“Should I Quit My Job And Pursue What I Love?”
Welcome to our mini-series ‘Ask An Expert’, where we connect you (and your dilemma) with someone who knows their stuff and can provide actionable advice to help you navigate the situation with ease. As the final part of this series, we have a career question from one of our readers. On hand to offer expert advice and guidance is Career Transformation Expert and founder of The Ascent Associates, Jo Glynn-Smith.
In the final part of this series, we’re tackling a question many of us have asked, especially in the age of side hustles and flexible careers.
The dilemma
I’m currently stuck in a job that pays well but leaves me feeling totally empty, and I can’t decide if I should try to turn my side passion into a career or if that’s just a fast track to hating the one thing I actually enjoy. Is it better to ‘do what you love’ for a living, or is it smarter to keep your hobbies as a fun escape so work doesn’t ruin the magic?
Jo’s advice
It really depends on what you want from your working life. Both offer advantages and challenges. A regular job is typically more financially stable than running your own business, which means you can structure a lifestyle around a guaranteed income and benefits. However, because you’re working for a larger organisation, you are not always in control of your time, the direction or culture of the business, or the type of work you do. This can be draining if you don’t enjoy the work, but if you do enjoy it, it can be incredibly fulfilling. Sometimes changing jobs can be the secret sauce we were missing.
As an entrepreneur, you are 100% in the driving seat and you get out of your business what you put in.
This requires a lot of self-motivation but can be extremely rewarding. With that autonomy, though, comes a lot less stability and structure – your income is never guaranteed, and this can be stressful and make planning really difficult.
A side-passion like yours is a great way to dip your toes into that entrepreneurial space without the risk. It gives you the balance between a job that pays the bills and something you genuinely enjoy. If we reframed your situation, you could say your job, whilst not ideal, supports your lifestyle and gives you time for your passion with low risk. However, you could also say that your job is taking energy away from your ability to commit fully to your dream. So, what’s it to be?
Try this exercise
First, let’s try a little visualisation exercise. Close your eyes and imagine your side passion is now your full-time job – what does it feel like when you get up in the morning? What does the structure of your day look like? Whom are you interacting with? Where would you be working? What do you need to do more of to get the business up and running fully? What challenges are you likely to come across? What will it feel like to work on this day in and day out? What are your strengths, and which areas of running a business are you less confident about? What will you need to learn? Try to focus on the feeling of running your business.
Do you feel excited and motivated, or scared and overwhelmed? This will tell you a lot.
Make it real
Then look at the practicalities of leaving a secure job and do a financial plan. Review your current income, your outgoings, your savings, your partner’s income (if you have one) – how will you manage financially through this transition? What will you have to sacrifice to build your dream? How much time will you give yourself to see whether it’s working? Do you love your passion enough to give it everything?
Final thought
These exercises are designed to give you a little more awareness around your situation and perhaps your answer. Ultimately, you are the only person who can decide which is the right direction for you, but clearly, something needs to change. Good luck!
Want more? See Jo’s other advice for what to do when your friend becomes your boss, or when you feel like you’ve been long overdue a promotion.
