Reading Time: 8 minutes

I’m always hesitant to give career advice. While I’m proud of my career so far, I’ve had a few lucky breaks and help from some very smart people. This makes it hard to feel qualified to guide others myself.

However I’ve recently been reflecting on my journey and where I’ve made some good decisions. I’ve also made lots of mistakes, and where there are mistakes there are lessons. There aren’t many posts that cover this topic for product people, so I thought I’d write a few of them down. The following is by no means product-specific, but my experiences were formed in that context.

After that quick intro and caveat – here are a few things I’ve learned, that I would urge every product person to think about:

Understand that good things won’t just happen to you: It isn’t easy to have a successful career. As much as your employer might want to help with your career development, the truth is that at most they will only help in a micro way, helping you to learn and gain new experiences. For example; it’s unlikely that they will ever advise you to leave the company when a new opportunity comes along, because they’re not incentivised to do so.

And in the ways that they might genuinely want to help, it will still always be priority #3 to them (behind their own career, and what’s best for the company).

So think hard about what role you want to be doing in 5 years time. Talk to people in roles you might want to have one day, both inside and outside of your company. Take ownership of your plan, and your decisions. It’s hard, but it’s worth it.

Know what you’re optimising for: People aren’t successful by accident. If you want to have a great career, first you have to work out what that means for you, and only then can you plan for it.

In your life, you make relatively few big career decisions (e.g. moving companies, or changing roles). The scarcity of these decisions makes each one incredibly important, and the easiest way to make a good decision is to define what good means to you.

When I think about my career, I plan for three major factors: learning, income and fun. Learning is good for future income (more on this next) and typically the thing I value the most. Income is salary, share options, bonuses etc, and is where my needs change the most depending on personal circumstances. Fun is simply how much I enjoy work, and is normally a veto factor (e.g. extremely boring, or immoral environment), rather than a reason to choose between two good opportunities.

Over time, the relative importance of each factor changes. For example, when my son was born my threshold for fun increased (I needed to be able to have a clear head in the evenings). When I worked a job where I hadn’t learned much in a while, my desire to learn more heavily influenced my next move.

Every time you choose to stay at a company (and not even look for another opportunity), you’re making a big career decision. I encourage you to reassess your job every few months, to make sure it’s still reflective of what you want to achieve.

Optimising for learning is optimising for earning: All the best advice rhymes. Generally speaking, your remuneration (salary, bonuses, share options) will increase exponentially as you become more valuable to your employers, and that value is almost entirely a function of what you learn.

Your skills (executional, strategic, leadership, organisational, and technical) are what companies pay for. So if you want to maximise your earnings in 10 years, find somewhere that you can learn the most now.

So how do you optimise for learning? There are two aspects I’ve found, that help here.

Learn out-of-hours: I genuinely hesitate to give this advice. I’m lucky enough to genuinely enjoy building digital things, but I know not everyone does. I also know it can be much harder for certain people: parents, carers, people with multiple jobs etc. With that acknowledged, I do think it’s a useful way to increase your rate of learning.

I read books obsessively (audiobooks still count, right?). As I’ve written about elsewhere, the fact that people have written down their own experience and are willing to share that with you for a tiny fee is an amazing blessing. I wish I’d started reading earlier in my career. Once you get going, there’s no shortage of amazing relevant books.

I also find side-projects are a fantastic way to learn. Side-projects helped me learn about the process of building a website, building an app, getting press from a launch, getting feedback from customers, and how to use different technologies. I don’t believe that there is any such thing as “people that can’t code”, only “people that don’t code yet”. The reason that side-projects are so useful is that you don’t have to optimise for revenue, or anything like that. You can selfishly optimise for learning about the thing that you want to learn, so that you can maximise the value you get from it. At your day job, you’ll never be able to be selfish like that.

With both reading and side-projects, you won’t immediately become better at your day job. But it will help you to have more context on what you’re doing, and I promise you that the things you learn will come in handy and help you progress.

Choose jobs to optimise for learning: In terms of choosing jobs, I look for two things: smart people, and hard challenges. I consider smart people as those with experience of doing hard things, normally this means they’ve been at good companies early on (when things were often hardest).

Smart people will teach you what they know. What took them 5 years and a lot of work to learn, they can teach you in a fraction of that time. You will learn from watching them work and from working with them. A side-benefit of working with smart people is that they’ll form part of your network, and they’re useful people to have in there.

On hard challenges, you’ll learn most in an environment that forces you to think hard. Hard challenges are like training for any kind of sport – they harder you push yourself, the more you become used to it. Regular challenges suddenly feel very easy. As an example, my Dad is a surgeon and attributes his own learning rate to starting as a junior doctor in a Johannesburg A&E. The first patient came in holding his left hand in his right hand, and the second patient came in with a machete in his head. After working in that challenging environment, regular surgery became somewhat easier to handle.

Another benefit of challenging environments is that they also make smart people work harder too, which means you’ll learn more from them.

Join a fast-growing company: The best way to find smart people and hard challenges is to find a fast-growing company. Lots of environments can be challenging, but fast-growing companies will be constantly challenging in new ways and you’ll need to learn new skills very quickly as the need arises. These companies will also most likely be founded by smart people, and attract smart people.

It’s a great environment in which to learn quickly, and having fast-growing companies on your CV sends a good signal to future employers.

The fast-growing company will generally mean that you do things frequently. There are always more things to do than people to do them, so you’ll be constantly making decisions, executing, and working with people. This frequency at which you do tasks is (in my experience) almost entirely correlated with the rate at which you learn.

In his book “59 Seconds”, Richard Wiseman tells of the benefits of a frequent work, citing a study of a photography class. Half the students were told they’d be graded on the quality of every piece of work, the other half on the quantity that they produced. In the final projects, those in the latter half performed significantly better, due to their extra practice. Find a job that will let you do the things that you want to learn.

Know when you’ve outgrown your role: The biggest blocker to being open to roles that might suit you better is often some strange sense of loyalty. I say ‘strange’ because companies are rarely loyal to employees – they won’t fire you at the first opportunity, but when relationships that no longer serve their best interests, they won’t keep you. So you shouldn’t worry about it either, if the relationship is no longer optimally beneficial to you.

Every few months, assess if your role still best suits what you’re trying to achieve. If you’re looking to progress up a level and the opportunities simply aren’t available, speak candidly with your manager to understand when they might come. They won’t look down on you for asking – in my experience the opposite is more likely to be true. If opportunities aren’t going to come that you want, go look for them.

Understand your company strategy: Are they raising funds? Are they prepping to sell? Are they building maintainable growth? Are they aiming to control a decline? Understanding this will put everything else into context, and accelerate your learning.

If this information is available, be interested in it. If it’s not, ask for it. If you can’t get it, consider moving to somewhere where you can. Don’t worry about asking for this information, it shows that you’re interested and cares, and any good manager will be pleased that you asked.

Broadly speaking, you can think about features and improvements as executional actions, based on strategy, which tries to achieve a vision.

An example company, showing the link between vision, strategy and execution.

The more you understand the vision and the strategy, the better you can decide if the executions fit in with what you’re trying to achieve. This strategy and vision is also the work that senior management owns – understand it and help with it, and you’ll be more equipped for that level of conversations.

Negotiations: Your objective in negotiations is to get the best possible deal for yourself. You should get your head around this, and not feel guilty about it. Companies are trying to pay the lowest for you that they can, and they don’t worry about it. If you struggle, think of your salary is someone purchasing your time. As with any auction of a valuable item, the market price is the highest price someone is willing to pay.

Moving jobs is the best opportunity to get a salary increase as you’re not bound by internal salary caps, so make the most of these opportunities.

If a potential employer asks, don’t tell them your current salary. It’s entirely irrelevant, and you’re under no obligations to tell the truth anyway. If you have just taken 2 months holiday and are looking for a job, your current salary is zero. Or if you’ve been working for a charity, and are now going to work for a bank, your expectations change. These examples should show how irrelevant it is.

When companies ask your expected salary, it has nothing to do with you getting the job, it’s the first move in negotiations. When they ask for your expected salary, make it high. There’s a risk that they’ll say they can’t afford you, but you can always say that you’re willing to hear a lower offer. Just because you set your target salary high doesn’t make them want you any less. Psychological studies say it’ll make them want you more.

Take opportunities, don’t wait for them: If you want more responsibility, seek it out and find it. I often hear managers say “when people are ready for a job, they’ll already be doing it”.

Granted, it can be hard to know what these opportunities are, or what you can do without treading on others’ toes. Simply asking your manager can go a long way to help this.

If you’re performing your core job well, and have some spare capacity, make your manager aware. As with so many of the points above, they’ll only be impressed, and pleased that you’ve offered to help with other things. This is you taking an opportunity, by asking for it.

No one can ever tell you what decisions to make, because the things you’re optimising for are so personal to you. So whatever you’re optimising your career for, make sure to make deliberate decisions to get it, and to choose whatever is best for you.