Choosing the Right Path

Srijan Singh pinged me on LinkedIn earlier today with a question:

I’m in my early career as a backend dev at IBM, and something I often wonder about is choosing the right path: whether to stick with a big company and learn deeply, or test myself in a startup environment (remote vs in-person adds to the mix too). Since you’ve navigated such diverse experiences, I’d love to hear how you’d approach that decision early on.

I quite enjoy getting these kinds of questions, but as Scott Hanselman wrote way back in 2010:

 If you email someone one on one, you’re reaching that one person. If you blog about it, you get the message out on the web itself and your keystrokes travel farther and reach more people. Assuming you want your message to reach as many people as possible, blog it. You only have so many hours in the day.

So here’s my answer to Srijan’s question, as a blog post.

Let’s start with the simple answer, which is how I did approach that decision early on… I didn’t, really. I was lucky enough that I didn’t really have to think about it. I loved working with computers, writing code, and building websites, and if I was getting paid money to do that I was happy. I landed my first graduate role in 2000, via one of my housemates who was working as a recruiter; three years later one of our clients, Spotlight, asked me to work for them full-time; fifteen years after that, I got head-hunted by Skills Matter to become their CTO; they went bankrupt in 2019, I set up my own company, Ursatile, and I’ve been independent ever since. To put this another way: I’ve had exactly two job interviews in my life, and one of those was to stack shelves in a grocery store when I was sixteen years old.

That probably doesn’t help, right? 😆

Looking back over 25 years of working in software, though, I think there are three things that matter:

• The problem. Are you helping people? Are you making somebody’s day better? Are you building something that’ll make your end users happier? Or is your entire working life about making the CEO’s stock go up another point?
• The people. Who are you working with? Are they competent? Are you learning from them? Do you enjoy their company? Do they respect your ideas?
• The process. How does stuff actually get done? Everything from prioritisation and planning to what text editor you use. I enjoy working with some technology because it makes it easy for me do good work. I do not enjoy working with some other technology, because it makes it hard for me to do good work.

You don’t need all three. I’ve had bits of my career when I’ve been working with awesome groups of smart, kind people, using great tech to solve cool problems. I’ve also had bits of my career when I’ve been using painful tech to solve pointless problems, but the people made it worthwhile - and, occasionally, periods where I honestly didn’t care for the people or the problem, but was learning so much along the way that I probably stuck around longer than I should.

Think about longevity. You’re building solutions, relationships, and skills. Will the things you’re building last for a decade, or will they be obsolete by the end of the year? Can you take those things with you out into the wider world, or do they only have value in the context of your current role?

Remember to take stock once in a while. You might find the job that used to tick all three boxes is down to two, and then one… and when you’re down to one, you’re in danger, ‘cos if that one disappears too… well, congratulations. You’re stuck using tech you don’t enjoy to solve problems you don’t care about with people you don’t like.

Now, obviously there’s a huge amount of context to consider here. The tech jobs market is the worst I’ve ever seen; more of my dev friends are out of work right now than at any point since the first dotcom bubble, 25 years ago. If you’re supporting a family or paying off debts and you have a steady paycheque, maybe just keep your head down, keep doing what you do, wait for things to pick up. But if you’re early in your career, you’ve got a bit of financial security and you’re unhappy with how you’re spending your working days? Do something different. Bored of working in the enterprise? Find a startup. If you’re burning out working in a startup, get a comfortable, predictable job in a big company. If you’re remote, and tired of being at home all the time, find a job with a nice office; if the commute is making you miserable, try remote. When you try something, give it at least a year - but if you’ve lasted a summer and a winter, learned the ropes, learned the industry, and you’re still miserable? Probably time to move on.

Really, though, the important question when it comes to career progression isn’t “where do I see myself in five years”, it’s “am I going to quit my job today?” That’s the question that actually makes things happen. If the answer’s “hell, no, I’m happy”? Awesome. Go to work. If the answer’s “yes, today’s the day!” - well, good luck with it.

But if the answer’s “I don’t know”? Well, time to gather some more data.