My Ten-Year Path to Making Work Optional

I came to the United States about ten years ago with less than $5,000 to my name. This year I left my job to build things, and I could do it because I no longer needed the paycheck.

Nothing about that path was exotic. There was no startup exit and no inheritance. There was a normal corporate job, a habit of saving about half of what I earned, and a long, often embarrassing education in investing. What I think mattered most was the order I did things in.

1. Year oneBuild the cash cushion
2. $100Begin investing carefully
3. Years two to nineLearn through small mistakes
4. By year nineInvestment income compares well with salary
5. Year tenLeave to build

Year one: save half, build the cushion, take no risk

My first salary in the US was about $80,000, which came to roughly $4,500 a month after taxes and deductions. I lived in Cincinnati, where rent, food, shopping, and utilities came to $2,000 to $2,500 a month. I saved almost half of my take-home pay.

That was easier for me than it sounds. I was single. I did not drive, and I lived close enough to work to walk, so there was no car payment. I had no student loans. As a new immigrant fresh off the boat, living on $2,500 a month felt like being on top of the world.

I had one goal for that money: an emergency fund. I believed that if I ever wanted to take a risk in life, I first needed a foundation that a bad month could not knock over. So for the first full year I put every dollar I could into the bank’s savings account and earned whatever a savings account paid a decade ago, which was not much.

I did not invest anything that year. I knew almost nothing about investing except that it looked like gambling. Some people seemed to make money at it, and many more seemed to lose. I was in no hurry to join either group.

Today I still hold about a year of expenses in cash, though it now sits in a Treasury bill fund rather than a savings account. The habit is the same one I started in Cincinnati.

The $100 test

Once the emergency fund was full, after roughly a year, a friend invited me to join Robinhood. I put in $100.

Not $1,000. One hundred dollars was the most I could justify losing on what I still considered an expensive hobby. I had lived in India on less than $500 a month, so spending $100 on something that might vanish felt outrageous. Perspective.

The idea of putting in $1,000 kept me up at night, and that told me something precise: my risk tolerance was extremely low. I decided I would only do things I could live with if they went the other way.

That rule has not changed in ten years. I take calculated risks, where I know in advance how much I am willing to lose if the thesis is wrong. My measure is not a formula. It is whether a position will make me sweat or lose sleep. Another way to put it: if losing the money would change your lifestyle, the risk is too big.

Nine years of learning the hard way

With the cushion in place, I started investing more seriously. I read, I watched videos, and I picked up the basic concepts. I stuck to big companies whose products I used myself, which kept me out of the worst trouble. YouTube tried hard to talk me into specific stocks, and I resisted most of the time.

Many investors go through that cycle, and I was no exception.

Closing that gap took years of reading and a lot of small losses. My first options trades were part of the same education. If I had skipped the emergency fund and started here, those losses would have been coming out of rent money, and I doubt I would have stayed in the market long enough to learn anything.

The number that told me work was optional

About nine years into the journey, I noticed something while filing my taxes: my investment income had been doing comfortably well relative to my job salary for a couple of years.

I had been tracking every expense for a decade, and I kept the same kind of records for my trades. So I could check the claim properly instead of trusting a feeling.

I also checked whether the result survived a narrower test. I looked only at the portion of my trades where I was using the wheel: selling cash-secured puts on stocks I wanted to own, followed by covered calls if I ended up holding the shares. That income alone had covered my expenses for many quarters in a row.

That approach is often called the wheel. It has real risks. The stock you agreed to buy can fall well below your strike price, and the shares you own can be called away below where they later trade. It is not a paycheck, and it is not what I would tell anyone else to depend on. What mattered to me was that my records showed it had covered my expenses across many quarters, with position sizes I could sleep through. If you want the mechanics first, I have explained how an options contract works separately.

My wife and I talked it through. If the time ever came, we agreed, we would be fine. I was proud of that conversation. It was the milestone.

And then I kept working.

Being able to replace my salary was not a reason to leave it.

The reason came from somewhere else

Early this year I started building with agentic AI. Ideas that had lived for years in a Google Sheet suddenly looked within reach. Using Claude Code, I built an analytics Slack bot that anyone at the company could use to get analysis done. I built it by myself.

I was proud of the bot. What struck me more was that I kept staying up late to learn and build with these tools. It felt like a magic wand, and I wanted to master it. The rest of my job, the part that was not building, stopped holding my attention. That went on for months.

My wife and I had the conversation a second time and agreed it was the right move. So I left the job to build things.

Will it succeed? Who knows. Will I learn and have fun doing it? Hell yes.

Before I gave notice, I set aside a year of expenses in SGOV, a short-term Treasury bill fund, so that nothing I build has to make money on a deadline. My mornings go to actively managing the investment portfolio. The rest of the day goes to building. There are no deadlines set by someone else, and I have already learned that my spending did not stay where the spreadsheet said it would. That is fine. The cushion was built for exactly that.

The order, if you want to steal it

1. Build the cushion first. A year of saving felt slow, but it made every later mistake survivable.
2. Let sleep determine your position size. Start with an amount whose loss would annoy you without changing your life. Grow it only while that remains true.
3. Keep the tuition affordable. Expect to be bad at investing for years, and keep every position small enough that you can stay around to learn.
4. Trust records over feelings. Tracking my expenses and trades let me see when work had actually become optional.
5. Treat optionality as permission, not a command. I reached it and kept working for another year. Leave because you have something worth running toward.

The useful question is not only how much risk would let you sleep at night. It is what you want that safety to let you run toward.