Turning down a $60million pay package is hard to do.
It’s far easier when, like ex-Loom CTO Vinay Hiremath, you’ve already sold the company you co-founded and are wealthy enough to never have to work again. But it turns out that the harder part is grappling with identity, meaning and uncertainty when you have all the freedom in the world but no compelling reason to do anything.
This is what Vinay bravely and nakedly shares in his recent article “I am rich and have no idea what to do with my life”.
I’ve read it multiple times now, re-reading specific sentences over and over.
There are universal truths in there I’ve seen through my 22 years of coaching and in my own experience, so let’s zip through and pull out the gold.
1. Unless you know one thing, infinite freedom is the same as being stuck
Vinay had “infinite freedom”, but no compelling reason to do anything with it.
In a vacuum of desire and purpose where money and status used to be, everything felt secondary and unimportant. Just a side quest.
The missing element—and the only part of my coaching method that I insist everyone does because it’s so fundamental—is anchoring your personal values. These are the things in yourself, in others and out there in the world that matter most to you. They’re the building blocks, foundations and cornerstones for who you are. They pull at you. They whisper to you. They ring with truth.
When you don’t know your values you wake up each day in a vacuum of meaning and context that weighs heavy, creates stress, and takes from your sense of agency.
Your values are a constant guide, allowing you to look at the abundant choices and myriad paths in front of you and choose something that best honours what matters most.
2. Stop wasting energy on the appearance of control
Leaving where you’re at to “be alive again” is real Heroes Journey stuff.
As brave and compelling as it is, it also sets off every red flag there is.
Your brain will happily short-circuit your noblest aims to prioritise the need to be seen as having all the answers or even just having basic competence and self-efficacy. Even if it means you run yourself ragged or start behaving like a dick, there’s safety in having people see you as someone who has stuff figured out.
It means you won’t be judged, blamed or rejected for not having it figured out.
But the reality is that being hell bent on making sure everyone knows you have it all figured out doesn’t make you safe. It makes you stuck.
Don’t waste that energy.
3. Certainty is comfort and comfort is addictive
Your brain has two primary motivators: minimise danger and maximise reward.
These work like Robocop’s prime directives—base programming that drive you towards safety and certainty (reward) and away from anything risky or uncertain (danger).
When you’re without the certainty and purpose you’ve grown accustomed to—in a place that’s new, where the terrain is untrodden or everything feels uncertain—your brain will manufacture thoughts and use every dirty trick it can to turn you back towards safety and certainty.
Even at the cost of your happiness.
This is the reason for a lot of the crazy, sabotaging thoughts and behaviour you and I get up to, and the answer is surprisingly simple:
Normalise opportunity, defuse danger.
Remind yourself how far you’ve come, of everything you’ve learned and all the ways you’ve grown. Acknowledge that you’ve been in plenty of new and uncertain places and you’ve made it this far. You’ve built that capability.
Apply oodles of reassurance and bathe in compassion. Tell your brain “I know you want me to be safe and thanks for looking out for me, but we can figure this out and we’ll be okay, so here’s how we’re going to play it…”
4. Sooner or later you’ll catch up with the real you
Some people stay as busy as possible in an attempt to outrun pain.
Show me a serial goal-setter who never rests and always moves on to the next thing without ever really “feeling it”, and I’ll show you someone whose pain will eventually catch up with them in some spectacular ways.
Pain, hardship, trauma, grief, insecurity—whatever you “stuff down” is always just temporarily parked. It will leak out, block your progress and sometimes explode.
As I found when I was immobilised with grief in 2022, survival mode is a means of hunkering down for the short term to make sure you can get through, but survival mode is a short-term strategy and can never be a life choice.
One of the bravest things you will ever do in life is fully and wholeheartedly face yourself.
5. Expectations scramble your wiring
Expectations—of yourself, others, or what others expect of you—are a recipe for frustration and pain.
FMRI brain scans have shown that the circuits that deal with physical pain are the same circuits that fire when your expectations are dashed—it literally hurts when an expectation isn’t met.
Even with the promise of pain, our brains keep producing expectations in a flailing attempt to predict the future, creating layers of pressure and pulling you away from what matters.
And if you start tying your identity and ego to them, losing yourself is an inevitability.
Letting go of expectations clears the way for clarity and connection.
6. Drop your attachment to outcomes
Focusing too much on outcomes complicates everything. What if it doesn’t work? What if it’s not perfect? What if people see I’m not good enough?
Thoughts spiral with endless drama and “What if’s”, often at the cost of your success and wellbeing.
Instead, engage fully, adapt as needed, and rediscover the fun in simply playing the game.
7. Brutal self-honesty as a radical act of love
If you’re not being raw and real with yourself, what is it you’re doing?
If you’re not applying a healthy dose of humility—and I suggest a more fitting word here is compassion—to where you are and what you do, what are you doing instead?
The answer of course is denial, hiding, self-flagellation, sabotage, blind arrogance or simply just pretending.
The times I’ve lost myself have been when I’ve been avoiding that place of rawness and realness that allows me to take a meaningful and compassionate step forward.
Vinay’s wealth is an outlier but his struggles are universal
Vinay’s story may seem extraordinary, but the struggles he shares—uncertainty, identity, and meaning—are universal. Whether you’re struggling under the weight of expectations, navigating a major life transition, or feeling stuck despite wanting a more meaningful experience, the path forward begins with the courage to be “raw and real”.
