in life

The Momentary Breakdown (and Breakthrough) of a Successful Entrepreneur

Every so often, I have a break down. Stress gets to me. I feel overwhelmed. Like I can’t breathe. That everything I’m doing is too much. I look at the path I’m walking and I conclude, temporarily, that I must have been kidding myself when I thought I could run my own business. I let doubt creep in, and then consume myself with it.

I worry. I worry too much. Even though I’ve been at this for nearly three years, I always wonder if the next client will come, or if I’ll be able to deposit the next paycheck. They keep coming, and I keep getting paid, but I still worry.

You see, I’ve tasted success. Success beyond what I ever expected of myself at this age. Maybe ever. And I never want to let that go. I never want to take my finger off the pulse of what I’ve created. The life I’ve helped to create for my wife and I.

As Jill Felska said in this very poignant post a few months back:

“…The thing is, we don’t stop. We continue to go and go and go. To us, I think the only thing scarier than not succeeding is the thought that all the work we’ve done to get ourselves here would go to waste…”

So I push hard. Then I push harder. I take on new challenges. I decide, on a whim, that I think it’s time to train for a marathon. Yet another responsibility to add to my already full plate. It’s this little game I play with myself called, “How much can I take on before I explode?” – So far, no explosion, so I can keep taking things on, right?

And yet I still believe it’s going to get better. My wife asks me every couple weeks, “When is it going to get easier?” to which I respond, half-heartedly, “Soon”. Because you have to work more to work less, right?

What you hear about entrepreneurship is how amazing it is. How intoxicating the freedom of answering to only yourself can be. How incredibly rewarding it feels to take ownership of your accomplishments.

Hell yes. It’s all of those things, and then some. But what you don’t hear is about the constant stress and pressure of having to be “always on”. What it’s like to forget what a a “real” weekend is like. That with accomplishments, comes failures, angry clients, missed deadlines, proposals denied. All of which fall directly to you. It can be a tough pill to swallow.

Entrepreneurship puts you in the drivers seat. It gives you great power. But with that power, comes great responsibility. Responsibility you’re not going to be ready for, until you’re faced with it. Until you have to be. Until you’re forced into making a bold decision, in the moment, that’s going to feel impossible to make.

Don’t let the aspirational words of wisdom and motivational “you can do it” mantras of bloggers and self-help gurus fool you. As much as you can, you can’t. And you shouldn’t. If you’re forever trying to keep up with someone else, you’ll realize that you’re never, ever going to be satisfied.

I read this post by my friend Nicole yesterday, in which she describes her breakdown after the realization that she couldn’t afford her son’s medicine It wasn’t so much the story, but her final conclusion, that resonated with me:

“…I realize that we are all fighting a battle in one way or another. Whether we have no money, or too much money, or too much pain – we are all battling our own version of the system – large and small…”

We all struggle. In different ways, shapes, and forms. This shit is hard. The whole, life thing. Whether you’re running your own business, working in an office, or unemployed. We’re all struggling. But we’re all succeeding. 

Nicole faced first-hand how much of a bitch our healthcare system can be, but no doubt realized and realizes how amazing it is to have a beautiful little guy in her life to take care of and call her son.

Jill had a breakdown a few months ago, but after a few tears and some dark chocolate, realized that she felt stronger and more empowered than ever before.

This weekend I wrote a $20,000 check to the IRS. My “tax return”, if you will. It felt like someone shot me in the stomach, kicked me in the nuts, then shot me in the stomach again. I was legitimately depressed. But then I put some things in perspective. Last year my wife and I traveled to new places, we bought a house, my company grew exponentially, I’m healthier than I’ve ever been, and life is good.

I surmized that it wasn’t always easy and it’s never going to be. But it was and always is totally worth it. I didn’t say goodbye to half my life savings, I said hello to a clean slate of building on the success of last year and making this year that much better.

Which just goes to show that in the midst of our breakdowns, comes breakthrough…

(Photo credit)

Add Your Voice



  1. I don’t want to pay taxes. That last part about writing a check for $20,000…it was enough to convince me that I don’t want to pay taxes anymore. (JK, but seriously). And yes…sometimes a few tears and a bar of high quality dark chocolate is all it takes to put things back into perspective. I’m a big fan of that remedy. 

    • It wasn’t until the past couple years of paying a stupid amount back in taxes that I started to understand why so many people get in trouble for evading taxes. Reporting quarterly from now on will help, but if there’s one thing that stinks about running your own business, it’s taxes. And sadly, it’ll never get any better…Comes with the territory I suppose. But yes, dark chocolate helps. :)

      • taxes is the one thing that scares me about business and actually keeps me from doing it.. (talk about letting fear control..sigh). i would probably evade taxes out of pure stupidity and naivety/ignorance. when i get to that point, i’ll definitely hire my own accountant though.

        • That’s my best piece of advice. Get an accountant to do it for you. Paying taxes will always suck, but it sucks less when you don’t have to worry about filing yourself…

  2. I’ve always loved your honesty Matt. You are so right, life in general is hard and I dont even want to think about taxes. I’m happy that you had $20,000 to pay it!! I learned last month that my employer is closing in June so Im being laid off, and to top it off, after processing my taxes I learned that I owe $1900 to IRS and $500 to state. It sucks when you dont get paid enough to live comfortably and not enough to pay taxes, then toss in the layoff. I woud have liked to save up something before I jumped into the world of full-time entrepreneurship, but ya know, it is what it is. I admire your story and your journey and I always find myself going back and reading your past posts for inspiration. Keep your head up over there. You have A LOT to be proud of! Thanks for being so transparent.

    • My head is held high – a product of having these momentary breakdowns is they keep you coming back. More knowledgable. Braver. Stronger. With understanding. Life is all about the ups and downs, ebbs and flows. It’s those who understand and master the give and take that really get the most out of life. I’m glad to hear my words continue to inspire you, Patrice.

  3. Love the honesty of this post. It’s nice to hear someone recognize that entrepreneurship isn’t all sunshine & rainbows and ass-kicking. Also, like you said, we all have struggles, and we all have successes. Having a breakdown every once in a while, getting overwhelmed, is totally normal, and I’m glad you shared this experience. You’re doing awesome things. 

    • Thanks, Sam. I appreciate the kind words. I guarantee you all the ass-kickers out there have their moments of weakness just like the rest of us. While I think it’s important to maintain a positive outlook overall, sometimes it helps to show the “real” side of what we’re doing, instead of pretending it’s always sexy and glamorous.

  4. I have nothing poignant or inspiring to add – you said it all – just going to say: I needed that. In a big way. Timely as always. Thank you, friend.

  5. Great post Matt.  I feel your pain.  I continue to believe I’m superman and cram more things on my plate.  Business, blog, running, family, travel…I think I can do more and do more “better”.  When it all builds up, I procrastinate, which always helps!  

  6. You’ve definitely said it all here – thank you for your honesty, Matt. I nodded my head throughout. This shit is hard. But breakthroughs are real and always worth it.

  7. Since I can’t leave much of a comment about this on Twitter, I’m graduating to the blog :) As someone who isn’t an entrepreneur (yet, working on it) but has always wanted to be one, I found this post so bold and inspiring. I’ll be 26 at the end of this year, and I could only dream of being at the point you’re at by that time. It’s so awesome to see someone so close to me in age that’s doing awesome things. I truly admire you and what you’re doing with your life. And, I think it’s so great that you’re willing to share the ups and the downs of entrepreneurship and why it’s all worth it. It reminds me what I’m working toward, even if it’s hard and not all sunshine and ponies every day (and I’m not even to the hard part yet!). Thank you, as usual, for always posting such great things at the right time!

    • My pleasure, Janelle. And I hope that through the ups and downs I share here that one message resonates loudest, and that is that everything I’m doing is totally worth it – and I wouldn’t have my life or career any other way. It’s not always easy, but I couldn’t ask for more right now, in this moment. If there’s anything I can do as you pursue your own entrepreneurial path, don’t hesitate to reach out.

  8. Sometimes it’s important to take a break. If we work til we drop then there is no point. I think its about finding the sweet spot between sweat and inspiration. thanks so much for your honesty. it sounds callous but sometimes its nice to hear others find things hard too otherwise you end up thinking that there’s something wrong with you! what you’re doing is definitely worth It and by the looks of these comments id say if you ever did need support you’d have it. Thank you for sharing :-)

    • Yes. If you’re constantly working on living at the sake of living, you’re missing out on what really matters. Unfortunately you DO have to work to live the life you want, which is where it gets impossibly complicated at times, but the whole “living” thing is where it’s at. The moments, milestones, and everything in between. I without a doubt appreciate so much the community I’ve built here on the blog over the past several years – it’s helped me get through some pretty crazy times, that’s for sure! Cheers!

  9. Love reading your blog Matt. With your success, your expected to share a part of it I guess. Now if you were inadvertently paying for your health insurance that way it might seem like a fair trade for a loved ones medicine, no? Up here I’m at peace with taxes. That’s my public health cheer! So happy to hear of you and Lierens success! Cheers to more future successes and your upcoming marathon!

    • Thanks, Sarah! Hope you guys are doing great up in the Northland as well! Hoping one of these days we’ll be reunited at a music festival equally awesome to Sasquatch ’11. Cheers!

  10. Thank you. It is somehow comforting to know we are all in this together.
    My breakdown regards facing retirement in the next year or so. On the one hand I welcome it as it will free up time for my writing but with it comes the the brutal realization,  that financially, this is it. What I see is what I get.
     Add this to the fact that I need a new car and soon – like this weekend! So, reduced income plus an added monthly expense Uh-oh. Maybe I’m going to have to put off retiring. We’ll see, 

    • Yes, it’s very much true that regardless of background, age, or current situation, we are all in this together – all struggling and succeeding. It’s easy to think there’s no light at the end of the tunnel, but there always is. Cheers, Virginia!

  11. Matt, thank you for your honesty!  As someone who is fairly new to running a business, thoughts like “What the hell was I thinking?” and “Really??? In this economy?”, etc. enter my head quite a bit.  It is so helpful to know that I am not the only one having occasional breakdowns.  
    Being a positive person overall, it is important to remember to be proud of all the accomplishments, all the strength of character it takes to be a business owner and continue to push through (yes, with dark chocolate and some wine, at times :)).  During those down moments it is also very therapeutic for me to focus on what I DO have in my life that a lot of people simply do not.  Most importantly, it is awesome to have love and support of my family and friends and be grateful that everybody is well.Katya Mathes

    • Yes. It’s all about putting things into perspective, isn’t it? That can be easier said than done, when you’re so caught up in your own little world, but being able to take a step back to truly see what you’ve done, what you’re doing, and where you’re headed, is SO important. Best of luck as you continue down the path of running your own business!

  12. Funny, I remember thinking as a kid that “older people” had their act together and their jigsaw puzzle pieces fit where they should.  Now, in my 50’s, I realize how mistaken I was.  Sometimes the pieces just “don’t fit.”  Too often, we then compound our action by taking it personally and discipline ourselves for the error(s), giving ourselves “Bad Me” messages because that has become conditioned in our lives.  Yes, yes; a mistake was made.  We have fallen into a hole.  Complaining and berating ourselves doesn’t get us out, though, does it?. The “breakthrough” comes in the acceptance and planning what to do next; the herd survives only when it keeps moving.
    I hope I’m not sounding preachy.  I’ve had some struggles, too.  This is a great blog, Matt.  Thank you for reminding us that we’re all human.  :)

    • Not preachy at all, Jeff. Just goes to show that folks from all walks of life, at any age, are dealing with their own struggles and successes. We’re all in this together – and we could all use a real and “human” voice like this more often…

  13. I haven’t even started my own business (yet) – although my wife has – but I’m feeling this. Feeling like I have no idea what I’m doing, or how I wandered into this path I’m going down, and while just a few weeks ago I couldn’t have been more convinced that I’m on the cusp of success, I feel as though I’ve just flat out hit a wall.

    Thanks for writing this. It’s helping me move through the mental paralysis just a bit better than I was before reading it.

    • My pleasure, Steve. The “hitting the wall” feeling doesn’t go away – but it gets easier to see the wall’s coming and to stay focused on breaking through them. Best of luck to you (and your wife).

  14. I SO know this feeling! I’m less than three months into full-time entrepreneurship and this week has had me on the brink as well. I’m so blessed to have a lot of work coming in, but there always seems to be more work to do than time to do it. It’s so easy to stretch yourself far beyond what you should. Striking a balance (at least for me) has been very hard. I know I haven’t taken a day off in a week or two…

    It’s funny – I thought that by quitting my job, life would be easier since I would only be working ONE job instead of TWO. But, now, I’m just working doubly hard on my business! I was seriously delusional to think that my schedule would ease up. You’re right – there are a lot of unicorns and rainbows all over the web re: being a business owner. Yes, entrepreneurship has so many benefits and I wouldn’t go back, but it’s downright tough. 

    I think the trick is that we have to tell ourselves it’s okay to stop and take a break. My husband (also a business owner) has mastered this. He’s really good at remembering that it’s just work and there is far more to life. And, he helps me with that too. It’s amazing how much better you feel once you pull back for a minute and give yourself room to breathe. I know that helps me.

    Hang in there!

    • Great points all around, Laura. And, I think the “taking a break” part comes easier as you fall into a rythym and, to put it bluntly, start believing in yourself. Once you’re not constantly worrying and doubting if you’ll bring in another client, you can focus simply on doing great work. Confidence is key, and it’s the only way you’ll allow yourself to let up and take a deep breath every once in a while.

  15. Wow, thank you so much for writing this post. This sums up exactly how I’ve been feeling as I prepare to launch my tiny PR firm. As the June 1st launch date draws nearer, I’ve been having more and more of these momentary breakdowns (“who do I think I am to expect that I can make this work?” is a thought that runs through my head WAY too many times each day) but then, I push through. And with each little breakdown comes a breakthrough of sorts, because I realize that as scary as this is, I still want it more than anything I’ve ever wanted in my life, and I’m going to make it work somehow. I can’t tell you how great it is to hear someone else express exactly what I’m feeling. 

    •  Alyssa have faith.  I launched mine on day 30 of my 30 day severance package and a year and a half later we are still rolling and starting to hire.  If a Forrest Gump like me can pull it off with no plan whatsoever you can kick butt with months to prepare!  Good luck!

    • My pleasure, Alyssa. What you’re going through right now is wildly exciting and completely terrifying. Keep looking toward the horizon. Focus on what you can do today, but don’t lose sight of the big goal(s) you have. Running your own business is hard as hell, but completely worth it. God speed as you’re about to take this big step in your life and career!

  16. A great post for me to read at this point of my career. 8 years working for myself and it’s both a struggle and extraordinary feeling every day. The doubt crept in for me last night and I was up late into the night just writing notes and trying to figure out the next steps. I hate those nights, but I guess they’re necessary to blaze your own path.

    I’ve really enjoyed your posts and your honesty- thanks for sharing Matt.

  17. Been a loooong while since I’ve been on here and glad I stopped by … Love the last statement … indeed, in the midst of breakdowns, comes breakthrough … but it’s the experiences we go through that make it all worth it. Resilience. The power to get beaten down and pull ourselves back up and try a bit harder, louder, bolder, stronger and then surprise ourselves by how much we can in fact endure. Entrepreneurship is hard. Being an entrepreneurs wife is harder! Believe me … the amount of times I’ve heard “things will ease up soon” … but they don’t, they just get more intense and more consuming, but I know and have faith that it will all pay off in the end, panic attacks and all. Hard work, persistence, perseverance pays off.

  18. As the inimitable Renzo Gracie of the legendary house of Gracie says: “Everyone is fighting something.” Sometimes we roll and it’s easy and sometimes it’s a shot to the stomach, a colostomy, and a kick to the nuts…