Is Matching Personality to Money Earning Approach the Key to Long Term Career Happiness?

Is Matching Personality to Money Earning Approach the Key to Long Term Career Happiness?

Understanding your personality could be the key to finding a career that makes you happy in the long term. It seems so obvious, but here I am at 37 just figuring it out.

On the face of it, I’ve had a very successful career. I have received a very good and growing paycheque and I’ve progressed in title from one job to another. When I became unhappy at one steady paying job, I’ve been able to find a different one with a bigger title and large paycheque. So why do I constantly find myself unfulfilled, unhappy and asking myself “what do I want to be when I grow up?”

I recently stumbled upon a realization – that I’ve been asking the wrong question!

Rather than asking what I want to be or do, perhaps I should have been asking how I want to earn a paycheque. The answer to this question, one has to look at their personality and their values.

What I value more than anything in the world is individual freedom. Based on my favorite personality indicator test, the enneagram, I am a seven, which is often called an enthusiast. The seven personality can be described as spontaneous and versatile, preferring a wide range of experiences and variety. We get bored easily, are quick learners and move seamlessly from one activity to the next.

Based on the characteristics above, is it any wonder why my safe, steady paying jobs have resulted in me being unhappy? New experiences and constant variety are my jam, yet I’ve chased the safe and steady paycheque – the alluring money trap, which sucks you in and forces you to settle and the fear that stops you from taking the risks necessary to find your true calling.

The reason I say that I’ve stumbled upon this realization recently is because I’ve been helping my wife with her business – she has been busy being pregnant and bringing our twin boys into the world. She (with my help) has a Public Relations and Digital Communications company, CIPR Communications. As opposed to earning a stable paycheque month in, month out, she has to constantly find new clients and earn her living one contract and one satisfied customer at a time.

Working with her has opened my eyes to the fact that I’ve been going about earning a living in a way that is inconsistent with my personality and the things I value most.

In the past few days, I’ve changed the relationship with the company I’ve been engaged with on a “full time basis”. They are now a client of CIPR Communications, which gives me the freedom to work on other projects with other clients – this small but important change makes me feel so liberated and happy I can hardly contain myself!

I’m excited to find other clients to keep me engaged and to give me the variety I seek as a seven-personality type. While I will no doubt make less money in the short term since my engagement with my current company will not be full time, I am confident that the money will come in the long run and I know that the thrill of the chase for new clients will keep me excited and motivated.

Because I like a variety of experiences and people, I have also started working towards a real estate license. This will bring together my ongoing and long term passion for real estate (I’ve owed, renovated, flipped and rented several houses in my short adult life) with my need for constant variety and change (many clients, many houses, many interesting twists and turns around each deal). Between helping my wife with her communications clients (I also like to write, be strategic and creative) and helping my own future clients buy and sell their homes, I’m confident that I will finally get to a place where my method of earning a living matches my personality!

Are you happy in your career? Does your method of earning a paycheque match your personality? If not, I encourage you to find the courage to try something completely different – you might be surprised by the result!


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