Should I stay or should I go? Great song, lousy career strategy
I often found myself pondering about leaving a job, and many of the people I work with are battling with the same dilemma. Let's explore my recommended approach to thinking about it rationally.
In my practice, I often support people considering whether to leave their current job for something else.
As this is a recurring topic, I want to share the general principles I follow to approach that question in today's article.
Ideally, this will help many other people think rationally about the dilemma and devise a clear plan for addressing it.
Starting from the wrong question
Many people start their thinking around this problem with the wrong question:
Should I leave my current job?
The problem with beginning with this question is that it starts from a negative perspective: we focus our attention on running away from something rather than clarifying where we want to go.
We fixate on things we don't like in our role and naively assume we will not find the same issues elsewhere. The grass seems greener elsewhere, especially when we rely only on companies' public images without having clear insights into their internal operations.
Some clear disqualifiers might make running away from a workplace an excellent short-term goal; we'll discuss them later.
But in most cases, we fall back on considering all the negatives of our situation because that exercise is much easier than taking the time to clarify for ourselves what we really want. There is something comfortable in being consistently dissatisfied about your situation: it makes it look like it is someone else's fault. There is even a name for that: the victim mindset.
The problem with victims is that they give up control of their life choices, which only contributes to making them more miserable.
Before you settle for “I don't like it here anymore, let me go see somewhere else” as if your career was just a real-life slower incarnation of doom scrolling on social media, I recommend you take some time to ask yourself some other questions first.
Without clarity on where you're going and why, rage quitting will only provide a momentary relief driven more by the excitement of novelty than actual growth.
The right question to begin with
I'm becoming a broken record on this, but I believe the right way to decide whether to change your job should start with some solid lifestyle-centric career planning. I've discussed it more in detail in a previous article1, but the essential idea is quite simple: start by defining a clear vision of the life you want to live and then make your job a way to support it.
Instead of sacrificing many aspects of your life to support a career, you should choose one that supports your ideal life. Unless — of course — the life you want to live is where your job is the foundation for everything else.
Your choice.
Or rather, make sure it's your choice, not something you do to adhere to an externally imposed model of success.
More money and more prestige are often the crappy default we're served, and conformism is just a less radical incarnation of the victim's mindset.
You might not always be complaining, but you're still giving up a big chunk of responsibilities for your future.
Follow-up questions
Once you know where you want to go, you should go through a series of questions that take you from where you are to what your next steps should be.
What are your skills? What are you good at?
This is the career capital you've been building up until now. You can deploy these skills to generate value for potential employers or clients.
You should be aware of what makes you valuable and take the time to complement your own observations with other data points: ask people around you, rate yourself on the work you're doing, take online tests, etc.
What you discover might surprise you. You might find that you're good at things you never thought of as skills you needed to build.
For instance, one of the skills I'm valued for is my ability to speak the business language while still being a respected technical leader. This isn't something I added 20 years ago on the list of things I wanted to get good at. It was indeed not something I was passionate about. However, as I progressed in my career, I realized how valuable that skill was in the roles I covered, and I had to get better at it out of necessity. And it turns out that if you become good at something, you start enjoying it more. You often develop a passion for something because of getting better at it.
Do not judge your skills for how cool they sound or how much they correspond to an internal image you might have of your ideal job. Evaluate them based on the value they generate and the opportunities they can open up for you.
Are you learning new skills at your current job?
If the answer to this question is a clear no, then you have a problem. Moving away from your current role is a potentially good short-term strategy in such a situation. Have a look at the disqualifiers section below if this is your case.
If the answer is yes, then ask yourself how those new skills can help you achieve your ideal lifestyle.
For example, suppose your ideal lifestyle is to be a serial entrepreneur because you resonate with everything it entails. In that case, you might appreciate the opportunity to learn skills that push you beyond your comfort zone of technology leadership: marketing, sales, communication, and finance. You name it.
Conversely, suppose you aim to become a renowned expert in a particular domain. In that case, you might appreciate opportunities to develop further in that field, such as publishing papers on the topic or participating in conferences.
Those two sets of skills are not better or worse in absolute terms but only in their ability to help you achieve your goal.
What are the skills you'll need to accomplish the vision you have for your life?
You'll need to survey the world around you to answer this question. Be wary of the temptation of coming up with your self-defined narrative of what it takes to get there, as that's often delusional.
Find people who seem to live a life you resonate with, and study their life and trajectory. How did they get to where they are? Which skills were instrumental in helping them build the kind of life they're living?
This is one of the advantages of living in our current times: you can find plenty of information about virtually anyone online. As creepy as it sounds—and as it is—using such information to shape your life is a respectable way of leveraging today's approach toward privacy to your advantage.
Bonus points if you tell these persons via a non-intrusive message that you found inspiration in their journey.
Once you've figured out what you'll likely need to become good at to achieve your vision of a well-lived life, you're ready to move on to the next question.
What job will help you build those skills?
A somewhat cynical way to characterize a job is learning with someone else's money.
There is some truth to that, as in most jobs, part of the time you're paid for goes into learning new skills. There is nothing wrong with taking advantage of this situation, as companies will collect the benefits via the additional value you'll deliver.
Are there ways for you to cultivate those skills in your current job? If so, go for it.
There are things you don't like about your current situation, which will be true anywhere, but you have the advantage of knowing them. The grass is not always greener elsewhere, and saving yourself the hassle of a lengthy onboarding can be a wise strategic choice.
If there isn't a straightforward way to build those skills in your current job, you'll know you need to look for that opportunity elsewhere.
However, at this point, you'll start your search with much more clarity on what to look for. Your search will be driven by the need to find chances to build and improve specific skills.
You might even get creative with that.
Building on the fact that operating in a familiar environment has the benefit of limiting surprises and uncertainty, you could consider creating new learning opportunities without giving that safety net up completely. For instance, you could consider moving to a part-time role with your employer and invest the freed-up time in side hustles that will allow you to explore and build new skills.
As long as you give up the rigid constraint of always making more money when you move to a new job, plenty of opportunities can open up for being creative while reducing the overall risk.
Disqualifiers
I mentioned earlier that some disqualifiers should make leaving your job non-negotiable. I classify them into three categories.
Abuse, discrimination, toxic environment. If you're in such a place, your wisest choice is to go somewhere else as soon as possible. Your mental and physical well-being are at stake; do not sacrifice them. You might want to look for an “OK” job as an intermediate step here: find a healthy environment that will give you the mental space to think more clearly about the future you want for yourself.
Values misalignment. There are plenty of examples of that. If you care about people's health, you will be miserable working for a company selling tobacco. Suppose you believe in finding peaceful political solutions to war conflicts. In that case, you might have difficulty staying at a company that sells technology to defense — or rather offense lately — departments. I recently heard Ryan Holiday say something spot on in a podcast interview: It's not a principle unless it costs you money. I couldn't agree more, and I recognize how hard yet necessary it is to live up to our principles.
You're stagnating. In her book, The Engineering Leader2, Cate Houston talks about the key difference between what your employer is renting and what they are buying from you. Your expertise falls in the former category: it belongs to you. If your current job is eroding your expertise — because you're doing low-impact busy work, because you're spending more time dealing with politics than getting stuff done, or because you've lost the ability to connect your actions with tangible impact — this is an excellent reason to start looking for alternatives.
When facing these disqualifiers, take some time to appreciate the right level of urgency to deal with them.
If, in the case of an abusive or toxic environment, your goal should be to get out of there as quickly as possible, almost at any cost, for the other two categories, you can still allow yourself the time to figure out where you should go and why before pulling the trigger.
One more thing before you go
Sometimes, people fixate on promotions as the main proxy for growth and achievement. I don't agree with that.
I'm seeing a surge of content promising that you'll get promoted quickly if you follow these five discrete steps or focus on these three different activities.
Many of those articles miss the critical point: promotion is not the ultimate goal. Even more so, if you achieve it through gaming the system rather than by working on honing rare and valuable skills that make you a better person first and potentially promotable second.
The goal should be to build your chosen life, not just follow some beaten tracks that someone else has laid out for you.
In his seminal book The 7 Habits of Highly Effective People3, Steven Covey warned about a growing presence of Personality Ethics in literature. They contrasted that with what he calls Character ethics. While the former focuses on quick fixes and the cult of image, he defined the latter as follows:
The Character Ethic taught that there are basic principles of effective living and that people can only experience true success and enduring happiness as they learn and integrate these principles into their basic character.
His observations are still relevant today, and I believe that following his advice is still the best way to build a rich and fulfilling life.
If you found this valuable
If you found this valuable, here are other ways I can help you and your company:
Contact me if you're interested in a Fractional CTO, Technical Advisor, or Board Member for your company.
Join the waitlist for the upcoming launch of my Group Mentoring and Coaching membership. You can read more about it in this post.
Work with me 1:1 as your mentor and coach. I love working with driven and competent people in their specific situations and providing personalized guidance, insights, perspectives, and support.
See the article discussing this in more detail as part of my productivity system.
I've covered this book in a previous article; check it out here.
