How to create your own career path through entrepreneurship

When my dad retired from his job a few years back, he had spent 30 years in the telecom industry at the same company. The last 15 of which, he had spent dodging various layoffs and switching teams, as the telecom industry re-organised itself, spun off subsidiaries and re-aligned.

For him, creating his career path was a combination of finding out how to “not get laid off” every couple of years and proactively finding areas within the company where he could be useful. 

I, on the other hand, have spent less than two years working for the same company (and the longest time I’ve been at any single company is my own!). Much of my own career path has been building it myself through entrepreneurship.

Most people think “starting your own business” starts with quitting your job (and this post should probably be called “how to quit your job and start your own business.”). This post is not titled that. This is about creating your own career path through entrepreneurship, and the very first step is the opposite of what you’d probably expect.

Don’t quit your job

Most blogs like this would tell you, “Step one: quit your job.” This is terrible advice because now, instead of having a job and working on ideas to see what works, you’re unemployed, burning your runway and not sure if your idea works.

Not good.

If you’ve got a job that you don’t hate, you’re actually in a pretty cushy situation. You can show up, give them 40 hours a week and collect a pay cheque every two weeks. In the other 80 hours / week, you get to sleep, spend time with family and indulge your hobbies.

If you want to quit your job, instead of quitting right away, use the time at your job to keep collecting a pay cheque, build a runway to start your business and use your free time to start experimenting with different business models.

Here’s how you do it:

Put your skills to use

Whatever you’re doing right now in your normal job, start doing it outside of your nine to five. In other words, take the skills you already have and sell them to someone else. 

Think of it like this: Your employer is buying 40 hours of your skill / week, but he’s only buying 40 hours. You can work more than 40 hours / week and sell those additional hours to other people outside of your employer.

What you’re doing here is essentially diversifying your employment income (and increasing it), without even leaving your job.

Best of all, suddenly you have options. 

When I started IMPOSSIBLE, it started as a blog that I was writing while I was working full-time. I wouldn’t quit my job until two and a half years later!

Make your first $1,000

Okay, now that you’ve started looking outside your nine to five for options to make more money, start selling yourself.

If you have a business idea, start vetting it. If you don’t have a business idea, literally just sell your skills as a “freelance” artist.

You can do this very easily on sites like, but you can also do it by approaching other people that need services your day job might offer (but aren’t necessarily ideal clients for your employer).

For example, when I started consulting with start-ups through Impossible X, I took clients on a lower retainer basis with a performance incentive. These deals were too risky for my employer to take on, so there wasn’t any conflict here, but they were great clients for me to start to build my base.

Once you get a couple clients, set a revenue goal - a great number is $1,000 or $1,500 per month - and a time limit for each project, business or consulting idea you try out.

If you hit the number (remember, make this a real cash number), then you can assume you’ve validated your business idea. If you really like the business, but can’t hit the revenue goal, then re-think your approach.


All right. Now that you’ve proven the concept, you’re making money and you have actual, paying customers, you can think about quitting.

Now, if you do this before you replace your full-time income, you might have to downscale your lifestyle, but it’s also true that you might not even have to actually quit. You could potentially do your nine to five during the day, run your side-hustle in the evenings, and pull in a double-income if you like.

The call is yours, but again, the main thing here is that you have options. And if you hate your job, you now have the option to jump ship.

Double down

If you quit, you need to make sure that you can support whatever lifestyle you want to live.

This varies for everyone, but a huge marker is replacing your full-time income. If you do quit, you’ll have 40 hours per week extra to focus on increasing your income.

Remember, if you’re out of your job, you have to make this work. A lot of people celebrate a bit too much about the quitting and forget to make their business sustainable. Instead of focusing so much on quitting, focus on doubling down on your business, making it sustainable and then scaling it.


Now that you’ve got your job out of the way, you have all the time in the world to focus on your new business.

Now is the time to scale. While it might pay the bills at the moment, you don’t wanna be eating ramen and sleeping on the floor of your buddy’s place the whole time.


Once you get to scale with one business, instead of taking the money and putting it in the stock market, continue building your assets either within your current brand or as a new one.

In my business, once I scaled IMPOSSIBLE to a point that I was happy with, I found many of our projects in the paleo nutrition space were separate. I spun them off into their own company and began to build a team to manage it and build products (like our meal planning service) that diversified our revenue streams and started to protect the business a bit more. 


As each business begins to run itself (if you do the work to build and manage each team), then it frees you up to start a new business if you like and keep the cycle going.  

I’m at the early stages of this in my own business, but if you follow this process, you can build on each success and continue to build not only your own career path, but your own empire. And you can do it however you like. 


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