Anticipating Regret Led To Quitting My Job

I want to move out of the company.

I told my manager one morning in a quiet meeting room in the office.

I had been rehashing this moment in my mind for quite a while, but I had always held back, bogged down by thoughts like “The job is not what I want, but the schedule is tolerable, and I need the money”, “I don't want to go back to a startup”, and “I don't know if my side business will work out”.

Deep down, I knew I wanted to leave and start working full-time on my business, but the financial safety net of a full-time job and the risk of failure in running an online business kept me from taking the leap.

I endured months working on things that no longer brought me joy in an environment that was turning toxic and stressful by the day with no visible growth potential in my career.

Then, it happened. I quit.

In this blog post, I'll discuss how a simple mental framework helped me finally make a move on one of my most deferred decisions and how you can apply it to almost any decision-making in life.

Let's start with:

A backstory

A year before quitting my job, I had a one-to-one discussion with the same manager.

It didn't go well.

Work has been demotivating and stressful for a while, and I have been dreaming of leaving the job for a better one or pursuing something of my own, but I'd been holding on, hoping for better days, because the monthly paycheque was far too lucrative to give up.

That meeting is where it all came crashing down.

I left the meeting room feeling dejected, angry, and trapped in a place I desperately wanted to leave. The discussion made it evident that no matter how hard I try, I'll never live up to the company's unending expectations.

That meeting pushed me to the verge of resigning on the spot.

I didn't, though.

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That night, I tossed and turned on my bed, unable to sleep comfortably, and woke up groggy and helpless. It was one of the lowest moments of my life.

My life needed a change, and that is where:

Anticipating regret paved the way

That morning, after I woke up defeated, I went through what psychologists called anticipated regret, where you predict future regrets to make decisions that work in your favour.

I had been toying with the idea of going full-time on Hulry for years, but I always waited for the right time, such as when I had a financial surplus or when Hulry made enough to replace my salary, etc.

The allure of a predictable salary and the uncertainty of running a business kept me from taking on this project full-time.

But that morning, as I felt trapped in a job I no longer liked, helpless, unable to control my time, and stressed all the time, I returned to the prospect of moving full-time to Hulry, at least for some time, to give it a chance to bloom and become a sustainable business.

Although I could temporarily alleviate the problem by switching jobs and continuing to work on my business as a side hustle, it would not solve the problem. After a while, I will return to the same situation in the new company.

I had switched enough jobs in the past eight years to know this better by now.

Taking the leap and having a chance to work full-time on my business, though risky, was the most viable option for me.

I could work on something I loved on my schedule, not have to stress all day and not be driven by someone else's whims.

There was a problem, though — money.

I had savings, but not enough to waltz into the office the next day and quit my job.

But here's the thing:

This was the best time to take a risk and try something monumentally new in my career.

I had no debts, kids, or a housing mortgage, and I could operate with a low financial footprint by trimming down on some expenses.

That was when I realised that if I didn't take this risk now, I might not get another chance after I took on more family responsibilities, and I would regret it for the rest of my life.

Anticipating what I would regret a year or later helped me see things clearly and decide to take a chance on my business rather than staying at a dead-end job or jumping into another similar one.

Business aside, I knew I'd been delaying leaving the company for far too long, and if I had stayed there longer, I would have regretted my inability to act on this problem.

I had to quit the job.

Money was still a crucial factor, so I calculated my family's yearly expenses, added some buffer and projected the cost for a year of runway.

With the initial idea primed and ready, I pitched it to my wife. Both of us would have to be on board for this to happen.

She agreed on the spot.

She had been seeing me struggle for over a year and knew this would be a good chance for me to set up my business without getting burned out.

I spent that year building up the required capital and then quit my job to take a chance of a lifetime on this little project I've been nurturing for the past four years.

Regret is often seen as a negative emotion that brings one down. However, anticipating future regret helped me make one of my life's boldest and most deferred decisions.

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I'm yet to find out how this will work out, but I feel happy and relaxed working on something I have wanted to do for a long time.

I get pangs of stress from time to time because I'm still burning savings to fund my work, but it isn't as bad as the ones I got when working full-time at a corporation.


Work isn't the only place where anticipating regret has helped me make better decisions.

Another significant area where regret-driven decision-making has helped me is:

Taking back my health

Between working at my job and running Hulry on the side, my health took a back seat in the last two to three years.

I didn't feel any immediate critical repercussions, but my body felt fragile and rusted.

Backache and neck pain became regular ailments. Even basic movements, like lifting a bucket full of water, often led to muscle sprains.

I felt sluggish, heavy and uncomfortable all the time.

I tried making time for the gym regularly, but meetings and work knocked this activity off my calendar. I was not sick, so these minor problems seemed bearable and could be deferred later.

That is when it hit me.

My health was not a critical problem now, but it might be a year, two or even five years down the lane if I don't start taking care of my body.

Anticipating regret helped me prioritise my health.

After transitioning to working full-time on my business, I control my schedule entirely. Taking an hour out of my day to exercise at the gym was no longer a distant possibility.

That is what I do now.

While planning my weekly routine, I block out an hour every day around 4 pm to go to the gym and do strength training exercises.

I've never missed a day of planned gym sessions in the last three months.

Besides allocating time for exercising, I also made mindful changes in my diet.

I opted for a more balanced diet rather than a carbohydrate-rich or junk food option. I also reduced my sugar intake vastly. I still drink tea with sugar and enjoy the occasional sweets and desserts, but I watch my daily intake.

Diabetes is a common ailment in my family and among most of my friends. I'm fortunate not to be diabetic yet, and I want to keep it that way.

Taking steps now to prevent this condition while I still can is a much more viable and lucrative solution rather than gulping bottles of tablets five years from now.

Unsurprisingly, within a month of making these small changes in my routine and food, I started noticing changes in my body.

I felt energetic and lighter, and my back pain was gone. My body felt more fluid and ready for activities other than sitting in a chair and typing on my keyboard.

But anticipating regret doesn't only help us steer life-changing decisions, it also helps in:

Making tiny daily choices

I love my dog. For the past two and a half years, having him in our family has brought us more joy than we imagined.

Unfortunately, dogs' lifespans are not very long. I have a golden retriever whose average lifespan is around 12–14 years.

Being mindful of this ticking clock, I cherish every moment with him and aim to give him the attention he craves from me every day.

Sometimes, I feel too exhausted from work to play with him, but I muster some leftover energy to play with him or pet him when he comes over to me and slams his body by my side, asking for a belly rub.

I'll regret not enjoying and cherishing these moments when he's gone. As I wrote this, I got a bit teary-eyed and went and hugged him for a while.

You might not have a pet, but you might have a kid growing up faster than you can comprehend.

Anticipating regrets will help you be more generous with your time and attention and give your child the love they crave from you.

It'll only be a matter of time before they grow up and leave the nest. Cherish these priceless moments with them while you still have time.

Travelling is another area where visualising future regret has helped me savour different experiences.

My wife and I spend a bit extra money on good experiences, food, and souvenirs because we know that if we are too cost-conscious and deprive ourselves of these fine experiences, we will regret it after we're back home.

In an earlier blog post, I discussed how conscious spending can help you leverage money for a fulfilled life. Anticipated regret fits well with that concept, helping you pick things and experiences you really care about and will regret not having.

A good gauging question I ask in these situations where I'm still on the fence about a significant life decision or even the little ones is this:

Am I going to regret doing this or not doing this a year from now?

The answer clears a bit of the indecision fog and helps me evaluate things rationally.

Now, this way of thinking has generally helped me make decisions that were right for me and aligned with my guiding principles, but regret can be a double-edged sword.

So, to minimise cutting myself with regrets, I ensure that I:

Don't regret regretting

Anticipating regrets is one of my sharpest tools when I need to make a decision that could make or break my life.

But regretting too much can lead to a rabbit hole.

Understanding what I'll regret later comes from recalling past regrets. That is where the rabbit hole of regrets starts. What begins as an innocent exercise to gauge our future selves better spirals into loathing what we've done wrong in the past.

I avoid this by being mindful of what I'm regretting.

Am I regretting a potential outcome, or am I regretting what has already happened and can't be changed?

Feeling regrets over something in the future leaves room for changes and possibly avoiding that potential regret. Regretting over something that has already happened and can't be changed is only as valuable as the lesson we can extract from it and nothing more.

There's no value or happiness in digging up an old wound to feel worthless.

Anticipate potential regrets to decide better, but be mindful of when you stray from projecting a future self to beating up an old you.

Aim for the former.

Thanks for reading. Articles like this one take hours to write and publish. If you've found this article helpful, consider supporting my work by buying me some coffee.

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