Solo Entrepreneurship

It was June 1st last year when I finally took the big leap. I didn’t have a job anymore, and I didn’t intend on having one anytime soon.

I had been waiting for this day like a 7-year old for months. Now that I could pursue my “calling” on a full-time basis, I knew that my life would be nothing short of extraordinary. Following the old adage, I was finally going to do what I love, and hopefully never “work” another day in my life. Fulfillment and abundance, I believed, were just a few moments away.

As you can imagine, that’s not really what happened.

Leaving the structure of a corporate job is not an easy transition. As appealing as the idea of complete freedom can be, having all the time in the world can swallow you alive like shifting sands.  With months of nothingness ahead of me, the perils were many: lack of clarity and focus, procrastination, slow implementation, and ultimately, running out of money. To make the matter worse, I had several projects on the go and I was seriously at risk of not finishing any of them.

But I was hopeful. Soon, I would reap the rewards of having the courage of my convictions. Of taking big risks and following my heart. I somehow believed that the universe would conspire to help me as I would progress along this noble path.

After spending a few weeks catching up on sleep, it was time to get to work. My hope was that by then, inspiration would find its way to me and that I would feel excited to start working on my projects. But I didn’t. Instead, I felt sluggish and unmotivated.

For entire weeks, I waited. Nothing came. No grace, no inspiration, no desire. Five months went by and I still hadn’t taken action. I spent entire days thinking about my business and reading about every aspect of it, but I still couldn’t get started. I was paralyzed.  

Freedom and creativity come at a cost, and going solo to start a business or pursue a creative career has its own set of challenges – challenges that were completely new to me. In retrospect, my hurdles stemmed from a romantic vision of solo entrepreneurship. I had made this idea up in my mind after listening to countless stories of successful entrepreneurs. But those stories don’t tell the entire truth, and the vision I had turned out to be completely unrealistic.

Luckily, I figured out what was wrong with my approach and finally got started. And here’s what I learned along the way.

The challenges of going solo

In business, what matters is not the ideas you have, but how well you execute them. And successful entrepreneurs usually have two important strengths: self-motivation and discipline. But those qualities are not innate – they are the fruit of constant effort and dedicated practice. I had not realized that a decade in the workplace, where all my work was structured around deadlines and accountability, had killed my ability to self-direct. My motivation to get work done was only external, and my self-discipline was terribly weak.

Now that I was on my own, there were no more carrots and no sticks. Yet, I still needed to find a way to sit down and get the work done. I eventually learned to redirect my attention inward and base my productivity on internal cues. But first, I had to debunk some of my own misconceptions about going solo.

Myth #1: I can’t start my project because I don’t have enough time.

I am a multi-passionate person with multiple projects (at the idea stage) on the back burner that, I like to think, I will execute “when I have more time.” Clearly, with a full-time corporate job, I didn’t have enough availability to get those projects off the ground. Sound familiar?

That was a lie.

If the problem had been solely lack of time, I would have been faced with incomplete projects. The fact that I had not even started any of my projects was symptomatic of another problem. Lack of time was only my excuse for not getting started – it was not the cause.

The real problem was that I didn’t want those projects badly enough. My motivation wasn’t grounded in my values and I couldn’t justify the effort involved. Let’s take the example of the book I wanted to write. After a little soul-searching, I realized that my underlying motivation was my desire to acquire status in the creative field. I was attached to the idea of becoming a published author, which would have been the ultimate sign of my successful transition toward a creative life. But I was not really committed to putting in the effort to achieve that goal.

Once I had no more excuses, the lie I had been telling myself became blatantly obvious.

With time, I became better at discerning my true motivations. I discarded the projects that were driven by ego, and rather than committed to the ones focused on the journey rather than results. That freed up the mental and emotional space to commit to doing business for the next few years. Because it became clear that more than anything else, I wanted to make a contribution to the world and develop the perseverance and resilience it takes to make a difference.

Being honest about  my motivations and choosing process over results resulted in a major breakthrough, and that’s when I finally got started with my business.

Myth #2: Creative work comes naturally to those who are called to do it.

Creativity and resistance are two sides of a coin, just like risk and fear are inseparable. And starting a creative career or a business inevitably comes with massive resistance, especially if you are following your calling.

As Steven Pressfield wrote in The War of Art:  

There’s a secret that real writers know that wannabe writers don’t, and the secret is this: it’s not the writing part that’s hard. What’s hard is sitting down to write. What keeps us from sitting down is resistance.

When you go solo and want to create anything, resistance is the enemy. No matter how noble your pursuit is, you will be held back by resistance in one form or another, whether it is distraction, procrastination, or chronic lack of focus. I experienced the whole array of resistance manifestations: excessive Facebook browsing, chronic oversleeping, obsessive dating, overtraining, overeating…

The first step for me to deal with resistance was to realize that it would not go away. All I could do is get used to its unpleasant presence. Then, I realized that resistance only beat me when I wasn’t fully aware of its presence. Its favorite tactic was to take me by surprise. I figured that the best way to fight it back was to keep it within my sight at all times. So I confronted it, and wouldn’t let it ruin my day without putting in a good fight.   

I did so by committing to a stringent morning routine, one that would be hard and that I would resist. The routine was simple: upon waking up, I would run 5K, meditate for an hour and journal two pages. Then I would go on with my day. But simple doesn’t mean easy.

And surely, every day when I opened my eyes, resistance reared its head. My morning routine became my daily wrestling practice with resistance.

And it was hard. Really hard. But I stuck to it, for almost a year.

Did it get easier over time? Hell, no! Even today, every morning is a battle to get up and get out the door. But I have reached the point where I don’t expect it to get easier; I just keep looking at resistance right in the eyes and going anyway.

Following a morning routine has been an effective antidote to my inertia and lack of motivation. The structure and discipline I gained from my daily practice has helped in all areas of my life. I’m not exactly a dynamo when I run in the morning – just like I’m not always ecstatic when I work on my business – but that doesn’t matter so much after all.

What matters is to keep going anyway.