How to Know if a Career Change to Entrepreneurship is Right For You


There was a time where entrepreneurship was looked upon with a less than a savoury eye. It was essentially code-speak for, "I'm not exactly sure...but I plan on wandering for a while. And I expect to fail. A whole lot. Oh, and sleepless nights. Those too." Today, things have vastly changed — partly, in thanks to technology. If you've been hit with the enterprising bug (our condolences!), this article will outline how to know if a career change to entrepreneurship is right for you.

State of the Union

Right now, the rise in entrepreneurship is a significant catalyst to the general dissatisfaction most Great Britain workers feel for example. In a study of workers around the UK, here were the most compelling findings:

  • London workers were some of the most unhappy in their jobs, with 32% regretting their job/ career choice
  • 51% of these workers 'dream of being able to turn their hobby into a career'
  • Yet, 29% of Londoners and 44% of Edinburgh natives have a fear of making the 'wrong decision changing careers' 
  • A whopping 55% of Londoners (over half) feel that finance is the greatest barrier to changing careers, right behind 62% of Edinburgh natives and 76% of Cardiff residents

The antidote to these perceived 'barriers' — usually the result of what Steven Pressfield calls 'Fear' and 'Resistance' — is something entrepreneurs-in-the-making have in spades: They've mastered the "Art of the Pivot."

From changing tack midway through a pitch to investors to shifting gears between multiple companies — Greetings, Mr. Musk — pivoting on a moment's notice is the first thing to master. 

Ensuring Stability While Maintaining Flexibility

To leave a career midway, either due to job dissatisfaction or workplace disengagement (which, according to Gallup, affects up to 81% of workers today), when you're a relatively unknown regular Joe is one thing. 

To leave a career as the editor of Vogue for 17 years so you can basically go solo and design your own wedding dresses — that's a whole other kind of leap.

Knowing if a career change is right for you is not a cinematic decision where you see the light. It's a process that takes many steps. 

And, as J.K. Rowling says in her commencement address, 'Some failure in life is inevitable. It is impossible to live without failing at something unless you've lived so cautiously that you might as well not have lived at all.'

1) Go slow to go pro

Take it slow. Dip your toes in. Some individuals love the rush of diving headfirst into a new venture. But that's why it's called a 'rush' — it doesn't last. 

Source: Unsplash

If you've been thinking of turning a 'hobby' into a career, start to do some research into what that would look like were you to monetise. Where would your streams of income come from? If it's products you specialise in, build a prototype and see if there's a demand. If it's services you offer, take on just one or two projects per quarter. 

This is a stress-free way to gain some initial much-needed confidence, momentum, and experience

2) Forge key relationships

Begin now to identify those in your niche that are already successful. You'll want to reach out to them, through a friendly email, and ask for five minutes of their time, or simply pose a question. 

If you meet these individuals at a networking event or a conference or even a fair, let them know you're passionate about what they do and you'd love to treat them to lunch someday if they're ever willing to spend some time showing you the ropes. 

Believe it or not, those who have made it are always pleasantly flattered and keen to mentor, passing their knowledge to those who are now where they were once.

3) Gordon Gecko says...

While you're doing the above, start to put away a small stash called the 'Quit Fund' or the 'Startup Cash Fund' or whatever other creative terms you'd like to give it. 

Part of leaping into full-time entrepreneurship is to make sure that you've got a bit of a financial pillow that you can lean on when things get, well, lean. You're not planning for the worst-case scenario here, but you're also not jumping in blindly. 

Source: Unsplash

Take stock of what you have, what you owe and your monthly non-negotiables. This will help you with everything, from the micro-decisions of whether to incorporate and the macro decisions like how much monthly, quarterly and yearly revenue you'll need to bring in. 

4) Set up a support network

The psychological price of entrepreneurship can be particularly steep — and it's a fact that no one is talking about. According to a study by Dr. Michael Freeman, a clinical professor at the University of California, 30% of all entrepreneur experience depression. 

The best way to mitigate against that is to build a secure support network — and mind that it's outside of your friends and family. 

The number one reason why entrepreneurs experience depression is due to isolation: They need individuals who are themselves entrepreneurs and who understand the daily grind, challenges, and excitements that come with the territory. 

5) 18 months

Click on your calendar app and fast-forward to 18 months from now. If you mark this as your official 'Quit Date,' you have from now until then to do all of the above: dip your toes in, build a client base and revenue, get your finances sorted and create meaningful, like-minded relationships and connections. 

Besides this, the next 18 months should also be about building a reliable routine and setting boundaries around when you work on these one or two projects. Go at each with a beginner's or a learner's mindset, willing to go above and beyond and learn on the way. 

Source: Unsplash

Now take a moment to think about what you've just read. 

Did it seem strange to you? Read between the words.

Running beneath the meaning of most advice on 'how to make a change to entrepreneurship' is this idea that being an entrepreneur is about capital-R 'Risk': How to avoid it, how to mitigate it, how to shield oneself from it, and how to plan for it. 

It's called being 'strategic.'

According to the author, speaker, and serial entrepreneur James Altucher, it's the fallacy of staying in a job for the purposes of 'job security' or 'upwards mobility' that is the greatest risk of all. Altucher points to the shifting global economy, the rapidly shrinking, increasingly location-independent office, and AI to make the very pressing and solemn point: The only one you can truly bank you. 

So choose yourself. That's what entrepreneurship is really about. 



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