Lesson #1: It's okay to be on the Titanic if it's your first boat ride
So, first things first, let's take the pressure off.
At the beginning of your career, you can make some shitty bets that don't work out. This is fine. Try to avoid it if you can, but it's not the end of the world if you join a company and they tank a few months later. It is not a reflection on you, and interviewers will see that. What matters most right now is getting on the ladder and getting a body of work started.
Early in my career, I changed jobs often. I thought this was a poor investment decision, but the market has caught up with me; most developers now switch jobs every 2 to 3 years. I'm ahead of the curve at around 18-24 months, but not much. What matters is that I can demonstrate value in both the idea and execution stages.
Lesson #2: Reputation 101 – how to beg borrow and steal
When you join a company, you borrow a part of their reputation and incorporate it into your own. You will see people on LinkedIn and Twitter writing 'ex-Google', 'ex-Facebook' in their bios. Working at an organisation like this is a badge of honour, legitimising you as you move through your career.
Some people care about this, some don't – but I would be lying as a hiring manager if I said I didn't notice it or it didn't influence my decision. If you're good enough to work there, you're good enough to work here, thinks the hiring manager.
However, I've never worked at one of those companies, so perhaps I'm fickle and jealous. Who knows? YMMV.
Lesson #3: Stay sharp, stay ready, stay relevant
A few years ago, I was the CTO of a reasonably small organisation in Stockholm. It landed in my lap, but I loved it, primarily because the team around me was (and still is) a brilliant group of individuals. I am blessed to have worked alongside them.
Still, this was over four years ago – so the experience is stale now. Has being a CTO changed that much in the last four years? No. But it's not the most recent thing on the top of my CV, so it's a hard sell.
So, I jumped down a career level into Head of Frontend. Same experience, same lessons, same way of working – different title. Adapt to stay relevant as you move through your career.
Lesson #4: You go where you look – so don't look down
Companies, like all things, are never static. Either they are growing, or they are in decline. Growing is easy to spot – you're hiring like crazy, companies are throwing trunkfuls of cash at you, there's a buzz about the company – it seems like everyone wants to work there.
Declines, however, are much more subtle. People think that companies die with a big bang and a crash. However, this is rarely true. Often death manifests as a slow nosedive into capitulation and irrelevance. Leadership struggles to set direction, lose key staff in crucial business functions, and don't seem to break ground. Progress comes to a halt. You see these signs, head for the exit immediately.
If companies do not adapt to the ever-changing environment, the market, they will die. Use this as a yardstick to figure out when is the time to perform the next manoeuvre in your career.