Leaving a leadership position to start your own business
It’s a question many leaders find themselves quietly asking at some point – what if I just left all of this and started my own thing? And if that sounds familiar, you’re not alone. Plenty of leaders in high-pressure roles find themselves fantasising about a fresh start – often in a field they already know well. But is it the right move?
Firstly, if you’re feeling this way, know that it’s not a straightforward answer. You’re not the first leader, and you won’t be the last, who wants to pack it all in and go and set up their own business. I get it. I did it.
When someone asks if they should go for it, I always feel a bit too much responsibility answering a resounding ‘yes!’. Without knowing the ins and outs of your market, how good you’ll be at selling your services, and your appetite for all the hassles that can come with small business ownership (or even on the smallest scale of being a sole trader) then I cannot provide strong advice. But, there are ways to figure out if now’s the right time.
How can you know if it's a good idea?
Start with a few key questions:
- Is there a clear, established market for your idea?
- Are you confident in your ability to sell your services?
- Do you see a demand for you delivering these services?
- Are you ready for late nights, early mornings, tax returns and subscriptions to a hundred different services which you need for a website, a mailing list, etc?
If you’re answering yes to most of these, then you may be justified in thinking it is a good idea.
Don't jump too soon!
Push your leaving date as far down the road as you can. Whilst you are still drawing a full-time, reliable salary you should warm up your network, build your website, decide what your social media presence is going to talk about, draft some posts, and maybe even win your first couple of bits of work and complete them in the evenings and the weekends so you have something to talk about on your ‘clients’ page of your website. (Just check that your contract doesn’t forbid this as you don’t want to start your freelance life with a solicitor’s bill).
Don't check out early
One final note. If you’re still in a leadership role, don’t become a rubbish manager just because you have your eye on the door. Your team still needs you – you’re a primary source of development, mentorship and support in their working world and you are doing them (and yourself) a disservice if you don’t take care of these people. Showing up with integrity until the very end says a lot about who you are as a leader (and the kind of business owner you’ll be too).
Resources to help a transition to entrepreneurship:
How to leave well: Why the last 90 days matters the most
Some other questions to consider before going freelance (10 years old but the advice still holds): What do I need to work out?
Powerful, and surprising reasons you should leave a senior position: when quitting is your best option
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