Entrepreneurship Is Hard. Here’s What Keeps Me Grounded.
Jun 03, 2025
This is a bit of a different kind of post — not the usual nuts-and-bolts business tips. Instead, I’m talking about something that doesn’t get enough airtime: the emotional side of entrepreneurship.
A few key points I hit:
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Entrepreneurship is hard. It’s rewarding, sure — but it’s also harder than most traditional jobs. You need real emotional resilience to weather the ups and downs.
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Burnout is real. Hustle culture glorifies working yourself into the ground, but that approach has diminishing returns. You can’t show up well for your business (or your life) if you’re running on fumes.
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A few things that help:
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Meditation. This is one of the highest ROI practices I know — even 15–30 mins a day can make a big difference.
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A support network. You need people you can talk to — entrepreneurship can be lonely.
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Professional support. Coaches, therapists, mentors, peer groups (EO, YPO, etc.) can help you stay grounded.
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I also share a bit about my own practices — the mix of coaching, therapy, and meditation that helps me stay steady.
This is the first in what I hope will be a series on the “soft skills” of entrepreneurship — things like money, partnerships, relationships, and more. Stay tuned.
Transcript:
 All right, so doing a little something different here in the blog today, we are going for a slightly longer form, hopefully not too rambling or meandering audio cast here. And today I wanna talk about something a little different. It it's starting luck. We often talk about all these like tips and tricks to start a business and to start scrappy and to get something built and to how to test it and how to.
Learn more about your user and your potential customer. We talk about like very brass tacks things, which is what we want to talk about. We wanna give people the bare knuckle information to get started and to get going and to make some things. And, and that's our primary goal and that's what we heard from people that they want was to know exactly what to do.
And, but today I wanna talk about something a little bit different, and that is like the emotional side of starting a business and being an entrepreneur. First off, I'd say that business, like starting a business, opening your own business, developing products and services, being your own boss, all those things, it's, it's very hard.
It's hard work, incredibly rewarding. And I wouldn't do it any other way, but it is technically harder I think, than having a JOB, than having some place where you go to every day and you just show up and they tell you what to do and you just do it right. So it's a very different thing, but there's this emotional component that is certainly worth paying attention to.
And I think resilience, that that word has really been very prevalent over the last, I don't know, couple of years. You talk about resilient leadership and we talk about resilience in entrepreneurs and the ability to. Endure the hard times, the ability to stick with it when it feels like our clients or customers are not buying our products or services anymore.
The ability to work through hard relationships with customers or with contractors or with employees, these things can be really tough and they're a little bit different than the way that they operate inside of an organization as an employee. And so there's a couple things that I would wanna say. One is that it's really easy to end up wanting to spend all of your time.
Trying to figure these things out and try to solve for this. And it can be very frustrating. And there's a, there's definitely a point of diminishing returns, right? If we spend 10 hours a day or 12 hours a day trying to figure something out or work on something and, but we're not taking great care of our emotional selves, our maybe our body, our physical selves, kind of everything else, and even our brain, right?
Taking care of our brain, we will hit a point of diminishing returns. Now you get a lot of that kind of hustle porn. Grind core stuff out there that's just work your ass off, work 24 hours a day and never sleep that stuff. And I hopefully that's even been made fun of enough now where it's going away.
Like most of us started our own businesses because we wanted to be in charge of our own destiny. We wanted to be in charge of our life and the hours that we work and the hours that we don't work. And we wanna be able to take our kids to little league and pick 'em up at school and be available for those other life things.
And in order to do that, we have to level up our resilience skills. We have to level up our emotional intelligence in ways that you're just not forced to inside an organization. So this is a series that I want to talk a little bit more about and I want the rest of the team to chime in here too. 'cause we all have, you know, decades of experience of being entrepreneurs, of running our own businesses.
And so I think everybody's gonna be a little bit different. But I'll share a couple of things that I think help really keep me on track. From an emotional standpoint as an entrepreneur and as somebody who's really trying to like balance, like I really want a really great work life balance. I don't wanna work too much, even though I love working.
I wanna spend a lot of time with my wife and my dog and, and so there's a couple of things that I think are super important. One you hear me talk about all the time, meditation practice. I could talk about this for days. It's the ROI is so huge on sitting for 15, 20, 30 minutes a day in meditation. Get an app, get a teacher, whatever.
Watch some YouTube videos. There's a lot of ways you can do it or you can do tm. There's tons, but find the thing that works for you. Be deliberate. Be a seeker and find the thing that works for you, and then commit to it and watch. It'll start to pay off. You will not feel great day one, day two, day 10, but over time, meditation will pay big dividends as an entrepreneur.
There's a million gillion entrepreneurs out there that don't meditate. I'm not one of them. The next thing I would say is workout. Make sure that you are moving your body a lot. Most of us, most of you probably listening to this, are sitting on laptops and phones most of the day. And so as much as you can get out, move your body and at least at the very least, be walking 30 minutes a day.
If not, get into a gym or get on the bike or go swim or do any of those other things. All right, so those are the two big things you hear me talk about all the time that I think are, have been so important for me. A couple of other things that I would say use a calendar. When I talk to clients that are entrepreneurs that pretty much all of 'em use a calendar and know how to use a calendar.
But when I talk to unorganized people, unmotivated people, they never have a calendar. They never know what they have coming up the next day. They're really bad at scheduling stuff, and so they can't commit to anything. They can't be, they don't know their availability, and so they also can't measure how much free time they're getting.
Their meditation's not in the calendar. Their workouts are not in the calendar, so. Get a calendar, use it, stick to it. Don't pay for some shit, just use Google Calendar or Apple Calendar or whatever. And then the last thing I would say is find support. Find some support. Most of the time it's not our contractors, it's not our customers, it's not our employees.
And a lot of the times it's not our significant others either. Like my wife does not really want to hear about me talking about work for more than about 10 or 15 minutes at a time. So I have to find other places, other people. To share these things with, and then I also offer that for other entrepreneurs, right?
But get a coach, get a therapist, get a mentor, find a peer group. Join EO or YPO. You can join my coaching group. Or just a buddy. Maybe you've got a couple of buddies that are entrepreneurs and you guys can share tips and tricks and get some support and that peer way that can be so super helpful. Again, all of these things are for emotional resilience, endurance, stamina.
Stability and so big believer in all of these things. If you're gonna be an entrepreneur, you're choosing the harder route. But I'd almost venture to say that you're choosing a better route. That's not true for everybody, but it's true for those of us that, that like being an entrepreneur. For those of us that like wanna do our own thing, it's the harder route.
Find some good support, find ways to keep yourself in line. Keep the train on the tracks. Personally, I have a coach. Uh, I oftentimes have a therapist. Sometimes I don't, whether it be one-on-one. Sometimes we have a couple's therapist. I have a Dharma teacher that I, you know, sit with and do meditation with and go on meditation retreats with.
I have a lot of people in my life that keep this train on the tracks, right? And, and it pays big. So I'm a pretty happy guy. I wake up feeling pretty good most days, you know what I'm saying? I don't wake up, freak out. I don't wake up nervous, worried. I don't think about bad conversations that have happened.
I get to live pretty damn free. I think mostly as a result of having these things in my life, having these practices in my life. All right, that's it. That's the first one of these episodes where we're gonna talk a little bit more about the emotional side, the soft skills of being an entrepreneur and how we deal with the ups and downs and the ins and outs of running your own business.
That'll get into areas of like money and partnership and relationships and all kinds of cool stuff, but I'll share more about this in the future. I also hope that. My team's gonna jump in here. Jacob and Amy and Jesse and Daniel and the whole gang. Really looking forward to it. And if you have thoughts, man, we sure would love it.
Pop in, tell us what you wanna hear about, tell us what you wanna know about if you are a new entrepreneur or an aspiring entrepreneur, we certainly want to hear the questions that you have, the concerns that you have, the wins that you wanna celebrate, all that shit. We're wide open for it. Let us know what you got and we look forward to catching up with you soon.
Thanks y'all. Talk to you soon.
Starting a business can feel incredibly overwhelming and confusing.
That’s where we come in. Just a couple of punk rock, do-it-yourself guys who have started a few businesses, learned a lot along the way, and have a good strategy to help you build a small, sustainable business that can generate  profit and set you on the path to freedom from being an employee for the rest of your life.