Doing it the hard way - My career journey failing forward into success

Published May 28, 2020, 8 min read, tagged as: motivationpersonal

No coding tutorial or bootcamp can prepare you for the feeling of having to tell your family that you don't know where your next paycheck is coming from because you didn't pass the job interview.

I've always loved computers so when I was 10 I gifted a book that changed my life. It was a book teaching Visual Basic 6. I didn't understand anything it said at the time so I was was introduced to a different, simpler language called Basic. I coded my first "Hello World" in Basic at the age of 11. I was instantly hooked! What followed was me spending my birthday money every year on programming books. Since then, I've been a developer working with JavaScript, PHP, C# and Ruby. I got my first paid contract at 16 and worked multiple jobs both in and out of tech since then, but for this story I'm going to focus on my experience since finishing university, because that's when I stopped working to live and started having to work to survive.

No coding tutorial or bootcamp can prepare you for the feeling of having to tell your family that you don't know where your next paycheck is coming from because you didn't pass the job interview. Nothing can prepare you for the feeling of defeat as you realize you're going to have to shut down your business. But I've had to face this reality so many times in my life.

I could feel sorry for myself about a lot things that have been unfair in my life. From being born to a working class family and not being able to afford the same experiences as others to having to close multiple businesses. I could have felt like a failure over and over again. But instead I forced myself to compartmentalize the negativity and instead focus on what I needed to do to be better.

Starting my first business

I packed everything I owned into a single suitcase, collected all the money I had which turned out to be less than $1000 and made a leap of faith.

My professional journey started in England where I spent the first 23 years of my life. I've always aspired to have my own business and when I finished university that was the plan. The problem was that my family had moved to the US, and those that have lived in England know how hard life can be if you're struggling financially.

I decided to make the move to be closer to my family and start my business in the US because I felt I'd be able to take bigger risks if I had a safety net to fall back to. I packed everything I owned into a single suitcase, collected all the money I had which turned out to be less than $1000 and made a leap of faith.

Within 2 weeks of making the move, I was introduced to the owner of 7 pharmacies in the Central Florida area that was looking to take his business online. The only problem was that just a couple of months before he had already had the same conversation with someone else and had a prototype in the works. I told him not to worry and asked if he would be willing to meet me anyway just to chat and see if he could give me any advice. Within an hour he was yelling at me for not coming sooner because he felt like I understood his vision better and ended up cutting his losses and asking me to redo everything that he'd had done up to that point. Things were looking good!

Over the next few months I had steady work coming in and met some great people to partner with along the way. One ended up offering me a substantial amount of money to partner with him 50/50 with the promise that he'll teach me everything he knows and together we'll grow the business much bigger than I would be able to do by myself. I'd be crazy to turn an offer like that down right?!

Well, as I found out 18 months later, things don't always work out how you imagine. We didn't have a conversation up front about what we expected of each other and both ended up at a loss. My expectation was that I would be able to rely on my partner to manage the business side and grow it while I focused on the technical side, while he expected me to carry on doing everything and just ask for help when I needed it. The lack of growth created a debt that the business was unable to repay and I ended up having to make the painful decision to shut down and part ways.

Shutting up shop and starting over

Unless I spent another 6 months developing there was no way I was going to be able to sell this thing.

In the meantime I'd been thinking a lot about the e-commerce space and how at the time there weren't many options for small businesses. I'd already met a lot of small business owners when I was freelancing, so I knew I'd be able to make something useful for them. I went and talked to a bunch of them and found out what type of features they'd look for and then set out to try and create a product that would work for all of them. 6 months of 18 hour development days later I had a product that I was certain every small business owner would be throwing their money at. How unbelievably wrong I was! By trying to create something that tried to work for everyone, I'd created something that didn't work for anyone. Everyone i talked to said the same thing - "It's almost there, but you'd have to make some tweaks for it to work for us." That lack of product-market fit really hurt. Unless I spent another 6 months developing there was no way I was going to be able to sell this thing. But I had another problem.

Me and my then fiancee were trying to get married. But I had no money left. There was no way I was going to be able to support someone else if I couldn't even support myself. So I made the hard decision to once again close my business and started working on my resume.

Moving into employment

I wanted to use my talents to make the world a better place and I just didn't feel I was doing that.

My luck turned. I found a promising position and applied on a Wednesday. On Thursday the company called asking to set up an interview for the next day. On Friday I had my interview. During the interview I took my laptop and showed them the code for my e-commerce solution. They seemed impressed! We parted ways with them asking if it's ok for them to call me over the weekend if they decide to go forward with an offer. Saturday afternoon I got the call and was asked to start on Monday. Things we're looking up! Except... not really.

I hadn't realized it at the time but I didn't really know too many specifics about the product the company was creating. They kept on describing it as email marketing software but didn't go into too much detail about what it actually did. I found out over the coming weeks why that was. The company was using the software to sell "magic products" to vulnerable and unsuspecting people. Everything was technically legal, but morally in a gray area. They would use clever tricks to make it seem like they are talking to a psychic who knows everything about them. In doing that they had created actually a really smart email marketing system with dynamic campaigns and intelligent segmentation.

For a few months I convinced myself that it's fine because I was working on the product itself and not the business that actually uses the product so I'm not directly involved, but my conscience got the better of me and I ended up deciding to leave because ethically I couldn't do it anymore. I wanted to use my talents to make the world a better place and I just didn't feel I was doing that.

Getting into the grind

They were blown away with my practical demonstration and proactivity. I knew I had the job! Things were finally back on track. I bought my dream car! I bought my first house! Life was great...

What followed was a few years of taking short term contract jobs. I didn't have stability but the money was great. Eventually I got an interview that I was really excited about. It was a remote position for a really interesting agency that was hiring an AngularJS developer. I wasn't too comfortable with AngularJS yet but I knew I wanted to learn and I knew I'd have to do something special to stand out during the interview. I went on the companies website and saw a really cool grid on their company page that had all the employee pictures. I decided to recreate it in Angular and showed it during my interview. They were blown away with my practical demonstration and proactivity. I knew I had the job! Things were finally back on track. I bought my dream car! I bought my first house! Life was great... until it wasn't.

Making big life changes

I got promoted all the way to Director of Engineering and now run a team of 15 engineers, am responsible for all the major technical decisions across the companies product suite and own a budget of just under $1m a year.

In summer of 2016 my wife asked for a divorce. What's worse is at the time I didn't really understand why. As a developer I'm used to feeling imposter syndrome with my work, but I'd never felt imposter syndrome in my life. I didn't know what I'd done wrong and so decided that everything I did was wrong. This mentality effected everything. My personal life, my relationships and even my work. I didn't know who I was anymore. I spent a year in depression, constantly forcing myself to do things that took me out of my comfort zone because I was so desperate to be someone else. In hindsight I did a lot of the right things but for the wrong reasons. I started going to the gym, I wrote a book, I went to public speaking classes and I started a YouTube channel.

March 2018 was a month that totally changed the course of my life. First I reconnected with an old friend who I hadn't seen in years. She noticed I wasn't same person I used to be and told me she wants to help me get better. Another was an old colleague who had started a business with a couple of people in the healthcare technology space. At the time I was interviewing at Facebook and Universal Studios and both were looking promising but my friend gave me some great advice. She told me to take a risk with the startup, the other two will always be around if it doesn't work out.

That turned out to be some of the best career advice I've ever had. I started as employee number 6, and their first developer. In the time since then, the company has grown like crazy and so have I. I got promoted all the way to Director of Engineering and now run a team of 15 engineers, am responsible for all the major technical decisions across the companies product suite and own a budget of just under $1m a year.

Where I am now

No coding tutorial or bootcamp can prepare you for the feeling of telling your family that you got the job. Nothing can prepare you for the feeling of victory as you realize you've achieved your goal and are living your dream.

That brings me to today. I'm sitting here next the friend who found me at my lowest and helped me find the self confidence I needed back to being my best again, and I'm so happy that I can now call her my wife. I have a great family and I work for a company that lets me use my talents to make the world a better place. On top of that, I work a job that gives me the influence to help others reach their goals and dreams. I'm even writing a book about my experiences and everything I've learned on my journey. Best of all, I'm less 2 weeks away from meeting my newborn son. At the time every failure felt like a setback, but now I can see they made me the person I am today.

No coding tutorial or bootcamp can prepare you for the feeling of telling your family that you got the job. Nothing can prepare you for the feeling of victory as you realize you've achieved your goal and are living your dream. I'm thankful that i've been able to face this reality.

I tweet about this type of thing a lot. If you enjoyed this article, you may enjoy following me.

April 08, 2020, 1 min read
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