Dear Dr. Helen, how do I pick a career that’s just right for me?
Dear Dr. Helen, how do I pick a career that’s just right for me?

career change is hard, must look forward, not backFalling into negative ruts and difficult breakups … and I’m talking about career problems, not romance gone wrong. I’m talking about the places where we work and the careers that we pick which sometimes feel like a doomed relationship, and with bad patterns that repeat themselves.

Have you ever heard someone say, “I keep picking the wrong guy/girl”? Or, do you cringe on the inside while watching your close friend’s terrible relationship choices play out in a predictably unpleasant manner? What if we make similarly poor decisions when selecting our careers? Do we make unwise, impulsive choices when it comes to pursuing employment that can ultimately affect our livelihoods and professional development the same way that a bad romantic relationship can spoil our happiness? The short answer is yes. I have come to realize that picking the right long-term career can be just as impactful as picking a compatible life mate.


If your work history feels like one bad break up after another or you’re not getting the success that you want, then read this Q&A.


Q1.  You have put careers and romantic partnerships on a fairly equal footing. Why do you make this comparison?

A1. Too often, in magazine articles and advice columns (e.g., Dear Abby) which are mostly geared towards women and girls, there is advice about how to pick the right guy, or how to know if that person is ‘the one,’ and even how to get that person even if they seem unattainable. So much emphasis is on ‘picking’ the ‘right’ relationship to attain a happy life. But what isn’t discussed nearly as often is how to pick the right career path. These days most families need two incomes to be comfortable enough to have some financial security. Even when we are happy at home, having a miserable existence at work, where we spend most of our working hours, dampens our spirits. Unemployment, underemployment, and precarious employment are extremely stressful and normally coincide with lower earnings. Conflicts around money are one of the biggest problems which lead to divorce. The good news is that it’s usually easier to improve a career situation than it is to improve a romantic relationship.


career choices are hard - how does one choose?


Q2. So, I’ve heard that most people require at least 7 jobs or more in their lifespan. Is that a sign that they aren’t picking the right career?

A2. Yes, you’re onto something. According to Workopolis, “Canadians can expect to hold roughly 15 jobs in their careers.” That article goes on to say “The most common reasons people gave for changing career paths were discovering a new field they were passionate about (35%), becoming bored/disillusioned with their original work (24%), and setbacks such as lack of advancement and/or cutbacks, layoffs in a career path (19%).”

I believe there is value in gaining work experience by trying out different work environments and roles. Likewise, it’s often wise to date a little rather than marry the first person you go out with. With that said, most people already know what they are drawn to – both in their personal and professional lives. However, not everyone is equally skilled or self-aware and may not know how to go about it. That’s we here I come in to help, sort of like a matchmaker but for careers.

I will also add that modern careers are more fraught than careers were in the past. A good education no longer guarantees a bright future due to issues like artificial intelligence, automation, and the rise in part-time/precarious employment.





getting into the right career requires actionQ3. Most people invest time, money, effort and emotional labour into their romantic relationships, and because of that, they have difficulty leaving a bad situation, even when they know it’s for the best. Does this happen with work too?

A3. I see this problem all the time with clients who have spent significant time and money acquiring a solid education with specific career goals in mind, but slowly realize that their job (or something about their role or work environment) doesn’t suit them. There are others who settle for a job that’s ‘better than nothing’ but was never satisfactory. Then, as time passes, they become pigeon-holed or type-cast in the wrong type of role. I’ve also had clients who have settled into a long-term position but after gaining years of experience they’re now way overqualified for their job. All these clients become disillusioned and uncertain about how to get out of a deep rut. That’s is why seeing someone like me can help a person gain a fresh perspective and make their career upgrade easier.


Q4. We sometimes hear people say they have no problem getting first dates, but they have trouble finding someone worth seeing for a second date. What would you tell someone who has no difficulty getting a job – yet they always feel like they get the wrong job?

A4. Just as I would say to a friend who complains they are good at getting dates but not really clicking with those dates, I’d remind them that it’s wise to have certain standards and expectations of what you are looking for – whether it is a relationship or a career. Regarding work, is it stability, a collegial environment, opportunities to learn and develop, fair/equal pay, a manageable workload, a reasonable schedule? These are factors worth considering.



Do you need help navigating the world of work? Contact Dr. Helen today for a free and confidential initial consultation by phoneemail, or via direct message on TwitterFacebook, or LinkedIn. If something urgent comes up, I’m also available by a voice or video on Magnifi, an expertise-on-demand app.

Have you ever wished you could get inside the head of a hiring manager? You can. Dr. Helen Ofosu is a Career Coach/Counsellor with a difference. She has worked for organizations to create hiring and screening tools. She’s created countless pre-screening tests, interviews, simulations, and role plays for organizations of all kinds.

Dr. Helen’s training in Industrial and Organizational (I/O) Psychology means she is a genuine expert in evaluating work-related behaviours. She uses those skills to help hiring managers tell the difference between people who say the right things during interviews and people who actually deliver on the job. In other words, Dr. Helen understands first-hand how job candidates are assessed.


More than career coaching, it’s career psychology®.


I/O Advisory Services – Building Resilient Careers and Organizations.


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