A lot of you that have taken the plunge or are thinking about taking the plunge into entrepreneurial endeavors. If you have dabbled with it you probably have already experienced the emotional roller coaster that is part of the entrepreneurial journey.

  • The stress
  • The fear
  • The complete curve balls life will inevitably throw at you
  • The pain from all of the little failures that must be endured to eventually get to success.

All of this builds up and can be emotionally draining. So much so it can drive you into a depression if you are not careful.

I admit I am not immune from this depression. This time of year is especially difficult for me if I am not careful. Summer is over, I just got back from camp. I am no longer nearly as physically active, nor am I constantly surrounded by the smiling faces of my athletes and the other camp staff. I go through a sort of withdraw from the summer time high(No I am not on drugs).

On top of all of that I have one of the largest proposals of my career on the line that could change the next decade or two of my life. As I eagerly wait for the potential client to make a decision my mind can drift to dark places. Imagine how holding your breath waiting for that big email or that phone call feels. It is intense. And if they don't bite then all of my work so far on the proposal has been in vain. Questions start creeping in like:

  • Is there something more I can be doing to push the deal forward?
  • Should I take a smaller deal that comes along instead of holding out for the grand slam?
  • The clock is ticking, our runway is running out. How much longer can I wait?

All of this can lead you to a dark place. If you find yourself thinking dark thoughts do not fret: You are not alone.

Lots of great leaders and entrepreneurs have had to deal with it in various degrees. Perhaps you have heard of Abe Lincoln's bouts with depression. One of my favorite authors Tim Ferris has written extensively on the topic.

Don't feel bad that you find yourself in a dark place, that just adds fuel to the fire. Instead here are some of the tactics I use to counter depression and stay productive.

Stay physically active:

One of the best things I did was to adopt a morning workout routine. I might have 60 hours worth of client work to do or I might have none.

Without the morning workout routine if I was busy I might have been tempted to start working right away and let my personal health go to hell. On a long enough time line that would be a really poor investment.

If I didn't have any projects I might be tempted to sleep in because I did not have any obligations that day but if I slept in then I am not working towards finding that next project.

Fortunately because I had my morning training to wake up for I would get up, hit the gym, and be wide awake and ready to work or at least hit the pavement looking for work.

Weather you are buried in work or completely lacking paid work it is no time to sacrifice your health. Get active, it is an investment that pays off in the near and distant future.

Get outside:

Winters in Wisconsin can suck. The complete lack of sunlight combined with confinement to indoors can quickly cause your body to go into hibernation mode. This physical depression combined with the additional stresses can be a powerful force dragging you down.

If you have an opportunity to get out and get some sun take it. At TownSqua.re one of our traditions was to take a lap or two around the capital building. At camp I am constantly coaching in a giant open air gym with a beautiful view of the mountains and plenty of fresh air.

Instead of eating lunch or dinner indoors take a walk and appreciate nature. If you have a meeting that can be done sitting under the shade of a tree then take it there. It will make a difference in your day.

Be around people:

I can't stress this one enough. Being in tech and with the ability to work remote can accidentally cause you to be isolated. Often times when I was younger I locked myself away in a room to work on whatever idea I had without distraction. Soon my productivity would drop and I would start to feel down. After 3 solid days of staring at a screen I would realize I haven't seen or spoken to another person in as long.

Get out there and mingle. These days I have several safeguards against this:


A co-working space a bunch of us had a hand in starting here in Madison. It is full of battle hardened entrepreneurs as well as fresh faced dreamers just starting out their journey. I can go in there almost anytime and find someone with an interesting project or problem to take my mind off my woes.


Teaching is a very powerful thing. The ability to help another gives us a sense of value during those dark times when we might feel worthless. At almost every major setback in business and in life I find myself retreating to the gym to coach and get my head on straight.

There is also something about working with kids. It keeps you humble and it keeps you young at heart. I am somewhat convinced that coaching is a type of fountain of youth.


My family is the final safeguard. I am so fortunate to have such an amazing family to fall back on when things are tough. I encourage you to make your family part of the your journey as much as possible.

Sharpen The Axe:

So there is no paid work coming in. Maybe it is time for you to further improve your skill set, your tools, or your business processes. The open source tools I build during my down times have elevated me to a whole new level. NJax, a framework for rapidly deploying Micro Service Architecture is a tool I have been working on that has evolved over the last 6 years. It allows me to build things in hours that might take others without such refined tools months to build.

My trilaterting WiFi and Bluetooth signals project I started when I was dieing of boredom between projects went on to land me my largest deal to date.
(Cross your figures but hopefully my Genetic Learning Neural Network AI Project "Chaos Engine" might do the same soon)

Weather you have unintended downtime or your burnt out and need some revitalization take some time to sharpen your skills or work on a passion project.

Be grateful:

The final thing I try to do is be grateful. This might sound like some new age mumbo-jumbo but I find it helps me put things in perspective. Maybe you find yourself thinking "This project is going to be the death of me". What if it does kill me? Then on my deathbed what experiences have I had that I will look back on and smile?

  • Every new skill stuck by an athlete I coached
  • Every dinner and phone call with my family
  • Every joke and subsequent good laugh with my friends
  • Every time I learned a new skill in the gym
  • Every drawing in my sketchbook
  • Every first kiss(and all to follow) with any girl that has been so kind as to suffer my company

And a million more things that would take to long to list right now. Just writing the above list makes me feel better. If you are feeling down right now just take a couple of minutes and go over all of the things that you are grateful for; past, present, and future.

You might even want to try writing them down and putting them on your desk to keep things in perspective when all goes to hell.


I know this post started out about dealing with the entrepreneurial emotional roller coaster but in reality all walks of life have their ups and downs. Whatever the cause when you find yourself in a dark place I sincerely hope with all my heart that these tips can help guide you back to a brighter place.


Business , Life

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