Entrepreneurs Depression: Overcoming My Own Self-Doubt

Before I quit my job and before I knew that all of the hard work would someday pay off I’d often have days and weeks of massive self-doubt.

These days I’ve learnt to overcome these thoughts – mainly through techniques like meditation and exercise and reading stoic philosophy. I’ll discuss a little later on here what methods and techniques I use to keep a clear mind.

Looking back though, I remember thinking “surely I’m not the only one who’s going through this”. I bet at least 80% of newbies just starting their entrepreneurial journeys have at some point felt the same way.

Entrepreneurs depression image

Anxiety, Depression and Massive Self-Doubt: The Things That Aren’t Spoken About

It’s a lonely road and most of the time a road where many of your dearest friends and family will sometimes tell you that you’re travelling down the wrong road altogether.

Many entrepreneurs seem to have something that you don’t have when comparing yourself to them. Most of my idols or mentors were either single or had a partner who is also an entrepreneur. I could think of only one who actually has kids and a wife–Pat Flynn. But his story sounds like something Disney thought up.

Often I was torn between a number of different thoughts which stem from a number of different goals and desires. A normal day would include thoughts on mostly my quest to have the freedom of working for myself and wondering if what I’m currently doing is actually getting me any closer to achieving that goal.

Also, my brain would throw around thoughts on health and fitness such as “I should be doing more to eat healthier” and “I should be exercising as my physique is beginning to resemble Mr Burns”.

(Actually, it still does… But I’ve just signed up at my local Crossfit box. 6-pack abs here I come!)

I remember most of the day while I was at my job and unfortunately a lot of time out of work I wasn’t just thinking about these things, but stressing about my 9 to 5 job as well.

Throw into the mix thoughts about being a good dad and husband and not to mention a whole lot of stress about money and how no matter how hard I worked, we always seemed to spend more money than we had, leaving us in a never ending debt cycle.

What worried me the most was my happiness or lack thereof.

I’d think “I’m chasing my dreams… why am I not happy about that?”

Some days I could deal with these thoughts just fine. On others I got so caught up in my head it was almost unbearable.

Matt Scott in hotel room working on laptop

Was I Depressed?

I don’t know. I had a burning desire for someone to tell me it’s all going to be okay and to show me how to be happy.

Most things I read about depression leant toward the word meaning something far more severe. Some say it’s a medical disease and, by the sounds of their symptoms, it seemed like they had something far more debilitating than I did. And some say that it’s a normal part of our emotional cycle to feel up’s and down’s and labelling the feeling of being stuck in a rut as depression is therefore false.

Whatever this feeling was, it sucked. I wondered sometimes if others feel the same way.

If so how do they deal with their emotional roller coaster? How do they push themselves to achieve their goals while still staying happy? I’d think.

Entrepreneurs Depression

I like to think of these low feelings that I was experiencing as Entrepreneurs Depression: the emotional anxiety and depression experienced when striving to achieve one’s purpose.

Notice how I mentioned one’s purpose?

That’s because I don’t believe every person who’s trying to build an online store like I was or any such other business, has the same drive.

For myself, it was more than a passion. It was my purpose. I HAD to do it!

Others who are just passionate about building an online business may not experience these same feelings which is great but can also work against them in a way that they don’t have the “back against the wall” feeling of having to achieve their goals no matter what.

How I Overcame Self Doubt

Since beginning my journey I’ve consistently educated myself with books, podcasts, courses, blogs and with friends.

Here are just some of the methods I use:


On days when I was feeling low I’d write down my thoughts as part of an exercise to label the emotions and separate them from “I am” to “I’m feeling”.

For example; when experiencing entrepreneurs depression it’s all too easy to think “I’m depressed”. The reality is that our emotions are in a constant state of flux and therefore you can’t be an emotion – you can only feel an emotion.

By taking a step back and looking at the feeling for what it is, I could see that it was an emotion that I was experiencing and it wasn’t me.


Tim Ferriss says that 80% of the high-level achievers on his podcast regularly take part in some sort of meditation routine.

I’ve tried a few different meditation programs like Calm and YouTube videos. What I found that worked best for me is the Headspace app from Andy Puddicombe.

I try to get up before my daughter Issy each morning and use the Headspace app for 10 to 15 minutes before my day begins. I’d honestly rate Headspace as being one of the best self-investments I’ve ever made.

headspace meditation screenshot from Matt Scott's phone


If you’re lucky enough to have a significant other that is supportive of your goals like I do, open up speak to them. Ask my wife any day–I’m an Ogre when it comes to talking about anything emotional. I really don’t like talking about feelings or any of that mushy stuff at all! But, hey, it works! And if nothing else, it helps bring your relationship together 🙂


As with anything, balance is essential. Too much of one thing will cause the system to crash. Be sure to try and factor in time for health, family, fun, learning and work.

Matt and Issy at Chiang Mai Zoo

Matt and Issy at Chiang Mai Zoo

Stoic Philosophy

Something I never thought would help but has since become a favourite is Stoicism. Stoicism can be described as an ancient Greek philosophy that teaches the development of self-control as a way of overcoming destructive emotions.

Some of my favourite resources for stoic thought are The Tao of Seneca: Practical Letters from a Stoic Master‎ and The Obstacle Is the Way by Ryan Holiday.

Why Am I Sharing This?

So there it all is. I’ve shared some of the deeper darker thoughts that aren’t comfortable to talk about. My honest hope is that at least one person will find this, try some of the methods I’ve suggested and know that they’re not alone in their feelings of self-doubt.