48]

Steli Efti: Fucking love it. All right, this is it from us. Do what scares you.

[0:19:53]

Hiten Shah: There you go.

[0:19:54]

Steli Efti: And what is scaring you? That might be a good question to end the episode with. If you feel like sharing, send us an email steli@close.com, hnshah@gmail.com. Let us know what scares you and what you’re going to do about it, and we’ll hear you very, very soon.

[0:20:13]

Hiten Shah: later.

[0:20:13]

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