From Unemployed to Entrepreneur

It’s one thing to hustle 3 months of freelance work, but how do you turn a brief reprieve into a life changing career?

Path From Unemployed to Entrepreneur

When I was called into an office one fateful day and told I was being down-sized, I suddenly had a new title.  Unemployed.  What was I?  Who was I?  My career plan had been wiped out, so now what?

When I landed my first contract, I had an income again.  I felt relieved for half a second, but I still needed to figure out a plan.  How would a new employer be any different than the last?  What did I really want?  I had a small taste of the flexibility of being my own boss; did I really want to return to the 9-to-5 grind, once again at the mercy of someone else’s whims and directives?

Long before I finished that first contract, I started hunting for the next revenue stream.  I was no longer looking for a full-time job.  As far as I was concerned, I already had an employer – myself!

And that was the mental shift that changed my fate.

I’ve had friends, many, who have lost their jobs over the years and who have gone on to other jobs.  Some went through a few short contracts or freelance work similar to the work I did when I first started out, but invariably they eventually found and settled back in to full-time employment situations.  That was their choice.  Along the way, if they didn’t have steady income coming in, they considered themselves “between jobs” or unemployed.

Since going out on my own, I’ve only ever considered myself to be my own boss.  It didn’t matter how many customers I had (or didn’t have), I was always working for myself.  I wasn’t unemployed, I was self-employed.

That was the very first step of a journey toward realizing my own dreams, instead of working on someone’s else’s.


Why Start Your Own Business?

I’m often asked, “why start your own business?” Why take the risk? Why not settle in somewhere with job security, as much as this even exists anymore.

I’ve said before that I’m an accidental entrepreneur. Or an accidental solopreneur and occasional entrepreneur. I’m not sure the label really matters. Basically, I work for myself. I have a business that needs to make money in order for me to have an income.

Many years after that first fork in the road, I’m still at it and haven’t looked back.

Accidental Entrepreneur

Before owning my own business, I was an employee for a large consulting company. Until my job went away. I suddenly found myself down-sized, and without a paycheck. It’s the worst feeling in the world.

I was very young at the time, had no savings and no plan.  Oh, one thing I had plenty of?  Debt. Thank you institutes of higher learning.

When I lost my job, after crying and taking a nap (devastation is apparently exhausting), I got on the phone. I called every client I ever worked with and told them I was now working for myself. Are you even supposed to do that? Who cares. I needed money to pay my rent so I wouldn’t end up on the street. Basic math.

So I called clients and asked them if they had any work. That was the hardest part. Have you ever had to do that?  Not submit an application through a web site.  But call someone and straight out ask them for work. Asking for work felt like begging.

At least it did to that version of me in that particular moment.

Never Looked Back

Years later I realize asking for work is just another name for ‘sales’. And clients expect you to ask. They want you to ask.

I spent 3 days making phone calls.  Lots and lots of phone calls. All of those phone calls led to 2 follow-ups, and that led to my first contract.

My (eventual) company grew from me being on the losing side of someone else’s coin toss. And the one thing I knew for sure was that I never wanted to be in that position again.

No one can accurately predict the future, but I want to at least be the first one to see what’s coming at me. When I worked for someone else’s company, I bet 20 (or 30 or 50) people knew my future weeks or months before I did. Now the only person influencing the road ahead is me.

Start your business and you are the boss

When asked why start your own business, I ask how many people can change your fate in a moment?

Does someone, right now, have the power to take away the means you have to support yourself?

Could everything you rely upon be taken away by a 15 minute conversation?