Questions and self-doubt on the journey to FIRE

“Stop working?”

“But what are you going to do? Will you find another job after a few years?”

“Do you have enough money?”

These are the most common reactions I get when I tell people that I am done with working and plan to retire early. By done, I mean really done, over it, forever. I have achieved financial independence and I don't intend to return to a full time job.

I turn 35 this year. And I have been thinking about calling it quits at my current job for a few months now. I have been planning for FIRE for a few years now and I was already very close to hitting my retirement number.

No, I didn't inherit a windfall. No, I didn't graduate debt free. No, I am not going to run out of money and survive on pet food when I am old.

“Then how did you do it?”

I worked hard and I didn’t get (too) distracted along the way. Over the years, I worked my way up into a high paying job. I consistently saved 50-70% of my income. I had a side hustle for a number of years, more than one side hustle in fact. I am deliberate about how I spend money and why I spend money.

Yes, I still live in the expensive city of San Francisco, but I plan to relocate in a couple of years to somewhere with a lower cost of living.

“You got lucky then”

No, there is a common misconception that you need millions of dollars in order to retire, or you will have to keep working your whole life. This myth is widespread because it is perpetuated by banks and insurance companies, the same institutions which are very much devoted to causing financial stress for people.

“Are you sure?”

Yes, you don't need to have millions of dollars to retire. You do however, need to pay off all your credit card debts as soon as possible, save more and spend less.

The magic number to FIRE is 25 times of your annual spending, so the more you save OR the less you spend, the faster you will reach this number. To dive into the maths, read my other post on ‘What is FIRE’.


“But work is so much fun, why wouldn't you want to keep working your entire life?”

Although I meant to be sarcastic, I know some people who genuinely enjoy their jobs and want to keep working forever. I am happy for them if they are working out of genuine enjoyment and not necessity to pay their bills.

I have enjoyed my work of course, I loved the work I do when I am working with smart, motivated individuals, who gets shit done. But I could have also easily become one of them zombie workers, who acts busy, attends endless meetings and then clocks out at 5pm. I guess I am way too restless to settle for that.

The point of reaching financial independence is not always to retire, but to have a choice. A choice to walk away when work starts to grind your soul down. A choice to take a break when you want to check a few trips off your bucket list. A choice to spend time with your aging parents or young kids. A choice to prioritise your physical and mental health over your company’s mission to change the world.

I think that life is much more than work. As I grow older, in addition to having spent more than 10 years working at really fast paced companies with high stress levels, this belief grows stronger by the day.

I am naturally a planner. Whenever my mind is idle, I dream about the future - the many possible paths I can go down and how life would be if I chose differently. The trouble is, when my mind barely has time to be idle in an all-consuming full-time job, I stop dreaming.

At some point, my body started protesting at the constant high stress levels, and broke down, twice. I went back to my company and asked for a six months sabbatical but was rejected. So much for all the HR fluff of caring for employees. I decided to bite the bullet and do it anyway.

During the sabbatical, which I now recognise as a mini-retirement, I had plenty of me time. Time to catch up on much needed sleep, to check many items off my bucket list and to travel to beautiful destinations.

During that time, I had the time and energy to dream again. When I projected my life into the future, no matter which path I chose, I couldn’t see a picture where I would be happily working in my 40s. That was when I decided that I needed to do whatever I can to get out of work and retire early.

“But you derail your career if you take a sabbatical”

Yea I definitely did, I gave up my so called hotshot career trajectory. But then again, there was no need to have that long term career path if my mind was set on financial independence. I just needed to get to my savings goal as quickly as I could.

Furthermore, I would probably have developed health complications if I stayed on in my job.  There comes a time, when faced with personal health issues, or treatment options for a loved one with health issues, when everyone has to ask themselves: is money or life more important?  

“What are you going to do with all this free time? Surely you will get bored?”

How about:

  • Spending time with aging parents, young children, and friends you hardly see due to long working hours

  • Travelling through _____ (insert exotic destination) for months at a time?

  • Indulging in creative work e.g. writing, painting, dancing, building - whatever got sucked out your soul when you had to do a 9 to 5

  • Reading all the books you always wanted to read

  • Binge-watching an entire TV series or binge-gaming the latest games whenever you feel like it

  • Taking an aimless afternoon stroll to nowhere in particular, just because

  • Achieving fitness goals because you now finally have energy and time to go to the gym instead of feeling exhausted at the end of every work day

  • Cooking healthier meals - no more binging on junk food or giving yourself a sinful treat to make up for the awful week at work

  • Learning a new skill through online courses

  • Volunteering at your local community to help the less fortunate

  • Consulting for people/small businesses who could benefit from your experience

  • Starting a small garden/farm to grow flowers and even healthier greens

Things expand to fill up available time. Finding interesting things to do is not an issue as long as you plan and provide structure to your daily routine and social needs. I plan to write more about this in the Happiness section of this blog later on.

Almost effortlessly, my six months sabbatical turned into a two year mini-retirement.

I was enjoying myself so much and I wished I didn't have to go back into a full time job. Unfortunately, at that time I had not reached my financial independence goals yet, and I needed to crush those numbers and build a little safety buffer by working for a couple more years.

This time round, I am really going to do it.

I look forward to “working on my retirement” full-time.

Do you have lots of self-doubt like me on your journey towards FIRE? Leave a comment below and tell me what keeps you up at night.