I decided to leave my somewhat secure job a few years ago to become an author and entrepreneur because I was fed up.

I was fed up of playing by someone else’s rules.

I was fed up having to say yes, when all I wanted to say was no.

I was fed up of clocking in and clocking out, and repeating this tedious cycle.

I was just… fed up.

I felt like I had more to offer, and I believed I could create a real impact in this world. Was I ready to leave my job and set out on my own? I had no idea (some days, I still don’t). Was I scared of the unknown, and the fact I couldn’t see or predict the path before me? Absolutely (most days, I still am).

But I made the decision to leave regardless, because I desired more. I yearned for more freedom, and I figured if I’m only given one shot of a life in this world, I may as well make it count.

I’m not alone in thinking like this. After interviewing 250+ people over the last few years, this is why most people chose the unknown over the predictability and security of the nine-to-five.

So if this is the case, why do so many entrepreneurs I meet feel trapped?

Why are they depressed?

Why are they still desiring more, even though they received ‘more’ the day they left their job?

There’s no easy answer to this. The reason why is different for everyone. But in my experience, this entrepreneurial depression happens when one or more of these three traits come into play.

1: You do the same thing day in, day out

If you want to do the same thing day-in, day-out… get a job.

There are literally hundreds of jobs that will give you this, along with a secure and predictable salary. You don’t jump into the unknown of entrepreneurship to do the same thing each day. You need a challenge.

Compacemy is a killer, so if you find yourself feeling complacent, it’s all the warning sign you need.

Because it’s a sign that you are not happy (and things need to change).

When I interviewed Thomas Frank for ‘The Successful Mistake’, he told me about such a period. While studying at college, he setup ‘College Info Geek’ in a bid to create some side-income and help his fellow students.

It took off. Month on month, he grew.

So he decided to cut down on his classes and studies, dedicating more time to his business. On the surface, this seems like a sensible decision. More time and resources equates to more growth… right?

In Thomas’ case, no.

He found himself with too much unstructured time on his hands. He went from motivated and challenged, to lethargic and complacent. His growth halted, and a plateau took its place. And it remained this way until he challenged himself once again, and made his life ‘hard’.

Because life is supposed to be hard; interesting and full of challenges.

2: You suspect you’re self-sabotaging your success

This is a tough warning sign to spot, especially if things are going well.

On the outside-looking-in, all seems fine. You have a successful business that makes you money; you have plenty of luxurious ‘things’, and you travel to exotic locations; your growth rises month-on-month, and you everything you want (at least, everything you wanted when you first began this journey).

Yet… you’re missing something.. You feel lacking. An empty void lies beneath the surface.

Jayson Gaignard felt this when he grew his ticketing business to one of Canada’s largest. He had it all: money, success, the big house, the nice car, the impressive network, the special invites to special events.

On the outside, Jayson must have seemed like a happy and fulfilled individual. But when I interviewed him for ‘The Successful Mistake’, he painted a different picture; a picture of self-sabotage and unhappiness.

With hindsight, Jayson now realises this ticketing business was his ‘Plan B’.

It gave him money and ‘things’, but it didn’t fulfil him. He felt like he could provide more to this world, and so he self-sabotaged his success until he lost it all. Did other people and factors play a part in his company’s demise? Sure, of course.

But much of it was down to Jayson, because Jayson wasn’t satisfied with where he was and what he was doing; and more important, where he was heading. So if you sense you’re self-sabotaging your success, chances are there’s a reason for it.

You’re not happy, and you won’t be until you replace your Plan B with Plan A.

3: Your hobby doesn’t feel like fun anymore

Many people build their business on the back of a passion or hobby. On its own, I have no problem with this. I believe you (to an extent) need to be passionate about what you do, but there’s a balance.

If all you have is passion… well, you may find that passion will desert you over time.

It certainly deserted Claud Williams, as he grew his photography and videography business while still at university. He started this business because he loved life behind the camera, but as more people wanted to work with him more often, Claud’s passion faded until all that remained was apprehension.

Again, I believe there is nothing wrong with building your business on the back of your hobby, but if you find yourself no longer finding your hobby fun (to an extent, you dread doing it), you may have a problem on your hands.

Because if you want to make a real go at ‘this’, you need more than a hobby; you need a business.

And a business requires purpose, as well as passion.

So if you experience one or more of these (now or in the future), don’t push it to one side. Don’t hope for the best and assume it will change. Take action. These are warning signs designed to point you in the right direction.

You’re not happy with where you are, and this is not okay.

Regain control, because you didn’t create your business only to become depressed because of it.

There’s another way, so face the music and find the solution (just like Thomas, Jayson, and Claud did).