My Great Escape From the Corporate World | by Ryan James | May, 2022

Why joining a startup was the best decision I’ve ever made as a software developer and how I did it

Photo by Lala Azizli on Unsplash

Are you feeling stuck in your current job? So did I for a long, long time.

I had been feeling incredibly pent up in every way. Physically, emotionally, creatively, and mentally. I saw the next 45 years of my life flashing before my eyes.

I was working a typical 9–5 job developing software at one of the world’s largest banks. I was commuting two hours each day to work a job that brought me absolutely nothing — paying no emotional dividends.

The pay was good, the benefits were exceptional, and my coworkers were fun. I easily could have packed it in for the next 40 years and retired at 65. But one key piece was missing: fulfillment. So why was I working a job that didn’t challenge me creatively? Why was I working on software that didn’t make a difference in anybody’s life?

Perhaps the long car rides (and one too many self-help audiobooks) forced me to become even more self-aware than I already was. What was the point of my work? If I die today, what will be my legacy?

Here lies Ryan, a nice guy who wrote stable and efficient code to help customers get mortgages faster.

And this is fine. This reflection isn’t a knock on anyone who works on mortgage software. It’s just not for me. It’s not the difference I’m looking to make in this world. I’m a builder, a creator. I want to build something end to end and see how it directly impacts its users.

I want a part of myself to be in my work, and I want to feel the joy and excitement of the people using what I’ve built.

It was time I needed a change.

Understand the steps I took to escape my corporate job.

Note: This article reads in a story-like fashion; However, the lessons from each section are independent. So, feel free to skip around.

My mind felt like it was in an artistic prison. Everything at my corporate job had to be done in a certain way. Anytime I wanted to introduce even the littlest bit of creativity into the application, it needed to pass through eight levels of approvals and ultimately get rejected. Eventually, I would say, “You know what? Never mind, it was a dumb idea.”

After so much oppression, I turned my creative energy elsewhere. That’s how I landed here on Medium.

A place to give back to the developer community, a place to share and receive feedback on ideas, and a place to let my mind be free.

After a few lessons learned, I felt there was so much about this space that wasn’t entirely obvious. I wrote an article if you’re curious about some of my lessons:

As the great Creed Bratton from The Office once said,

“The only difference between me and a homeless man is this job.”

As my job wasn’t getting the best out of me, I felt entirely too disposable.

Imagine you host a potluck (an event where everyone brings a food dish to contribute to the dinner) every week. However, one of the guests consistently shows up empty-handed. Everyone else is pulling their weight and bringing different items, but they always show up with nothing and eats everyone else’s food.

Eventually, you’re going to stop inviting this person.

This is how I felt at my job. I felt like I could have been let go at any given time. When my best abilities and talents aren’t being brought out, I’m the same as everybody else. The other people could quickly reproduce the little that I was bringing to the table. So I was a waste of a seat.

And when you’re disinvited, you have no income. This was when I started writing on Medium.

After just six months of writing on Medium, I could survive on the passive income it generated for me. This newfound financial freedom allowed me to take risks I wouldn’t usually take.

As I searched for content to write about on Medium, it forced me to think about specific ideas and concepts differently. It became less about “how do I do this” and more about “how can I train a six-year-old to do this.”

This way of thinking forced me to thoroughly understand the concepts I was writing about. If I didn’t fully understand it, I would be exposed by my readers. trust me; This Medium community will let you know when you are wrong.

You are fully accountable for anything you write in your articles. So don’t bullshit your readers.

But the point here is that I found I was becoming better and better at my job because of the different perspectives and deep technical knowledge I had of new information.

And not only that, it’s a way of documenting your thinking. It’s a snapshot of a time when you thought profoundly about a particular topic.

For example, if I’m training a junior software engineer and they’ve never implemented a REST API, I have an article I can point to that’ll walk them through the process step by step. Then I can answer any remaining questions they have after reading the article.

Writing down your thoughts solidifies your understanding of a topic and will save you time and energy when asked about said topics.

Employers love developers who document. Showing an employer that you enjoy writing and linking them to your work will help you.

It shows you are taking the initiative in working on these side projects, but you’re also taking the time to document them and explain them to the world.

Also, it forced me to challenge myself in different ways. I searched for other ways to develop new content and came across the AWS certifications. I took two of these certification tests and documented them every step of the way.

Not only did I come out with two highly in-demand certifications and a ton of AWS knowledge, but some of my most popular and profitable articles (I was able to pay for the certifications not from my earnings).

Would I ever have done this if I didn’t start writing? I honestly do not think so. Here’s a link to one of those articles if you are curious:

It’s incredible how much more confidence I had going into job interviews after this journey.

Not only did I have a more extensive portfolio to show off, but I had an incredibly in-depth understanding of everything I said I knew.

Employers can sniff out inauthenticity in a heartbeat, and I no longer had to worry about that.

Not only that, but for the last six months of working at my corporate job, I no longer felt like I was wasting my life away (only 40 hours a week now). The creative outlet I got from Medium gave me something to look forward to when waking up in the morning and going home from work each day.

I was working two jobs and did not mind.

When searching for a new job, I limited my options to startups. This was the best decision I’ve ever made. I went from a company with ~200,000 employees to a company with 90.

I wrote this article about two years ago when I first joined the startup. Flash forward two years, and the company is now double its size. I was promoted three times and currently hold the title of director of engineering (software engineer I → software engineer II → lead software engineer → director of engineering).

The lesson here is that sometimes you need to get out of your current situation because you genuinely do not know what the rest of this world has to offer.

My voice is much louder, my creativity doesn’t get shot down immediately, my work ethic is on full display, and I’m finally writing software that helps people. I no longer feel like a cog in the machine and feel less disposable than I ever have.

Not only that, I get to work with the people I’m writing the software for. Nothing makes me happier than the look on their face when our product works the way they want it to.

There were times when I worked at my previous job, the big financial corporation, where I felt I didn’t have a choice. They offer short-term incentives (end-of-year bonuses, promotions, etc.) to keep you and make you think if you want to switch what you’re working on, you need to make an internal move. I am here to tell you there are other options!

If you are feeling pent up, explore what else is out there. It will do wonders for you. If you are not feeling confident about your skill set, invest in yourself.

It will surely pay the dividends you deserve.

If there is one word I would use to describe my transition from the corporate world to the startup world, it would simply be liberating.

If you’re feeling tied down by your job, there are ways out. You might have to work for it a little, but it’ll get you to where you’re meant to be.

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