Changing or quitting careers is hard. Doubly so in midlife. Should I quit or stay? I grappled with that question for almost 2 years.
In early 2021, I walked away from a lucrative engineering manager role and a 20 year career to start my solo practice. The decision didn't happen overnight. Neither was it easy or obvious. Often it was gut wrenching and confusing as hell.
I also realized no spreadsheet will ever help me make the decision. If anything spreadsheets make it harder — the numbers can be mind boggling to voluntarily walk away from.
Looking back, it was a series of small decisions that eventually added up. And these could be traced back to a key framework or mental model I had read, discussed, or stumbled upon. Fortunately I kept extensive notes.
In this article I share 35 frameworks and mental models for a midlife career change that helped me get out of my own way.
Cutting the gordian knot of our thinking
Quitting or changing is especially difficult when you are a well-paid professional with 15 plus years into a career. We are paralyzed by the weight of the decision.The stakes seem too high to even consider a change let alone making one.
And when we do try, we go down the same neural pathways never really getting anywhere, and stuck in a quagmire of mental cobwebs with no clarity.
Fortunately, some of the greatest minds from Franklin to Bezos have been grappling with the same questions. Hopefully these frameworks will help cut through the knots of your choices and indecisions.
Some pointers when considering a midlife career change
Before we jump into all the frameworks here are some key considerations:
a. Limbo is a drag on performance
Optionality is not always a positive. Having the option to walk away but never exercising it can grind at you. The default has an invisible price when we are ambivalent. Quitting is not the only answer either. Deciding to stay and not entertaining other options can in itself be liberating.
But the worst thing you can do is stay in limbo. Making a decision either way and owning it outright is underrated. Instead we tell ourselves that we don’t have options.
b. Look for frameworks rather than answers
One time-tested device that can help break the logjam is a question or framework designed to help see the situation anew. They are not necessarily answers, but different orientations to look at our quandary. They question the very questions we are asking, and can give a different vantage point with different views and different answers.
c. Design a compass rather than a map
By definition quitting a job or starting something new means unknown territory. And in unknown, unexplored territories, maps or prescriptions are not helpful. What’s more helpful instead is a compass that helps to orient and explore the terrain.
d. There is no right answer
I don’t glamorize entrepreneurship. Neither am I convinced by the creator economy or fire movement. There is no right or wrong answer when it comes to making difficult choices. The only right answer is whatever we in fact end up choosing. Not exercising our choice is when we feel powerless and frustrated.
35 of the best frameworks and mental models for a midlife career change
1. Choose enlargement over happiness
Oliver Burkeman shared this framework in his last column in the Guardian:
When stumped by a life choice, choose “enlargement” over happiness…. major personal decisions should be made not by asking, “Will this make me happy?”, but “Will this choice enlarge me or diminish me?”
We’re terrible at predicting what will make us happy: the question swiftly gets bogged down in our narrow preferences for security and control. But the enlargement question elicits a deeper, intuitive response.
You tend to just know whether, say, leaving or remaining in a relationship or a job, though it might bring short-term comfort, would mean cheating yourself of growth.
Relatedly, don’t worry about burning bridges: irreversible decisions tend to be more satisfying, because now there’s only one direction to travel – forward into whatever choice you made.
— Oliver Burkeman
2. Choose trajectory over optimization
When making long-term decisions it’s more useful to look at trajectory. While in temporary absolute terms quitting might not be smart, what does your overall life trajectory look like?
Are we optimizing the short-term at the cost of a more compelling and satisfying long-term? Are you optimizing for this year or for this decade? Is it helping or hurting your intended trajectory?
Long-term thinking levers our existing abilities and lets us do new things we couldn’t otherwise contemplate. It supports the failure and iteration required for invention, and it frees us to pioneer in unexplored spaces.
Seek instant gratification—or the elusive promise of it—and chances are you’ll find a crowd there ahead of you.
— Jeff Bezos
What good is it to be optimizing but in the wrong direction? Given a long-enough timeframe, small actions can have outsized effects. Are you giving yourself enough time? What assumption of time are you making?
3. Foresight is limited. Hindsight is unlimited.
We have a little of one and an abundance of the other. The mistake is to wish for more foresight. It’s not coming.
Life can only be understood backwards; but it must be lived forwards.
- Soren Kierkegaard
Many of the actions we think of as mistakes did not start out as one. They became one only in hindsight. They started out the same as any of your other successful moves. Just because it didn't pan out, does not mean it was the wrong decision.
In wanting to take the leap and start in a new direction I wanted a "proven solution". A guarantee that it would all work out. There isn't any.
Uncertainty can be a hard one for STEM professionals. We work to stamp out unpredictability which makes it harder to embrace uncertainty proactively as opposed to circumstances or someone else imposing it upon us.
4. Anxiety or ambivalence is the wrong criteria
Our anxiety does not empty tomorrow of its sorrows, but only empties today of its strengths.
— C H Spurgeon
Anxiety gets a bad rap in our modern world. We use it as a negative indicator. But Kierkegaard described it as the ‘dizziness of freedom’.
We back off from decisions because we take anxiety to be a signal of whether something is worth undertaking and if we can handle the ensuing challenges. Same for being ambivalent, for not being one hundred percent certain.
But anxiety is the other side of decision making. Decide comes from “cide” which literally means cutting off. Whichever path we take has consequences thus making us responsible for them.
Regret is also baked in for good measure regardless of which path we take. We can only physically inhabit one path out of the many available. Thus the paths not taken and their possibilities will always be an unknown.
The real question is which one we want to live with and are ok with in the long run.
5. Memento Mori
That's latin for “remember you shall die”. It’s what servants used to tell parading Roman Generals being feted. Covid perhaps was the ultimate crowd sourced reminder of this framework. The thought of death can be terrifying and equally clarifying.
Writing your obituary is a startlingly effective way to help avoid a corrosive feeling of regret that you did not take your life in new directions when you had the chance.
- Roman Krznaric, How to find meaningful work
Perhaps owing to the feeling of immortality that goes with younger age I never took these seriously.
These can come as a personal wakeup call or from the loss of a close friend. But we can proactively design this into our lives instead of waiting for fate to shake us out of stupor.
6. Bezos' regrets minimization framework
When I’m eighty, I want to have minimized the number of regrets that I have in my life, and most of our regrets are acts of omission, things we didn’t try, the path untraveled. Those are the things that haunt us.
- Jeff Bezos
If there is anything worth fearing in the world, it is living in such a way that gives one cause for regret in the end.
- A. C. Grayling
Regret is a powerful lens to look at our impending decision and its potential impact. Research has proven that the choices we didn’t make tend to loom larger with passing time.
7. Buridan’s ass
Put exactly midway between a stack of hay and a pail of water, Buridan’s ass died from hunger and thirst as it could not make up its mind.
Not making a choice is a choice in itself. The default has consequences, often hiding in plain sight. In conditions of uncertainty, imperfect action is better than perfect inaction.
8. There is no inner ring
Entire lives are spent chasing what CS Lewis calls the inner ring. We've been outsiders throughout and we want to be the insider, whether that's becoming the VP or a NY Times bestselling author.
And once inside we find another ring further inside. We are an outsider again. We would rather be anywhere but where we are today.
.. one of the most dominant elements is the desire to be inside the local Ring and the terror of being left outside.
The torture allotted to the Danaids ... that of attempting to fill sieves with water... is the very mark of a perverse desire that it seeks what is not to be had. The desire to be inside the invisible line illustrates this rule.
As long as you are governed by that desire you will never get what you want. You are trying to peel an onion: if you succeed there will be nothing left. Until you conquer the fear of being an outsider, an outsider you will remain.
If all you want is to be in the know, your pleasure will be short lived. The circle cannot have from within the charm it had from outside. By the very act of admitting you it has lost its magic.
You merely wanted to be “in.” And that is a pleasure that cannot last. As soon as your new associates have been staled to you by custom, you will be looking for another Ring. The rainbow’s end will still be ahead of you. The old ring will now be only the drab background for your endeavor to enter the new one.
— C S Lewis, Inner Ring
9. Bezos' reversible vs irreversible decisions
Some decisions are consequential and irreversible or nearly irreversible—one-way doors—and these decisions must be made methodically, carefully, slowly, with great deliberation and consultation. If you walk through and don’t like what you see on the other side, you can’t get back to where you were before. We can call these Type 1 decisions.
But most decisions aren’t like that—they are changeable, reversible—they’re two-way doors. If you’ve made a suboptimal Type 2 decision, you don’t have to live with the consequences for that long. You can reopen the door and go back through.
- Jeff Bezos
Is your decision reversible or irreversible?
10. We cannot outsource accountability
We want someone else to assure us of a safer tomorrow. We want to know how: how to do it, how much it costs, how long it will take, how to get those people to align with us, how to measure it, and who else is doing it.
All of this is a wish to go to heaven and not have to die. We want certainty before we act. As long as we wish for safety, we will have difficulty pursuing what matters.
- Peter Block, Answer to How is Yes
This is the promise of almost every online marketing scam: here's the answer, the hack, or the formula so you don't have to "waste" time trying to figure it out.
Often implicit, we want the upside but not the associated downside.
11. Time is not money
Why risk the things he had limited amounts of to increase the quantities of things he had unlimited amounts of?
- Manfred Kets de Vries, CEO Whisperer
Franklin's advice of time being money distorts how we see it. They are anything but the same. It's a false comparison. Because money can be quantified easily, we tend use it as a default measure. But money is infinite and replaceable whereas time aka our life is not. We only have a finite amount of time. So what are we really trading off?
12. Freedom and security don’t go together
Those who would give up essential liberty, to purchase a little temporary safety deserve neither liberty nor safety.
- Benjamin Franklin
George Monbiot in his essay Choose Life invokes Franklin’s framework of choosing liberty over security:
Whenever you are faced with a choice between liberty and security, choose liberty. Otherwise you will end up with neither. People who sell their souls for the promise of a secure job and a secure salary are spat out as soon as they become dispensable. The more loyal to an institution you are, the more exploitable, and ultimately expendable, you become.
- George Monbiot, Choose life
So many people live with unhappy circumstances and yet will not take the initiative to change their situation because they are conditioned to a life of security, conformity, and conservatism, all of which may appear to give one peace of mind, but in reality nothing is more damaging to the adventurous spirit within a man than a secure future.
13. Forget success and happiness
Don’t aim at success—the more you aim at it and make it a target, the more you are going to miss it. For success, like happiness, cannot be pursued; it must ensue and it only does so as the unintended side-effect of one’s dedication to a cause greater than oneself or as the by-product of one’s surrender to a person other than oneself.
Happiness must happen, and the same holds for success: you have to let it happen by not caring about it.
- Viktor Frankl
Obliquity can be more effective than directness when it comes to success and happiness. We are most happy when we are not chasing them directly.
14. Deciding is doing, not thinking
Then indecision brings its own delays, And days are lost lamenting o’er lost days. Are you in earnest?
Seize this very minute;
What you can do, or dream you can, begin it;
Boldness has genius, power and magic in it.
— Johann Wolfgang von Goethe
Thinking of important decisions can easily end up being a futile mental exercise on the road to nowhere. We often “decide” but don't take action. We forget that the real decision and choice is taking action in physical reality, not just mental rumination.
We are what we do.
- David Reynolds
Choices can muddle reality whereas actions clarify it. Decisions per se don’t generate feedback from the real world whereas actions do.
15. Ambitions have expiration dates
Whoever in middle age, attempts to realize the wishes and hopes of his early youth invariably deceives himself. Each ten years of a man’s life has its own fortunes, its own hopes, its own desires.
- Johann Wolfgang von Goethe
There’s a limited half-life to our intrinsic motivations and fires. It can take work and patience to bring them out. But too many of us are really good at drowning them. Do this long enough and over time the fire eventually dies out.
This is the key flaw in any early retirement movement - I will do it and "then". The "then" might be very different from what we have imagined today.
The projects that inspire you today might not do so 5 years from now or even a year from now. Humans are anything but static. What is more likely is losing interest and regretting you didn't take action earlier.
16. Gradatim Ferociter
Resist the temptation to start by making a big decision that will change everything in one fell swoop. Use a strategy of small wins, in which incremental gains lead you to more profound changes in the basic assumptions that define your work and life. Accept the crooked path.
The biggest mistake people make when trying to change careers is to delay taking the first step until they have settled on a destination.
- Herminia Ibarra
The trap is of “all or nothing thinking” where we want to make drastic changes overnight and discount the small actions and changes that eventually add up to a big change. An apt statement to counterbalance this tendency is Blue Origin’s latin motto “Gradatim Ferociter” — step by step, ferociously.
17. The right path doesn't exist, for now
Often we start off looking for a clear path. But for most worthwhile things in complex domains aka life, there is none. The path tends to emerge over time as we take action. Just like the escalator that doesn't start until we take the first step, so is often the case with our next project. It becomes clear only in hindsight.
18. Money is the cheapest
Money is only one measure but also the lowest form of value exchange. There are other higher forms — time, energy, and identity. Can you consider your decision in light of these?
Will you get your time back? Is the experience timeless? Does your work energize you? Who are you becoming(identity) in the process. More importantly do you like the person you are becoming?
19. Don't look for purpose. Create it.
This is the true joy in life, the being used for a purpose recognized by yourself as a mighty one; the being a force of nature instead of a feverish selfish little clod of ailments and grievances complaining that the world will not devote itself to making you happy.
- George Bernard Shaw in Man and Superman
Reminding ourselves of an overarching purpose can give some much needed perspective. If we don’t have one or haven’t figured it out yet, that’s a clue.
But the biggest mistake is to “look for” a purpose. This implies it lies elsewhere. Instead we have to “manufacture” our purpose and keep refining it.
20. Test the extremes to find the mean
Thinking of options in the extremes sheds better light on them. One example is fear.
In Aristotle’s list of vices and virtues, the virtue of courage sits in the middle of the vices of recklessness and cowardice. If fear is paralyzing us, looking at our decision from the extreme perspectives of recklessness and cowardice can yield different answers.
Where does your decision fall on that continuum? What would you do differently if you switched to the other extreme?
21. BENTO framework
The now matters. The future matters. The challenge and opportunity is to hold onto both at once.
- Yancey Strickler, founder of Kickstarter
Strickler has a decision making framework called BENTO - BEyond Near Term Orientation. Like the Japanese bento box, it’s a 2x2 matrix along the axes of self-interest and time. This creates the four boxes of Now me, Now us, Future me, and Future us.
The values of Now Me are security, pleasure, and autonomy whereas that of Future Me are mastery, purpose, and grit.
How can you approach it as an "and" instead of an "or"? Both present and future rather than present or future. Often we see it as a false dichotomy - one at the expense of the other.
22. Satisficing vs maximizing
The alternative to maximizing is to be a satisficer. To satisfice is to settle for something that is good enough and not worry about the possibility that there might be something better. A satisficer has criteria and standards. She searches until she finds an item that meets those standards, and at that point, she stops.
- Barry Schwartz in The Paradox of Choice
Choices often paralyze us because we are trying to optimize rather than satisfice. We don't want to "settle". But too many options also means we can never be sure what we pick is in fact the best. So we never make the choice which means ensuing indecision and inaction
Are we wanting our next choices to be perfect? Are we letting go of what might be possible for the fear of imperfection or making a mistake?
23. Risk and uncertainty are different
Risk can be minimized and mitigated whereas uncertainty is ever-present and cannot be eliminated. Have we set ourselves the impossible goal of eliminating uncertainty completely?
As humans, we are engaged in a perennial search for certainty, safety, and to feel secure against the backdrop of a world that is replete with uncertainties and unpredictability. We struggle continuously and fight against this reality, trying to eke out some semblance of meaning, some form of security, against which we can measure ourselves as constant and safe.
Paradoxically, searching for security in itself generates ‘existential anxiety’.
- Alison Strasser
Uncertainty is a given in any undertaking including the default one we're already on right now. The search for certainty where there isn’t any is a recipe for frustration and being stuck.
24. Forget planning, try crafting instead
Management guru Henry Mintzberg once contrasted what he called “planning” and “crafting” strategies. When we think of planning, he argued, we think of a person who “sits in an office formulating orderly courses of action derived from a systematic analysis that precedes implementation.”
Crafting is completely different, involving “not so much thinking and reason as involvement, a feeling of intimacy and harmony with the materials at hand, developed through long experience and commitment. Formulation and implementation merge into a fluid process of learning through which creative strategies evolve.”
— Herminia Ibarra, Working Identity
We want the perfect plan before we start. In contrast, approaching it as crafting where the plan emerges as we engage is a much more practical approach.
25. Objective risk vs subjective risk
Jim Koch of the Boston Beer Company uses the mountain climbing distinction of objective risk vs subjective risk. Too often we don't differentiate between the two.
An objective risk is something that can kill you. A subjective risk is something that just frightens you. The two are often extremely different, but, unfortunately, things that frighten you are often not the real dangers, and the real dangers are often things that don’t frighten you.
The objective risk was wasting years of my life stuck in something that appeared attractive but that I really didn’t enjoy. A lot of entrepreneurship and innovation seems perilous, but it’s not. And a lot of things that seem safe and comfortable are, in fact, profoundly risky.
— Jim Koch in Getting There
26. Don’t get hung up on the "how"
Confusion usually comes from focusing on process, or solution, and not being able to see where you are going. When you are considering what you want, your ability to focus your attention toward desired results eliminates this confusion.
When you are confused, it is usually not about where you want to go but how to get there.
- Seth Godin
We often get flummoxed because we don't know how or at least cannot imagine today how we would get to our desired goal. We get hung up on the how, the process.
But the more important question is "why", because the "how", the process can be figured out. There are many different hows whereas there might be only a few or just one why.
27. Pursuing what matters runs counter to culture
The only way to deal with an unfree world is to become so absolutely free that your very existence is an act of rebellion.
— Albert Camus, The Outsider
Living life on your terms can come with the downside of going against the herd. This goes against how we are biologically programmed.
Acting on what matters means that we will consistently find ourselves feeling like we are living on the margin of our institutions and our culture. This calls for some detachment from the mainstream.
The choice to not seek societal approval, parental pride, and institutional safety is a very difficult and personal matter. It may be possible to be ambitious and not lose control over our own lives while pursuing the ideals of another, but I have rarely seen it work.
- Peter Block, Answer to How is Yes
It's also worth examining our ambitions more closely to understand their source. Are they truly ours? Are we playing our own game or someone else’s?
28. Grace doesn't come cheap
When we zero in on cost too soon we constrain our capacity to act on certain values. There is no such thing as cheap grace. When we consider cost too early or make it the overriding concern, we dictate how our values will be acted upon because the high-cost choices are eliminated before we start. The dilemma is that we do not want to pay for our freedom.
- Peter Block
Often unknowingly, we want the upside but not necessarily the downside. Are we afraid of taking the next step because we think the “cost” of doing so is too much? Perhaps we are not as serious or as committed as we thought.
29. The safest choice can be the riskiest
The most common form of despair is not being who you are.
- Soren Kierkegaard
“What are the “riskiest” choices? Those that don’t allow you to become the person you want to be, to live your life full measure.
Survey results confirm that people’s biggest fear is neither death (ranks third) nor public speaking (second) but “failing to live a meaningful life.” That’s our greatest fear, our biggest risk. And it all begins with not living your life.
- Mark Albion
What we assume to be the safest choice from one perspective might be the riskiest when looked at from another.
30. Being vs "having" and "seeming"
The basic practical-moral problem in life is not what to do but what to be.
- John Shotter
Culture programs us to focus on having and seeming.We want to have certain things so we can seem a certain way. But who are we being in order to have and seem?
31. The four primary human drives
In Driven, the authors list four primary innate drives that dominate human thinking and shape our choices : the drive to acquire, the drive to bond, the drive to learn, and the drive to defend.
Our struggle with balancing careers and lives is often because one or more of these drives are going either unsatisfied or in direct conflict with each other.
We are often skewed towards one at the cost of the others.
32. Sunk costs can sink us
Faced with the choice between changing one’s mind and proving that there is no need to do so, almost everybody gets busy on the proof.
- John Kenneth Galbraith
We are naturally biased towards options that we've invested a lot of time and money into, aka the sunk cost fallacy. Are we overweighting what’s already been done and underweighting the possibilities of this other path?
33. Writing your version of the story
You know the business plan won’t survive its first encounters with reality. But the discipline of writing the plan forces you to think through some of the issues and to get sort of mentally comfortable in the space.
- Jeff Bezos
Humans are meaning-makers and meaning-seekers. We do this through the stories we tell ourselves. However they tend to be in the background and almost invisible.
One way to gain perspective is making them explicit by writing down our “situation”. Why bother?
To make distinct and coherent what is indistinct and incoherent right now. It creates physical separation from our thoughts. And makes us realize that our story is but one construction or interpretation amongst many possible ones.
34. Uncover hidden assumptions
Even though our basic assumptions often remain hidden from our conscious awareness, they nevertheless determine how we manage our careers. Too often we fail to question them, even if they are obsolete or wrong.
Precisely because they are taken for granted, basic assumptions are very hard to change. When they remain implicit, we only make incremental change. We only move from one situation into another that is superficially different.
- Herminia Ibarra in Working Identity
Implicit assumptions by their very makeup are hard to identify. But once made obvious they can loosen their grip on you and your decision making. These could be assumptions and notions about yourself, about others or a certain career path.
35. Try sensemaking instead of decision making
Sensemaking is a more practical approach than decision making when operating in complex domains with high uncertainty. Aka life.
Often they are not decisions per se. Rather we are trying to make sense of who we are, where we are, what we have, what that means, and so on.
We are feeling our way forward rather than choosing between clearly marked options. It's not classical decision making as many would have us think. It's more of wayfinding and less of navigating.
The best framework
I hope you found these mental models as useful as I did. Whatever framework we end up using, it's worth asking whether our particular approach increases or decreases our capacity for action. Whatever increases it is the best framework.
Does it stop us in our tracks or does it mobilize us? Does it create any movement? It can be easier to change direction when moving than at a standstill.
Are you moving?
You will dig The Managerial Mind on Mondays newsletter. It's free and every edition covers essential frameworks on leadership, careers, and organizations in bite sized form.
I have explored other aspects of careers in the below articles:
- Two critical questions when considering a midlife career change
- Common mistakes to avoid in mid career
- Challenges of transitioning from technical into management/leadership
- Oliver Burkeman's last piece in Guardian.
- Inner Ring by CS Lewis.
- Choose Life by George Monbiot.
- Aristotle’s virtues/vice
- Buridan's Ass
- Cynefin framework for decision making
- Four drives of human nature
- Sunk cost fallacy
- Amazon shareholder letters
- Working Identity by Herminia Ibarra.
- How to Find Fulfilling Work by Roman Kzarnic.
- Invent and Wander by Jeff Bezos, Walter Isaacson.
- Answer to How is Yes by Peter Block.
- CEO Whisperer by Manfred Kets de Vries.
- The Paradox of Choice by Barry Schwartz