How to make wise career and job choices

Career and job decisions have a long ranging impact on our professional and personal lives. Learning how to make wise career and job choices is essential.

Health, wellbeing and success is at stake with the consequences of choices made in careers or jobs.  Whether they are positive or negative, choices will have repercussions across all areas of life and work.  

Even the most confident and experienced of professional candidates will face challenges in their quests irrelevant of being at $80K or $800K salary levels.

But irrelevant of sector or role, I estimate and have observed over the years that circa 50% to 60% of career and job choices will ultimately meet with a degree of regret and in hindsight, deemed unwise.

Remorse and unrest generally starts to niggle people within the first one to six months of starting any new role. Admitting a career gaffe to yourself is hard, but even harder to others.

Justify ~ Rationalise ~ Reassure

The precursor to a new role, promotion or career change which may be unwise are proclamations to justify, reassure and rationalise that decision.

Tuning to fervent attempts to convince and qualify choices (to self and others) is a strong indicator of misalignment and unease.

There are many moving parts, conflictual and emotional elements when in the professional and executive job search hot seat.   

Making wise choices for the right reasons lays a platform of self-confidence and a career trajectory that supports authentically.  But unwise choices will erode on many levels both consciously or unconsciously.

When a choice is a wise one there is a collective sense of harmony and excitement.  Harmony is instinctive and there is no need to rationalise, justify and reassure yourself or others of the decision.   And the converse as outlined above when a decision leans to an unwise one

Risky Decision Wheel

After sixteen years in recruitment and executive job search coaching I have observed time and time again the three key elements that contribute to making unwise job and career decisions.  

These damage and halt critical thinking keeping competent professionals on a treadmill of unhappiness and unrealised potential.  They can be individual risk factors or combined as part of a risky decision wheel:

Wrong Motivations

 There are many motivators when choosing a new role or career pivot.  But some can be so bright and shiny that the allure of them blindsides to other pertinent realities.

Money, prestige, fame, security, a great agency or organisation to have on the CV are big alluring and illusionary motivators.  And desperation can be deafening and can bite the proverbial hard.

Critical thinking is key to minimise deluded decisions that once the gloss has worn off may put you behind the eight ball.   It’s not the actual motivator that matters in singular form but the alliance with other factors and variables to consider.

We all seek to survive and thrive with the latter crossing over to making a real difference and impact broadly.  But if the motivators are purely monetary or selfish they may lead to unwise long term decisions and dissatisfaction.  A deeper analysis of your who, what, why will clarify wise decision making.

Sunk Cost Bias Fallacy

The impact of sunk cost bias fallacy is as prevalent as  often illogical and erroneous.  Essentially it refers to the hardwired tendency to follow through on activities, a course of action and  career where considerable cost (effort, time and money)   has already been invested.

We all have fallen into this rabbit hole in some way and for career decisions it begets the question if the current costs outweigh future benefits.  And those biases can be applied from family and community expectations to deliver also.

After long and laborious hiring processes the ego to win overrides wise decisions also.  Desperation and the desire to conquer often shrouds evidence.  Be mindful.

This is an excellent definition of Sunk Coast Fallacy from CIG which applies to all sectors and professions :

“There is a good deal of psychology at play when it comes to the sunk cost fallacy and why we fall for it. Assistant professor at Carnegie Mellon’s School of Business, Christopher Olivola, believes that there is a very specific reason we feel the need to “stick to the plan” when it comes to decisions. 

Olivola cites cognitive dissonance, a phenomena that occurs when we feel remorse after making a decision, as the main reason why we most often fall for the sunk cost fallacy. This cognitive dissonance often leads to defensive behaviour and thoughts in regards to an original decision –– but this emotional reaction could cause you to continue down a path that clearly isn’t working for you. “

Men are  often beholden to a career path that no longer benefits them and fear change due to investments to date.  I undertook  a survey in 2020 asking Mens Level of Work and Career Happiness and their decisions. The results and feedback was insightful.


Fear is more pernicious than realised and manifests in a myriad of ways.  Knowledge is power and without full knowledge wise job decisions are compromised.

Let’s be very clear, hiring and job search is a two way street, and particularly for senior leaders and managers.  Yet far too many candidates, irrespective of being at the $80 to $800K band  fall into the master-slave hiring pit.

Recruitment agencies, panels and hiring managers are equally complicit in the pit.  Holding a two way mindset must be understood that today’s candidate can be tomorrows hiring manager, and memories are long.

I have seen this play out so many times.  Strong leaders with stewardship over hundreds become acquiescent and meek in the hiring process. 

Negotiation skills, empowerment and fearlessness are hidden for fear of reprisals.  So candidates don’t dig enough, ask important questions and challenge for mutual value.  And it is of mutual value for all parties to learn as much as possible about each other.

Like an ostrich head in the sand, many choose not to ask the hard questions for fear the answers will nullify their interest.  This impacts across motivations and the reality of management styles and culture the role pertains.

How women approach job searching differently

Women are particularly fearful of putting themselves out there as indicated in the  2019 LinkedIn Gender Insights Report .

It was found that women will only apply for roles if they meet 100 per cent of the criteria compared to men who confidently apply if they meet 60 per cent criteria.



Many professional outstandingly talented  women pursue roles that do not fully capitalise on their value as they don’t put their hat into the ring to learn more in robust direct conversations.

Note    Job advertisements are mostly cut and pasted, poorly thought out and rarely share the reality of a role, the purpose of the role and what success will look like.  90% of JD’s are useless so the greater the need to have quality conversations at the front end to determine if the role is even suitable or relevant.

Further, perceived issues of ageism bias and fear to address those issues keeps both men and women from applying to roles.

Due Diligence  is a critical part of wise and risk prevention decision.   Reference checking is a two-way street.  Given the attrition of staff due to toxic management it is essential that as a candidate you dig deep without fear.

Always reference check the management, staff and culture.  LinkedIn, networks, Google and casual conversations are all part of the mix, just as they are for the employer.

Summing Up

There is no guarantees in careers and job choices. Minimising unwise choices and maximising wise decisions requires taking stock of your true motivations. Taking respectful control of the process and embracing a marketing curious mindset will fortify confidence.

And don’t ignore any evidence at the front end as rarely do situations improve. Don’t fall into the belief that it may be different for you despite contrary feedback.

Be brave, creative and persistent for your long term career happiness and wellbeing.

Suggested reading:  Strategies to Navigate Career Ageism   &  Navigating the Salary Dance

Career and job search services  HERE


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