How to leave your cushy desk job || Engineering and Leadership

[Note from Pat: This is a post from my friend and engineering classmate Tyler Watkins. Tyler has just made a major move in his life to leave the traditional workforce. This is a letter he wrote to anyone who has ever thought about doing the same, but could never bring themselves to take the leap. You can see more of Tyler’s excellent work on fitness and living better at]

A few weeks ago, I decided to leave my well paying job in the corporate world. I’m 30 years old. I have worked 5 years as an Engineer, and 2 years as a Technical Sales Engineer. Many of the colleagues I left behind told me they would love to do the same. This letter is written to them to help them reflect on their career and way forward.

Dear Friend,

You work hard. No one can deny that. It’s in your nature. It’s very likely a skill that your parents instilled into you as a child. To achieve, to accomplish, to not let them down. You’ve carried that skill over to your working life and whenever your boss asks you for something, however unrealistic or last-minute you do whatever it takes to meet that deadline. It’s in your nature. You’re a pleaser. You’re a high achiever. You like praise, I understand that. But what’s more important is that you hate to feel inadequate. You hate to disappoint. It gnaws at you. If not through the eyes of your boss you still see yourself through the eyes of your parents. Living up to their expectations.

That’s the first challenge we face when thinking about leaving our corporate jobs. To say I’ve done enough and walk away from the expectations your parents had for you. You’re a grown up now. You know that. I know that you know that. However, I still know that you and I want to make our parents proud. Maybe we will feel this way until they die or we die. This is a difficult thing for you and maybe it was easier for me. Because I out achieved my parents quite quickly. I made more money in my 20s than they made in their entire lives. I had more traditional success than they ever could have dreamed of. Maybe that’s why I was able to overcome this challenge and say “I’ve done enough”. But what does it mean to have done “enough” for you? Is it a dollar value in the bank, or a certain position in the company? Or does it more realistically, fundamentally, come from your decision to finally value your own perspective and life? It’s realizing that your parents grew up in a different world than we did. And that their expectations are based on the perspective of their time. That they have expectations of certain external accomplishments for you but that maybe those accomplishments no longer align with what constitutes a good life. Your parents did the best they could for you based on what they knew. However, it’s your job to decide what is important to you and choosing to do something different and walking away from your job is not the same as walking away on them. You are choosing to do something different. You could have made it in the world they envisioned for you but you are choosing a different path, it’s your path based on your perspective and they should accept it. Or maybe they won’t.

The second challenge is about money, and the things we buy. Trips to Dubai, Turkey, Morocco. Land cruisers. 5 star hotels. 4 bedroom apartments where only 2 people live. I know you’ve gotten used to these things. And they are nice. It’s nice to eat dinner at a fancy restaurant and not think about the bill. It’s nice to take a trip and go driving in world class sand dunes. But wouldn’t you enjoy that trip more if you weren’t answering calls from work from the passenger seat of your land cruiser as your wife drives through the sand dunes? Or working on your laptop on the airplane because there just wasn’t enough time to finish everything before you left. You know that you can never finish everything, right? I appreciate that you are very good. They wouldn’t call you if you weren’t. I appreciate that there is nobody else and the company needs you. It feels good to be needed. But it also sucks the life out of you. Yes, we have nice things and take fancy trips. But I’m going to ask honestly: do you enjoy them? When was the last time you saw a sun set from your apartment balcony overlooking the sea to the west? Actually, when was the last time you were out of the office before sunset? If we decide to chase the nice things we will always come up a little short. They make million dollar cars so guys with hundred thousand dollar cars will feel inadequate. There’s no other reason they exist. With a million dollars you can retire anywhere in the world. I’ve done it with much less. Moving up the ladder, making more money to buy more things that really add nothing more than a sugar high to your life temporarily is fucking stupid. It makes no sense.

What really makes you happy? Think about it. Is it time with your family? Friends? Did you used to play music? Hockey? How much did these things cost? The cost for me to do Brazilian jiujitsu is $60 a month. I used to make $60 per 40 minutes. Scale that out. When I started doing the math I realized I was making enough in 1 month to live my dream life for 10 months if I didn’t get caught up in buying all kinds of stupid shit. You don’t need a lot to be happy and live a full life. You know that. So then the question is how much do I need? When will I have enough to walk away? There’s no magic number. For everyone it’s different. But I will tell you this, the more I earned the more I thought I needed. The end was just around the corner but never quite there. I worked an additional 8 months after having “decided” to leave because I just wanted to top up a little more money. But I’ll tell you what helped me in the end. I came to my number first by calculating the cost of my monthly expenses if I spent the minimum realistic amount on basic necessities (transport, housing, food, etc.) and added the cost of my favourite hobbies and things to do. I could live for 13 years on my savings. And if I invested my money in inflation-proof, cash-returning assets like rental apartments, I could essentially live indefinitely. This was shocking and overwhelming to me and if you do this exercise you’ll soon realize that this feeling of insecurity about what you don’t have is ridiculous and only matters if you get caught up in the more, bigger, better game of keeping up with the Jones. You very likely already have enough.

So what else is keeping you here? Security? Health coverage? Alright, that’s reasonable. But let me ask you about your health for a minute. Didn’t you have to see a specialist last year about your lower back pain. What did he have to say about it? Your back constantly hurts, your eyes get worse year over year, you’re hearing impaired and you are going bald and grey at 35. Yes, the company pays 80% of your health coverage but how much of that treatment is needed because of the lifestyle the company imposes on you. Do you really think you’d have all these issues if you weren’t working 7am to 9pm at a desk. Hunched over, writing excel spreadsheets, making calls, meeting deadlines, missing sleep and having zero time away from work to refresh, relax and live?

What else? Do you really care about moving up in the company? Do you care about your career? If you say yes, fine. But really ask yourself why? Is it about status? What the hell is status anyway? Your driver picks you up in the morning and calls you sir, your office has a window, your name is plated on the wall next to your door. Status in the context of a company is kind of strange. Status in the real world is based on respect and value among peers. Status in a company is really based on how many people I can get fired. What about your job title? Honestly, no one really knows what we do outside of our company. And even inside the company no one outside of your direct reports and venders trying to sell your company something care what your job title is. Even if you make it to the top and become a VP. No one cares except other people in the company who are trying to get to the same position or not get fired. If what is really important is respect from those who matter, that comes from your character, not your position. And your character is already very strong. You’re a good person who gives value to other people’s lives. You are enough without needing some position to feel that way.

So what else? You’re too old to be trying to please your parents, the money doesn’t matter, status is a joke. What else is keeping you here? Maybe you have a good answer this question. In the end you’ll have to face these questions yourself right. And come to whatever conclusion you do. I faced them. It’s not easy and I won’t even say that I’ll never work in a corporation again. Maybe I will. Who knows. Life changes and there are times in life that can justify the decision. But at least for now it made sense to leave and do something else. And enjoy the rest of the world. Because we are aging quickly.

And because I’ve done enough, I have enough, and I am enough.



Like what you read? Get free updates!

Join our mailing list to receive the latest from the E&L Website. You'll also get enrolled in our 12-week e-mail based engineering leadership course for free!

Great! Just check your email for the next steps...

Pin It on Pinterest

Share This