Big Career Decisions
Quiet help for choices you cannot quietly undo
There are decisions that you can smooth over later: a project, a committee, a short-term role. Then there are decisions that redraw the next decade: taking a promotion that rewrites your days, leaving a firm that shaped you, uprooting a family for a new city, walking away from a profession you gave your twenties to, committing to yet another degree or designation.
Those are the decisions this page is about
You probably already know the feeling. On paper, the opportunity looks rational. The compensation makes sense. The role aligns with what people expected you to want. The “sensible” move is clear. Yet somewhere under the analysis, something in you is uneasy. Not melodramatic panic. A steady, low-grade disquiet.
You are capable of thinking hard about markets, risk and capital. You model uncertainty for a living. Yet the closer a career decision gets to your own life, the harder clear thinking becomes. Loyalty, fatigue, guilt, envy, family expectations, sunk cost and fear of future regret all walk into the room at once. The spreadsheet loses its authority.
This is the terrain of Big Career Decisions.
Decisions that do not rewind cleanly
The questions that usually arrive here sound deceptively simple:
Do I stay or leave this firm?
Do I take this promotion or decline?
Do I move to another city or honour the life I have built here?
Do I go independent or remain inside a large institution?
Do I commit to another degree or stop collecting letters?
Each of those questions hides a cluster of others.
Leaving a firm rarely means just “resigning.” It means walking away from a reputation you built slowly, colleagues who have become friends, a language of in-jokes and shortcuts, and a version of yourself that has grown around that culture. Staying means something just as real: accepting a further stretch of the same patterns, the same politics, the same limitations, in exchange for familiarity, security and status.
A promotion is rarely just “more responsibility.” It can mean stepping further away from the work you love and deeper into the work you tolerate; shifting from substance to optics; moving closer to the blast radius when something breaks. Declining can feel like a betrayal of the younger self who thought this was the prize, or of the family members who brag about your title to their friends.
A move to another city is never just a change of skyline. It alters your daily air, your social fabric, your sense of safety, your proximity to ageing parents or growing children, and the way you feel walking down a street at night. A bigger role in a bigger market can also mean a smaller life.
Going independent holds genuine upside: control, focus, ownership. It also carries the very real possibility of isolation, cashflow anxiety and the quiet toll of always being “on.” Staying employed carries its own tax: compromise, bureaucracy, the sense of always working inside someone else’s story.
Another degree or designation can be a key that opens real doors. It can also be the most respectable way to avoid a harder move: naming that the role, firm or profession no longer fits. You know all of this, and still the choice is not obvious.
These decisions are expensive to reverse. They deserve more than a hurried pros-and-cons list scribbled after midnight.
The quiet violence of staying by default
One of the most common patterns I see is not dramatic quitting. It is extended drifting.
You promise yourself that you will make a decision “after bonus,” “after this transaction,” “after the next board meeting,” “after the children finish this school year.” Each delay is reasonable in isolation. Together they form a new kind of decision: to keep living someone else’s plan because changing course feels disloyal, risky or selfish.
Meanwhile, the job hardens into identity. You become “the person who could have left but stayed.” The outside world sees stability. Inside, you know that fear, habit and obligation are doing more of the steering than conviction.
The same thing happens in relationships. Many intelligent professionals stay in decent but unsuitable partnerships because leaving feels cruel, or because the thought of re-entering the dating world at mid-career feels unbearable. The result is a polite stalemate where both people quietly shrink.
The paradox is that the kindest choice in the long run can feel heartless in the short run. Walking away from a role or relationship that no longer fits may leave colleagues and family disappointed, angry or baffled. For a time, you might be the villain in someone else’s story. People pleasers, especially, find this almost unbearable.
Staying to protect your reputation as “nice” or “loyal” has a cost that compounds silently: resentment, numbness, a slow erosion of self-respect. You pay that cost whether you acknowledge it or not.
Quitting without self-betrayal
Quitting a job, a city or a professional path is not automatically brave or wise. Sometimes the urge to leave is just burnout in disguise, or a fantasy that the next role will finally deliver the peace that no external change can guarantee. Sometimes the “new opportunity” is simply a slightly different cage.
The question is not “Should I quit?” The sharper question is:
What am I really trying to move away from, and what am I hoping to move toward?
When you look closely, three traps show up often.
The first is moral camouflage. You tell yourself you are staying for the team, for the clients, for your family, when the deeper truth is that you are staying because uncertainty terrifies you and the current role gives you something solid to say at dinner parties. Everyone applauds your loyalty while your inner life quietly thins out.
The second is image management. You worry about how a move will look on your CV, what your peers will say, whether your parents will understand, what LinkedIn will think. You start running public relations for a life that no longer feels like your own.
The third is perfectionism in disguise. You wait for a decision that carries no risk of regret, no possibility of loss, no chance of appearing foolish. That decision never comes. So you carry on, “sensibly,” while another year vanishes.
To quit without self-betrayal, you need a different standard: not “Will everyone approve?” but “Can I look back, ten years from now, and recognise this as a choice that honoured who I was then, with what I knew then?”
That is a higher bar and a kinder one.
How our conversations help
I cannot make your decisions for you, and you would not trust anyone who offered to. What I offer is a private, steady place to do the kind of thinking you rarely get to do alone, with someone who understands both the technical and human sides of your world.
We begin with where you actually are. Not the role description, not the LinkedIn headline, not the story your firm tells about you. The lived reality: how your days feel, what your body has been trying to say, where the cracks are at home, how you sleep, what you dread, what you remember enjoying and have quietly abandoned.
From there, we look back at how you have made big decisions so far. Many people discover a chain of choices driven by drift, duty, luck and the path of least resistance. Understanding that pattern does not invalidate the life you have built. It simply stops the pattern from running unexamined into your future.
Then we map scenarios with more honesty than most workplaces allow.
What happens if you stay for five more years? Not just financially, but to your health, your family, your imagination. What happens if you leave now? What would you actually be doing, day by day, six months in? What risks are you overstating because of fear, and what risks are you understating because of habit or pride? Where does loyalty serve you and others, and where has loyalty become an excuse?
This is not spreadsheet theatre. It is quiet scenario work for a high-stakes human decision.
We pay close attention to suitability: not just whether you can perform a role, but whether the pace, culture, politics, city, colleagues and clients are compatible with the person you are now, not the person you were when you chose this path. We notice how often you censor yourself in meetings. We notice which conversations leave you energised and which leave you feeling hollow. Those are data, too.
Importantly, we do not stop at insight. Each conversation ends with some small movement: a candid question you want to ask; a boundary you want to test; an informational conversation you have been avoiding; a draft resignation email you write and keep in a drawer; a quiet exploration of another city or sector without broadcasting your restlessness to the world.
Big career decisions rarely hinge on one dramatic moment. They are usually the result of many small, serious steps taken in the same direction.
Who this is for
Big Career Decisions is not a general career service. It is for a particular kind of person.
You tend to be intensely educated: an honours degree at minimum, often a master’s, plus a demanding designation. You work under professional codes where errors matter and ethics are not optional. Your daily work touches capital, pensions, infrastructure, insurance, corporate risk or similar territories where abstract choices land on real people.
You are introverted, or at least not sustained by constant visibility. You can perform when necessary, but you do not want a life built on performance. You would rather be effective than famous.
You are somewhere in mid-career or beyond. You have enough history to know that time is not infinite, and enough responsibility to know that your choices affect more than yourself.
You are not looking for slogans. You want someone who can sit with the full complexity of your situation, carry some of the weight of thinking with you, and help you decide in a way that leaves your conscience intact.
If you are standing on the edge of a choice
If you are circling a big decision, you probably already feel the tension: loyalty and fatigue pulling one way, curiosity and unease pulling another. Friends and colleagues offer advice coloured by their own fears and interests. Family members have hopes that are real and not always compatible with yours. Social media supplies a constant stream of examples that make every option look simultaneously glamorous and fraught.
In that noise, it is easy to forget a simple truth: staying is also a decision. Drifting is also a decision. Declining change is also a statement about what you believe your remaining years are for.
Big Career Decisions is the part of my practice where we treat those choices with the seriousness they deserve, without drama and without rush. Quietly, over a series of conversations, we work toward decisions you can live with and look back on without flinching.
Not perfect decisions. Suitable ones.