*Disclaimer – I have nothing against specialised careers. They are integral to our society (Doctors/Lawyers/Scientists). I simply believe there are too many people that fall into these careers for the wrong reasons. Let me tell you why you should keep your day job when changing careers.

So what do you do if you happen to find yourself in a specialised career  that you have fallen out of love with? Most fall into two categories:

  1. Continue working the same job
  2. Take the leap of faith

Let me expand on these two:

Stay On Course

Insanity is repeating the same thing – over and over and expecting a different result – Albert Einstein

If you are not satisfied with your career today, what makes you think it will be any different in 10 years time if you continue along the same path? Is the 10 years you’ve spent considered ‘experience’, or is it really 1 year of experience repeated 10 times? And what if new technologies come along that have the potential to automate your job?

Staying on course leaves you at mercy to external factors you have little control over. Like any good business must learn to adapt or die, you too should adopt this approach to your career development.

Staying put and feeling like this poor tiger? Do something about it!

Staying put and feeling like this poor tiger? Do something about it!

Staying on course year after year in a job you gain little satisfaction from, will slowly drain your creative spark and make attaining true mastery difficult. I really dislike the word “passion” and believe the self-help industry bastardised the word, BUT if you don’t like what you do, you are running a race with a considerable handicap. Your dissatisfaction is your body’s alarm-system telling you to pursue work that better aligns with who you are. Listen to it.

And here come the excuses/rationalisations for staying put:

I have kids to feed and mortgages to pay

I studied 5 years for this degree, I need to put it to use

My college debt is through the roof, I’ll just work for another 5 years in this job until I can pay this off.

Of all the poor choices you could make in life- neglecting your own development tops the list. Just like in an airplane emergency – you need to secure your own oxygen mask first, before helping others. Life will not get easier in ‘a few years time’ – there could be another GFC, your wife could leave you, your job could be made redundant – you simply don’t know what’s around the corner. So start planning now.

In today’s climate doing nothing/staying on course is one of the riskiest moves you could make (with little-to-no payout). As tempting as it is to get up and quit, keeping your day job when changing careers will ensure a smoother transition.

Take the Leap of Faith

(NB – Before discussing the leap – you need to be certain it’s your line of work that is the cause of your dissatisfaction, NOT your boss or work environment. Have you tried performing the same job in different environments, if so- did you regain the sense of purpose? If the answer is Yes, then I’m sure you know the next steps to take 😉  If the answer is No, despite working with awesome people – then you can continue reading. ) 


Then we have the more impulsive on the other side of the coin who can’t stand working another day at their job and accept the next job that is offered.

The leap of faith is something that gets glamorised in the entrepeneurial circles. Tired of your current job? Quit your day job and become your own boss. Take the leap – life is too short, sink or swim etc etc.

The very term ‘leap of faith’ should raise some flags in itself. I sure as heck don’t want to leave my livelihood up to ‘faith’, and jump blindly into the abyss. This mindset is careless and can lead to much unnecessary trauma. This is why you should keep your day job when changing careers.

Making the leap without doing your research or properly understanding the industry is like blindly jumping into waters without first assessing the depth, or what objects could be lurking below. You need to be adequately prepared and test the waters before considering the change.

What I did

I don’t claim to be the authority of what the best course of action – I can only speak from my personal experience.

I loved business, I loved selling and I loved the startup world. I thought to myself five years ago; What value could I offer these tech-engineers who build these amazing products? What skills did they lack?

Selling their tech products. Now the cynics here would say that a good product sells itself, and whilst I agree with this – to take a product to the next level you need expert salespeople to help convert interest into revenue, know targeted outreach and better understand your users.

So for four years I was working after-hours getting my hands dirty in digital marketing and sales. I had founded a startup, working for other startups on an equity-only basis, doing online courses and getting qualified – all while working my usual 9-5 job.

I was able to understand the type of work and whether it suited me before taking the leap. That four years also gave me enough time to build up my skills so I could provide enough value to businesses that I could be employed on a full-time basis. During this time, I kept my day job to pay the bills and de-risk my exploits. 

This meant sometimes I worked 70 hour weeks between all these ‘jobs’, seven days a week. But the projects I took on, (like writing this blog) never really felt like ‘work’ and I would immerse myself for hours before looking up at the clock and seeing 2am. This is when I knew I was on the right path.

Instead of taking a leap of faith and jumping off the edge into a new career- I stepped over a small crack in the pavement.

Do you think you should keep your day job when changing careers?

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