The Year I Couldn't Sleep
At the end of 2018, I put in my papers for premature retirement from the Navy. My exit date was December 2019.
The rules at the time required an officer to apply at least a year before the exit date, so that is what I did. From the day the application went in, I had a firm date and no job. I was still in uniform and still working, and I couldn't go out and look for what came next, because most corporate employers preferred people who could join immediately. I was a year away from being free to.
During that one year, I woke up in the middle of the night on numerous occasions, with my mind running through the same questions. What would I earn after the uniform came off? How long would my savings last? Would anyone hire me? Had I prepared enough? What would my family's life look like?
This was strange for a man who had spent twenty-three years in the Navy, much of it in submarines, and who had served as Chief Engineer of a nuclear attack submarine. I had been trained to handle emergencies inside a sealed steel hull under the sea. Yet it was a set of uncertain numbers that kept me awake.
That year taught me something I had never thought about. The problem was not the amount of money I had. The problem was my relationship with money. I had spent years learning my craft and almost no time learning what to do with what the craft pays.
What I mean by a relationship with money
I don't mean how much you earn or save. I mean how you think, feel and behave around money, usually without noticing.
Some people see money as security and hoard it. Some see it as a reward and spend it when it arrives. Some avoid looking at their accounts because the numbers frighten them. And some tie their sense of worth to their bank balance, so every fall in income feels like a fall in who they are.
Most of this is learned early, from how our parents talked about money and what we saw at home in good years and bad. It runs quietly in the background and shapes our decisions more than any financial product does. It sets our lifestyle, which is not just what we can afford but what we feel entitled to and what we fear giving up. It decides how we handle change. And it feeds our self-worth, which is why money trouble so rarely stays in the bank account. It spreads into sleep, health, marriage and confidence.
The plan that didn't go as per the plan
I did not sit and wait out that year. In mid-2019, I joined IIM Lucknow for a six-month business management certificate course. The thinking was simple. I was a technical officer moving into a corporate world, and I wanted to speak its language. The course would end around the time I left the Navy, and corporates would be coming to the campus towards the end of 2019 to hire. It was a sensible plan, and I felt better for having one.
Then the world changed. COVID began to cast its shadow, and by the time the campus drives were due, most corporates had frozen their hiring because of the uncertainty ahead. The offers I had been counting on simply did not come.
I want to be honest about how that felt. I had done everything right. I had applied on time, I had invested in learning, and I had a plan with a date on it. And none of it mattered, because the one thing I had not planned for was an event that no one in the world had planned for.
There is a lesson here that I learned in the Navy and relearned that winter. On a submarine, there are thousands of possible emergencies, and the crew trains for them for long hours. Yet the emergency that actually turns up is always a new one. The training is still worthwhile, because it keeps you sharp and calm for whatever comes. A financial plan is the same. It will not survive contact with reality in the form you wrote it. What you need is not a perfect plan but the habits, skills and reserves that let you adapt when the plan breaks.
The gap
I left the Navy in December 2019, as planned. The uniform came off, and what I had feared for twelve months was finally real. I had a year-old plan that had not worked, a course certificate, and no job.
Those weeks between December and the following March were the test of everything I had been thinking about. I no longer had the system around me. I had to look at every rupee of our expenses and decide what was essential and what was not. I had to have honest conversations at home. And I had to keep my head clear enough to keep applying, keep talking to people, and keep learning, even when every week brought news that made hiring look less likely.
What helped, to my surprise, was that the fear became more manageable once it was real. The nights of imagining the worst were harder than the days of dealing with it. When you are doing something, even something small, the mind has less room to run.
The call that changed things
By March 2020, I was lucky enough to get a consulting role with TCS, in product lifecycle management. I use the word lucky deliberately. I had prepared, I had worked at it, and I had put myself in the places where such a call could come. But I also know that in those weeks, with the whole country about to go into lockdown, many equally capable people did not get a call. The market was frozen, and I happened to get through at the right moment.
I think it is important to say both things. Preparation matters, and it is what puts you in a position to benefit when luck comes. But luck is real, and anyone who tells you their success was entirely their own doing is forgetting someone or something. I try to keep that humility, because it keeps me from judging people who have had less of it.
That role did something else too. It started my tryst with money and the markets.
My tryst with money and the markets
When you have just come through a period of real financial uncertainty, you stop treating money as a background subject. I had come out of the Navy with a pension and a family to look after, and I had just seen how quickly a plan could be thrown off course. I wanted to understand how money worked, how it could be made to work for me, and how to protect what I had.
So I began to learn, seriously, the way I had once learned engineering. I studied financial planning and qualified as a Certified Financial Planner. I started investing my own money and then trading, and I made mistakes along the way, some of them expensive. Today I run a content platform, and I write and teach about money.
None of this was part of the plan I had when I put in my papers at the end of 2018. That plan was to find a corporate job. What actually happened was that a closed door pushed me into a field I had never thought of entering, and that field gave me more independence than the job I was chasing would have.
I've come to think this is how it often works. The fear of that year was real, but it also forced me to build skills I would otherwise have postponed forever.
Everyone faces the cliff
Whatever profession we choose, we choose it so that, eventually, our needs are met and the people who depend on us are looked after. That makes money the one subject everybody ends up needing, and hardly any of us were taught it.
Officers who leave the services step out of a system that has looked after them completely. Housing, medical care, schooling for the children, a career ladder and a recognised identity all come bundled. On the day you leave, the bundle comes apart and you price every part of life separately for the first time. Money in service arrives on a fixed date in a predictable amount, so many of us reach our forties without having negotiated a fee, chased a payment, priced a risk or lived through a month with no income. The skills of leadership carry over very well. The skills of personal finance, for many of us, have simply never been used.
But this is not a military problem alone. The professional changing jobs in mid-career, the manager whose role is being restructured, the consultant whose contract may or may not be renewed next year, the founder whose salary has stopped before the business has started paying, the couple with a new child and suddenly higher expenses: all of them face the same uncertainty. What separates the ones who cope from the ones who don't is rarely intelligence or education. It is the quality of their relationship with money. Do they have a cushion? Do they know their own expenses? Do they have more than one way to earn? Do they believe, from experience, that they can find another income if one stops?
If the answers are yes, a shock is an inconvenience. If they are no, the same shock becomes a crisis. And the best time to build those answers is while you are still in the comfortable job, before you need them.
Making money and managing it are both skills
Here is the belief that changed how I think. There are a great many ways of making money in the world, provided you develop the skills for them.
We tend to assume that income is fixed by qualification. You trained as an engineer, so you earn as an engineer. But earning is really a collection of skills that can be learned: advising, teaching, writing, selling, negotiating, building, managing people, investing, running a small business. Each can be turned into income in more than one way. Someone with deep technical knowledge can consult, train or advise. Someone who understands numbers can manage money for themselves and for others.
My own path has gone this way. A naval engineer became a consultant, then a financial planner and distributor, then an investor and a writer. None of it came from a job description. It came from deciding to learn a skill, putting in the hours and being willing to start at the bottom of a new field.
There is a catch. Learning to earn without learning to manage is like filling a bucket with a hole in it. I have seen very high earners reach retirement with little because they never learned to keep and grow what they made, and modest earners build real security through discipline. You need both halves.
Independence is the real goal
When both skills are in place, you become independent. I don't mean rich. I mean that no single employer, client, contract or circumstance can take away your ability to look after yourself and your family. You can say no to a bad job or an unfair deal because you can afford to. A rough patch is something you plan around and not something you dread.
Think of how a ship is built. A well-designed vessel has redundancy: if one system fails, another takes over. A financial life needs the same. If all your income comes from one source, you have a single point of failure. With a pension, savings, investments, a skill you can sell and perhaps a second line of work, you can lose any one of them and keep sailing.
My own income today comes from several places, and I built that deliberately. It came slowly and it didn't come cheaply. But the calm it gives is very different from the nights I spent awake in 2019. That year, almost everything depended on one thing going right, a job offer at the end of a course. Today no single thing carries that much weight.
A few things I would do
I'll keep this short, because the details depend on your age, family and goals, and a qualified adviser is the right person to help with them. These are the foundations I wish I had laid earlier:
· Know your real numbers and what is enough for your family. Much money anxiety comes from fog, and a known problem is easier to carry than an unknown one.
· Build an emergency cushion and adequate insurance first. They buy you time to think, which is what bad decisions lack. A cushion would have made my gap months far calmer.
· Don't rest your future on a single plan. My plan depended on campus hiring in late 2019, and when that door closed, I was lucky that another opened. Better to have several doors in view.
· Keep learning one skill that could become a second income, and start before you need it.
Self-worth is not net worth
When I was losing sleep, part of what troubled me was a feeling that my value was tied to my rank and my income. In the Navy I held a position and a role. Outside, I would be starting again, and I wasn't sure what I would be worth in that new world.
What I learned is that the two are different, though they are easily confused. Net worth is a number on a statement and it will go up and down across your life. Self-worth rests on your skills, your character, your relationships and your ability to learn and adapt, and those travel with you into any job, city or stage of life.
A sound relationship with money keeps the two apart. When your finances are in order and you have skills you can rely on, a change of role or a dip in income doesn't threaten your sense of who you are. This matters just as much for our children as teaching them to save. A young person who grows up believing that worth equals wealth will spend a lifetime chasing and fearing. One who learns that money is a tool, and that skills and character are the real capital, will be far steadier.
What I would tell the officer of 2018
If I could speak to myself on the day I submitted that application, I would say a few things.
The fear you feel is normal, and it does not mean you are weak or unprepared. It means you care about the people who depend on you.
Your plan will probably not work the way you think. Make one anyway, because it gives you direction, but hold it lightly, and build your skills and reserves so that you can adapt when it changes.
The skills you have built in your career are worth more than you realise. The corporate world will not always see that at first, but it is true, and you will be able to apply them in places you have not yet imagined.
And start learning about money now, while the pay still arrives on the first of the month. I came to it after the shock. It would have been far gentler to come to it before.
Don't wait for certainty
If you are an officer approaching retirement, or a professional whose job feels less secure than it used to, start with small, practical steps. Write out the numbers, build the cushion, learn one new skill. And don't wait for certainty, because it doesn't come. In my years at sea, I learned that you plan carefully, you train hard, and then you act on the best information you have, adjusting as things change. Money works exactly the same way.
Final thoughts
All of us work, in the end, to look after ourselves and the people we love. That makes the way we think about and handle money one of the central subjects of our lives, and it deserves the same effort we gave to learning our professions.
My own journey took me from a submarine to a consulting desk, a planner's table and a trading screen, with some sleepless nights along the way. Looking back, I wouldn't skip those nights, because they pushed me to learn what I now try to share. Money, I have come to think, is not the goal. It is the means to a life with options, and the more skilled we get at making and managing it, the more options we have.
Master the skills of earning, and master the skills of managing. Do both, and you become what most of us are really looking for, which is independence: the ability to meet whatever comes with a steady mind.
Disclaimer: This article reflects personal views and experience for educational purposes only and is not investment or financial advice. Please consult a qualified financial planner or adviser for guidance on your own situation.