Rakesh Shah sent me a message on a Tuesday evening — 11:23 PM, Toronto time. He’d just got home from work.
“Milind, I have given 18 years to IT. Good companies, decent money, no major complaints. But I sit at my desk every single day and I genuinely do not know why I am doing this anymore. I keep telling myself I want a change. I’ve been telling myself that for four years. Nothing moves. Is something wrong with me?”
I read it twice. A few days later, we got on a discovery call.
In the next 45 minutes, Rakesh described a life that looked completely fine from the outside — a senior role at a mid-size software company, a comfortable apartment in Toronto, a family he loved. And a private, growing sense of dread that somewhere along the way, he had built the wrong life.
He wasn’t burned out. He wasn’t depressed. He was successful and empty at the same time.
And he had no idea what he actually wanted instead.
When ‘I Don’t Know What I Want’ Is Not a Simple Problem
The first thing I told Rakesh — and the first thing I want to tell you — is that not knowing what you want at 43 is not a character flaw. It is not laziness. It is not ingratitude.
It is actually a very specific situation, and it has a very specific shape.
Most IT professionals I work with who arrive at this place have spent two decades being excellent at executing. They learned to solve problems that were given to them. They built careers around delivering what was asked — on time, under budget, with maximum efficiency.
What nobody told them is that finding what you want is a completely different skill. It requires a different kind of thinking. And if you have never practised it, of course you don’t know how to do it.
You are not confused because you are weak. You are confused because you were never trained for this question.
The Fire-Fighting Life and What It Costs You
Rakesh used an interesting phrase on that call. He said, “My whole career has been fire-fighting.”
I hear this constantly from IT professionals. Not just the workload — though the workload is real — but something deeper. When you spend every working day reacting, solving, responding, escalating, patching… your inner life goes quiet.
You stop hearing your own voice because the noise of urgent tasks drowns it out.
After a few years of this, when someone asks you — or you ask yourself — “What do I actually want?” you draw a blank. Not because the answer isn’t there. But because you have not listened inward for so long that you’ve lost the habit. And perhaps because, for a long time, it hasn’t even occurred to you that this might be a question worth asking.
I’ve worked with senior IT professionals across Bangalore, Mumbai, Toronto, and Dubai. What I see consistently is that this is not about the individual — it is about the environment. The constant urgency of tech work is designed, structurally, to take your attention outward. The problem is that clarity about your life only ever comes when attention goes inward.
Why the ‘I Should Know by Now’ Guilt Makes It Worse
There is a particular layer of suffering that comes with being in your early 40s and still feeling lost. It is the shame of it.
“I am 43. I have an MBA. I have a good salary. I should know what I want by now.”
This sentence — or some version of it — is in the heads of nearly every high-achieving professional I coach who is going through this. And it is the sentence that makes everything harder.
Because the moment you decide you should already have the answer, you stop actually looking for it. You start performing certainty you don’t feel. You tell people at dinner parties that you’re “exploring options.” You build a LinkedIn profile for a pivot you haven’t fully committed to. You look busy deciding while quietly avoiding the real question.
I know this from the inside.
It was February 2007. I was managing a branch of a successful ad agency — around 40 people reporting to me, good salary, good perks, a challenging role. The year before, the management had promoted me above my own boss. From the outside, it looked like I had everything.
But the glamour of a fancy designation and a corner office wears off quickly. My stress levels had gone through the roof. So I did something I’d never done before — I took a solo trip to Kerala. Just me, 48 hours, and that one uncomfortable question: what do I actually want? Not just in my career, but in my life. What is my life worth? How do I want to spend the rest of it?
The answers didn’t come easily. But somewhere on the upper berth of the train home, something shifted. I realised that despite everything I’d achieved since graduating from IIM Bangalore, I had not experienced the kind of peace I’d been quietly craving. That solo trip was the first time I’d felt genuinely free in years. And it was the beginning of everything that came next.
The Real Question Under the Question
“I don’t know what I want” almost never means what it appears to mean.
In my experience — 13 years, over 8,000 coaching hours, hundreds of clients in exactly this situation — “I don’t know what I want” usually means one of three things:
One: You do know, but it scares you.
It might mean leaving a career you’ve spent nearly two decades building. It might mean disappointing your parents, your spouse, or your own earlier ambitions. So you choose not to know. The not-knowing feels safer than the knowing.
Two: You have been living someone else’s definition of a good life.
Engineering. IT. A big company. A foreign posting. These were not necessarily your choices — they were the choices that made sense given where you came from, what your family expected, what the economy offered. They were rational. They were responsible. They just weren’t entirely yours.
Three: You have outgrown this chapter but have not yet written the next one.
You are not confused about your past. You are standing at the end of one chapter with a blank page in front of you. And blank pages are terrifying, especially for people who have spent their careers solving problems that already had a shape.
With Rakesh, after a few sessions, it turned out to be a combination of all three.
There’s something I often share with clients at this point. The brain is wired to be suspicious — it’s a survival mechanism. We almost always prefer a predictable bad over an unpredictable good. That’s why “I don’t know” feels so frightening, when in reality it is simply a space of nothingness waiting to be filled with something meaningful. Zen philosophy actually considers “I don’t know” a high state of being. The tragedy is that our education system and our workplaces reward knowing — they have no language for not knowing. So we learn to be ashamed of it, when we should be curious about it.
What Courage Actually Looks Like Here
Rakesh told me early on: “I want a career change but I lack the courage.”
I pushed back on the word courage. Not because courage is wrong — but because most people misunderstand what courage means at this stage of life.
They imagine courage is the dramatic leap. The resignation letter. The big announcement. The pivot that everyone can see.
But the courage that actually matters here is much quieter. It is the courage to sit still with an uncomfortable question and not immediately reach for a distraction. It is the courage to say, out loud, “I don’t actually know what I want” — to a
coach, to a trusted friend, or just to yourself at 11 PM on a Tuesday night.
It is the courage to take your own confusion seriously instead of dismissing it as a mid-life cliché.
That is not a small thing. Most people never do it.
A Note for Indian and NRI Professionals
There is a particular version of this struggle that I see almost exclusively in Indian and NRI professionals, and I want to name it directly.
Many of us built our careers under enormous family pressure and societal expectation. Engineering was not a choice — it was the obvious path. The job at a big IT company was not a passion — it was proof. The posting in Toronto or Dubai was not a dream — it was a duty to parents who sacrificed everything.
When you have carried that weight for 18 years, asking yourself “what do I actually want?” can feel almost offensive. Who are you to want things, when so much was given up for you?
But here’s what I’ve come to believe, after sitting with hundreds of professionals in this exact situation: your parents didn’t sacrifice so you could be miserable in a well-paying job. They sacrificed so you could have choices. Choosing — really choosing — is not ingratitude. It is the whole point.
Where to Start When You Don’t Know Where to Start
I am not going to give you a five-step framework. You have read enough of those.
What I will tell you is what I told Rakesh: start with subtraction, not addition.
Instead of asking “what do I want?” — which is too open, too vast, and tends to produce more anxiety than insight — start with: “What am I doing right now that feels genuinely wrong?”
Not what is difficult. Not what is stressful. Those are often things worth keeping. What feels fundamentally misaligned with who you are? What feels missing from your life?
For Rakesh, the answer came quickly: he didn’t hate the work. He hated the invisibility of it. After 18 years, he felt like a cog — technically excellent, personally irrelevant. What he wanted, when he finally got honest about it, was work where his specific way of seeing problems mattered. Where he was not just a resource.
That one insight changed the direction of his entire search. The question stopped being “what industry should I move into?” and became “what kind of work environment values what I specifically bring?”
Those are very different questions. And the second one has answers.
What I Learned When I Was in the Same Place
In 2009, I told my wife Seema that I wanted to leave my corporate career and go out on my own. She was understandably taken aback. She asked what I planned to do for a living. I told her I wanted to empower people. She asked how. I said I had no idea.
I don’t know how she felt in that moment. But I know exactly how I felt: scared. I wasn’t sure I’d succeed. I wasn’t sure the income I’d generate could come anywhere near my VP-level salary. And underneath all of that was the quieter, more embarrassing fear — what would people think if it didn’t work out?
Eventually, I decided to go beyond that fear and simply embrace the not-knowing. I was about to step off one train and board another — without knowing where it was headed.
How I wish someone had told me then that it was never going to be about the destination. Or even about the journey, really. How I wish someone had told me it was going to be about who I was destined to become along the way.
That is what I try to tell the people I work with now. The confusion you are sitting in is not the problem. It is the beginning of the answer.
If this article found you at 11 PM on a Tuesday — or during some other quiet moment when a question you’ve been avoiding finally got loud — I want you to know something. The confusion you feel is not a dead end. It is a beginning.
I work with corporate professionals, mid-career, who are done pretending they have it figured out and are ready to finally ask the real question. If that’s you, you can reach me at
milindjadhav.com.
About the Author
Milind Jadhav is a certified life coach based in Pune, India, and one of the pioneers of professional life coaching in the country. Since 2012, he has worked with 450+ clients across India, the Middle East, Europe, and North America — primarily corporate professionals navigating career transitions, burnout, and the bigger questions that don’t fit into a performance review. He holds a Post Graduate Diploma from IIM Bangalore and has logged 8,000+ hours of individual coaching. He can be found at milindjadhav.com.
If this article has resonated with you and you’d like to explore coaching, you can book a free introductory call with me.
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Frequently Asked Questions
Why do I feel lost in my career after so many years of success in IT?
Career confusion after a long stretch of success is more common than most people admit. IT work demands constant outward focus — solving problems, meeting deadlines, delivering results — which leaves little space for the inward reflection needed to stay connected to what you actually want. After 15 to 20 years, all the external markers of success (title, salary, company name) can be firmly in place while the inner sense of meaning quietly fades. This is not a personal failure. It is a signal worth taking seriously.
Is it too late to change careers at 43?
No. Some of the most successful and satisfying career transitions I have witnessed in my practice happened in the early to mid-forties. You have something a 25-year-old doesn’t: two decades of self-knowledge, industry understanding, and accumulated skills that transfer in ways you may not immediately see. The transition requires honesty, patience, and the willingness to move before you have the complete picture. But it is not only possible — for many people, it is exactly the right time.
How do I figure out what I want when I genuinely don’t know?
Start with subtraction rather than addition. Instead of trying to identify a passion or a dream from scratch, ask yourself what aspects of your current work feel fundamentally wrong — not just stressful, but misaligned with who you are. Clarity usually comes in small steps, not sudden revelations. A good coach, a trusted friend who will be honest with you, or even a private journal can help surface what you already know but haven’t let yourself hear.
What is the difference between burnout and career confusion?
Burnout is primarily about energy depletion — you are exhausted, cynical, and struggling to function. Career confusion is different. You may have energy, you may even perform well at work, but you carry a growing sense that you are doing the right things in the wrong life. Both deserve attention. Career confusion without burnout is often easier to address — but it is also easier to ignore, which is why so many professionals spend years deferring the question.
Do I need to leave my job to find clarity?
Not necessarily — and certainly not at the beginning. Clarity comes from honest inquiry, not from dramatic action. Many professionals I work with find significant direction while still employed, and that financial stability actually helps. Impulsive exits rarely produce the insight people hope they will. What produces insight is intentional reflection, honest conversation, and the willingness to sit with uncertainty long enough for something real to emerge.
