What I wish I knew before quitting my job

A while ago, I left my job as a trainee patent attorney to pursue a career as a software engineer. While I enjoyed the novelty of reading new inventions and developing literary skill in arguing against examiners, my hobby of many years, programming, was too hard to ignore.

Change is never easy and one involving your career even more so- my experience was no different, particularly given I’d never done it before.

As with many things, there are things you would have done differently. Hindsight is, as they say 20/20. Decisions that may not have shortened the journey but at least made it a little more comfortable.

If you hadn’t guessed by reading the title, this is what I’m going to share with you today. For the courageous contemplating their own change, these learnings may provide some guidance along the way.

Take your time- don’t rush

The urge to quit your job can be strong and sudden. You may be sick of the work, tired of the toxic culture, or just want a change.

But your first goal is to make sure whether these feelings are real and worth acting on. We all get down days or even down weeks.

This can be especially true if you just joined the company. Starting any job is overwhelming- in the whirlwind of new work, co-workers and location, it’s hard to see the forest from the trees.

I distinctly remember joining my first meeting. I felt like I had made a terrible choice of career. My co-workers were dripping with knowledge and all I wanted to do was head straight for the exit.

But the best thing to do at this time is to wait. Great haste makes great waste. Let the dust settle so you can lead with your head and not your heart.

If you start to feel comfortable after a few months, then great.

But if the feelings of dread, depression and despair surrounding your career persist beyond this, then it’s time to start planning what to do next.

Follow your curiosity

I’d been working for nearly half a year now. Every day, I would brave the daily commute reassuring myself that today would be different. That I was a new hire so of course I wasn’t expected to get this stuff straight away.

But when I looked around the office and I saw patent lawyers discussing the latest legal news with intrigue, attending lectures to learn more and present their learnings of new cases, it was obvious I was in the wrong place.

The truth is that deep down, I didn’t have any curiosity about patent law. I had no motivation to become better because I didn’t find any joy from the subject matter, nor did I desire the position that hard work would bring.

My manager was making 8 figures a year. Yet, I didn’t envy his position in the slightest. Moxie Marlinspike says:

As a young person, though, I think the best thing you can do is to ignore all of that and simply observe the older people working there.

They are the future you. Do not think that you will be substantially different. Look carefully at how they spend their time at work and outside of work, because this is also almost certainly how your life will look. It sounds obvious, but it’s amazing how often young people imagine a different projection for themselves.

Look at the real people, and you’ll see the honest future for yourself.

The cynical amongst us may say that work is not meant to be liked and that you should save your hobbies for your free time. I thought exactly the same before starting my first job. But now, I strongly disagree.

The truth is that the way to become valuable is to become great at one thing or good at a few things. And becoming good or great at something requires hard work. Becoming good or great at something which you have no desire to learn is like climbing Everest with lead strapped to you. You may reach the summit but boy will the journey be uncomfortable. And it may just break you before you get there.

It meant that in patent law, I would always be doomed to mediocrity.

In the words of Tony Fadell, a much wiser question to ask yourself is: what do you want to learn?

For me, all I could think about was programming. I would devour books and blog articles on technology on the train to work and retreat to the library on the dot of five. I would embed REPLs into Notion and play around with new language features during lunch time. And I was eager to follow in the footsteps of the great programmers of our generation.

Looking back, it was so painfully obvious that this is what I wanted to learn and devote time to that it seems odd why I didn’t see it earlier. I think part of it stems from the illogical way I’d been conditioned to view work and fun- work is meant to be a grind. Fun is something you do after work. Patent law to me felt like a grind. Programming felt like fun.

But 8 hours a day, 35 hours a week, 2080 hours in a year is a long time to be doing something you don’t like. It also represents a colossal waste of time- time in which you could spend getting paid to learn, in a field which you have a large amount of curiosity for.

So before I decided to leave, I asked myself two questions:

1. What do I want to learn?
2. Do I envy my boss’ position? If I were to magically reach the top of this field, would I be proud of my knowledge?

And I answered honestly.

The rest as they say is history.

We’re often told to have resilience. To battle on when the going gets tough. But this applies when you seek the goal before the effort.

Get advice (but not too much and from the right people)

By now, I felt sure that I wanted to change careers. And that technology is where I wanted to head.

But despite all the signs, there was still a niggling feel that I was about to make a huge mistake. I’d worked so hard to get here. Endured long interview processes, handled tons of rejection by other firms, and battled to build my resume.

So I sought advice from people close to me. I scrolled internet forums looking for people in my position, trying to find confirmation that what I was about to do was right. I read books hoping for clear direction.

And what I did I learn from all this?

I learnt that most advice is unintentionally terrible.

The reason is that you’re seeking advice for your unique circumstance. Yet, most people will advise you through their own experience.

Ask someone who’s been through financial difficulty- they’ll advise you to stay put. Work is for money they’ll say. Become financially independent. Then do what you’re interested in.

Ask someone who’s never had any responsibility- they’ll tell you to leave immediately and be happy (whatever that means).

Ask your parents- they may advise against it because they’re invested in protecting you and don’t want to expose you to unnecessary risk.

The point of this is not to never ask for advice. It showed me that the best advice comes from those who’ve stood where you stand and is specific to you.

For example, many people told me to only quit when I had another job lined up. But as a recent graduate with no dependents and some savings to keep me going, I wasn’t under this constraint, even if it felt like the sensible thing to do. So for me, the best advice came from speaking to ex-patent lawyers who left early in their careers- they were the only ones who could empathise what I was going through.

The second thing is to be wary of how much advice you seek. Scrolling internet forums and reading books felt like important work. I needed to gather more data points. If I just keep reading, I’ll eventually find some clear direction, I reassured myself. But as Nassim Taleb mentions, data, especially in large quantities can be toxic. More opinions brings more baggage which is exactly what you don’t need. You need clarity.

Advice is a lot like sugar- it’s great in small doses. Otherwise, it’s addictive and has no nutritional value.

The right advice can help, like it did with me. But at the end of the day, the decision was truly up to me. Only I could make the leap. Without getting too cringey, it was that I had to have the courage and believe in myself.

So ask for advice from the right people. Not too much. And trust in yourself.

Just do it

The day finally came when I decided to pull the trigger. I’d given myself plenty of time up until this point. I was following my curiosity. I sought advice from those I could trust.

Yet even after all of this, I still felt scared. I was swapping the known for the unknown. The warmth of responsibility for the cold of freedom. I even wrote a poem about it.

I realised that no matter how much planning you’ve done, taking the leap is never easy. It still requires courage. You’ll never feel certain.

But there are questions you should ask yourself to confirm your decision.

The first is: Say you were transported to your 80th birthday. Looking back, would you regret your decision?

This is the same regret minimisation framework Jeff Bezos used when he made the leap to start Amazon from his high-finance job.

The second is to ask yourself: If everything fails, can I return?

For me, the legal sector was not going anywhere. Returning (if I ever wanted to) was always an option- I would simply need to interview again.

Answering these questions highlighted that the risk of change was not nearly as big as I’d thought. In fact, staying was even more risky given the possibility of me being eternally regretful of what could possibly have been, had I been brave enough.

With this, I handed in my resignation letter.

Never burn bridges

Now with your exit confirmed, it’s time to torch the place right?

Not quite.

I certainly did dream of heading straight for the exit.

But the world can be a small place. You never know when you’ll need people. Even if you never run into your co-workers again, you may need them for references, referrals, or heaven forbid, your old job back if you ever decide to backtrack.

Settle any outstanding work. Leave with dignity. Appreciate their efforts.

Your exit is hard for both sides.

Don’t look back but It will probably take longer than you think

As I left the office for the last time, it was time to ignore the whispers pulling me back to the past.

The focus was on the future. I remember feeling free, like a weight had been lifted.

I was eager to get started on my new path.

What I found was that it’s important to pace yourself.

Career pivots are rarely instantaneous. Like me, you may need to learn new skills, prepare for interviews, and eventually learns the ins and outs of a completely new industry.

It can suck to feel like a beginner again.

It can take to time settle.

So don’t rush. Give yourself time to adjust to your new surroundings. And don’t forget to enjoy the ride!