A career ending mistake

From Code For Your Life

You came for the schadenfreude, but you’ll stay for the thought-provoking advice

This isn’t about the time I inadvertently shut down one of Britain’s nuclear power stations, an entirely true story for which the world is nevertheless not yet prepared. Nor is it about the poor junior developer who accidentally destroyed the production database on their first day (they’ll be fine, bless them).

Instead, I want to talk about another kind of career ending mistake, one that affects more than just the unlucky few. Indeed, it’s a mistake we’re probably all making right now. And that’s not planning the end of our careers.

The end

By “the end”, I don’t necessarily mean picking your retirement date. This is really about the aim or goal of your career. Where will you be when you realise that this is where you’ve always wanted to be?

If you love what you’re doing now and don’t ever want to change jobs, great: you’ve reached the end of your career, even if it plays out over many decades. If you don’t love it, though, and that’s much more likely, then it’s worth asking what job you would love, and how you’re going to get it.

So, where do you want to end up? And is that where you’re currently heading? If not, what should you do about it?

Out of control

The word “career” means, among other things, “to rush about wildly”, or, of a vehicle, “to move fast and in a way that is out of control”. Isn’t that apt? And doesn’t it describe the career experience of most of us pretty well?

The indispensable first step to getting what you want is this: decide what you want.
—Saying

Most of us, in fact, don’t really know what we want to do with our working lives until we’re more or less doing it. By the time we’ve made our minds up where we want to go, we may already be a long way down the wrong track.

It’s not surprising, then, that many of us find ourselves in less than fully satisfying jobs, with doubtful or non-existent prospects for advancement. In all honesty, if we are happy in our jobs, it’s probably more often a matter of luck than of design.

Maybe rather than rushing around wildly, we should give a little thought to what we want to achieve in our careers. Rather than just sit back and hope we get the career we want, maybe we should actively plan and take steps to bring it about.

As software engineers, we’re constantly making detailed, elaborate plans for computers to execute; that’s what software is, after all. Isn’t it kind of weird that we rarely give a moment’s thought to the program we want to write for ourselves?

Choose your destination

The best time to start a pension is always twenty years ago, and career planning is a bit like that, too. By the time you realise you need it, you usually wish you’d started a lot earlier. On the other hand, it would be foolish to let that prevent you from starting at all. Even a late, sketchy, and uncertain plan is way better than no plan.

So what would a career plan look like? And when should we start making it?

The first phase of your career is probably too early to make serious plans, and any decisions you make at this stage are rarely critical: there’s plenty of room to experiment and make mistakes.

In the final phase, by contrast, you have fewer options, and there’s not much time to pull off a significant change of direction. The autopilot tends to lock in and steer you further down the glide path you’re already on.

You should be planning, in other words, to enter the final phase of your career in the right position, at the right level, and at the right time to land where you want to. So where is that, exactly?

Three kinds of careers

Your career is likely to encompass lots of different things. Over the years, you’ll do all sorts of different jobs at different companies, and the perfect career destination for you may end up being something you can’t even imagine right now.

To help us think about it, though, let’s divide the possibilities, very broadly, into three groups:

1. Seniority
2. Management
3. Independence

In the rest of this article, we’ll take a closer look at each of these destination airports, check out the local weather conditions, and ask what kind of flight plan would get us there.

So, what kind of career do you want to have?

Seniority

The first kind of career destination we’ll consider is senior individual contributor (IC), which usually means something like “high-level engineer”. A senior IC doesn’t run their own firm, or work independently. They’re at the top of their game technically, and may be a technical leader for others, but they spend the majority of their time doing the work, not managing other people who do.

What does a senior IC do?

The exact ranks and job titles for senior engineers vary from one company to the next, and there may be many levels for you to achieve within a given company. But in terms of your eventual career goal, let’s say we’re talking about the top level you can reach while still being primarily an engineer.

In a small company, that might simply be something like “senior developer”, or even team leader. In larger companies, the pinnacle of engineering pay and responsibilities might be called something like “principal engineer” or even “distinguished engineer” (sounds good, doesn’t it?).

This isn’t an executive position: you won’t have your own washroom, or a seat on the board. On the other hand, you’ll have plenty of money, status, and authority, and unlike your colleagues in management, you won’t spend all day in meetings. You’ll be at the highest level of your profession, and getting well paid to excel at the work you love.

Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do.
—Steve Jobs, Stanford commencement address

What they don’t do

There are a few limitations, though. You probably won’t get to choose what to work on, and you may not agree with all the decisions of the powers that be. In fact, it’s practically certain you won’t. After all, you know more about the subject matter than they do. If, in the end, you can’t live with those decisions, you can go work for another company, but of course you’ll find the same dynamic there.

A senior IC role appeals to those who want to stay technical and keep their hands on the keyboard, or at least the mouse. You don’t have the time-consuming, cross-disciplinary responsibilities of a business owner, or the political challenges of a manager. You get to do all the fun stuff: the building and making. And you can do it until you choose to retire—hopefully in financial comfort.

How to get there

Find out what the situation is where you work. If senior ICs are a thing in your company, talk to them. Ask them for advice. How did they get where they are? What were the steps along the way? And is it what they thought it would be?

Talk to your boss. Do they know this is what you want? What are they prepared to do to help you get it? And what will they expect from you in return? Establishing this dialogue is important, but it’s not enough: you need to keep it open throughout your employment. Check in with them often on how you’re doing, and what more you can do to help them help you.

Don’t wait for annual reviews. A year is too long to wait to find out that you’ve made no progress towards your career goal. Some people blithely assume that if they keep doing what they’re doing for long enough and don’t screw up, they’ll eventually make senior IC.

Well, maybe. But a more reliable strategy is to take personal control of your skills development, and start taking it seriously.

Seniority means mastery

The most senior engineers in any company are the most accomplished, the most experienced, and those who have the most to teach others. If you want to reach this level, you’ll need to become a master of your chosen craft.

Don’t wait for the company to train you. They prefer to promote people who don’t need training. Instead, once you’ve found the craft you love, you’ll need to dedicate yourself to mastering it.

Start seeing your current work not as a simple exchange of your time for their money, but rather as an opportunity to find out what you’re good at, and to get better at it. A professional coach can help you figure this out, support your learning, and keep your eye on the ball.

Manhood is patience. Mastery is nine times patience.
—Ursula K. Le Guin, “A Wizard of Earthsea”

Management

While very senior engineers can be well-compensated, their roles are usually not the most senior in the company. If you want to rise even higher in pay and responsibility while staying within the firm, you may need to think about leaving your technical work behind and switching to management.

Management is perhaps the default destination for many tech careers. Provided you can stay in a company long enough, the natural path to further advancement may be for you to become a manager.

If you don’t change direction, in other words, you may end up where you’re heading. But is that where you want to go?

What does a manager do?

Engineering managers need a solid foundation of technical competence, to be sure, but the work itself is primarily about leading, supervising, hiring, and developing the skills of other technical people. It turns out those are all skills, too, and relatively rare ones.

Managing people is hard; much harder than programming. Computers just do what you tell them, whether that’s right or wrong (usually wrong). Anyone can get good at programming, if they’re willing to put in enough time and effort. I’m not sure anyone can get good at managing, and most don’t. Most managers are terrible.

That’s quite a sweeping statement, I know. (Prove me wrong, managers, prove me wrong.) But, really, would a car mechanic last long in the job if they couldn’t fit a tyre, or change a spark plug? Would a doctor succeed if they regularly amputated the wrong leg? We would hope not. But many managers are just as incompetent, in their own field, and yet they seem to get away with it.

Being a great manager

Good managers, then, like good teachers, are rare, but all the more precious for it. If you’ve ever had a really good boss, you’ll remember them all your life, and, if you’re lucky, emulate them. (You’ll remember the really bad ones, too.) And just because managers don’t cut code or solder chips, it doesn’t mean they don’t have a big influence on the success of projects and companies.

Indeed, managers can have an outsize influence on events. I’m sure we can all cite examples of promising projects that sank without trace because of a disastrous manager. I’m less sure that there are many examples of inspirational managers rescuing doomed projects from the brink, though it does happen.

If you want to become a great manager, which I think is the only kind worth being, start practising now. Learn people skills, communication, collaboration, psychology. Work on understanding the things that make different kinds of people tick. Manage yourself excellently. If you can’t organise yourself, how do you expect to be responsible for a team?

Getting started

Study your own manager. If they do the job well, figure out why (and talk to them about it). If they’re a shambles, figure out what they’re doing wrong, and decide how you’d do better.

A great manager understands what’s happening with each person in their team, and can be there to eliminate problems and roadblocks almost before they happen. Why shouldn’t you start doing this kind of thing right now, rather than waiting to be told? Sometimes the de facto leader of a team is simply the person that everyone turns to when they have a problem they can’t solve on their own. If that’s you, you may already be on the road to becoming a memorable manager—for the right reasons.

Independence

Being independent means working for yourself, most likely in your own company, and maybe with others working for you, but also maybe not. Just being a one-person company doesn’t necessarily make you truly independent, though. For example, are you a consultant or a contractor?

While the client tells a contractor what to do, a consultant tells the client what to do. The difference matters. A consultant is independent; a contractor is not.

The pros and cons of independent working

Running your own business, or otherwise being an independent worker, is great for those who like it. I do, and I was never really happy working for someone else. I couldn’t wait to strike out on my own. I was probably a pretty mediocre employee for that reason, among others. And there was the little nuclear incident, of course.

On the other hand, not everyone wants the hassle of figuring out how to market their business and pitch clients, or the headache of handling accounts and taxes. And not everyone can manage on an irregular, unpredictable income, especially if they have a family to support. You don’t get vacations, insurance, or sick pay. On the plus side, you own a business.

When it’s time to leave

If you do want to swap your stable job and decent salary for the joys of career independence, the transition needs a little careful planning. It would be unwise, for example, to just quit one day in a fit of pique, then start wondering how you’re going to make rent the first few months. Timing is important.

DENPOK: Lao Tzu teaches: the best fighter is never angry. More important than the blow is knowing when to strike. Like, perhaps, after we experience the executive whitewater rafting trip in Coeur d’Alene.
—“Silicon Valley”

And to make money on your own, you’ll need to be excellent at what you do. There’s no one else to pick up the slack. In a big company, you can learn on the job. When you run your own company, you’d better already know your trade.

Testing the waters

If you can make the time, it’s a good idea to dip your toe into independent working by doing a few small, one-off side gigs. You’ll gain experience and some satisfied clients, making it easier to go fully independent when you want to. And if it turns out that you don’t enjoy the experience of working for yourself, it’s better to find that out before you rage-quit your job, isn’t it?

Of course, we don’t always leave our jobs through choice. Layoffs are a fact of life in a volatile industry. You may not see the rocks coming; companies tend to fail gradually, then suddenly. But an unexpected transition to “funemployment” needn’t be a disaster. If you’ve always dreamed of being independent but somehow never quite worked up the courage to jump ship voluntarily, then being made to walk the plank could be just the spur you need.

Making the choice

I hope I’ve encouraged you to think about where your career is going, where you want to go, and what you can do to get there. Of course, you may not yet know how you want to spend the bulk of your career. That’s okay, and completely normal.

But you can think about it, even if it’s too early to come to any firm decisions. And you’re not limited to just one of these potential destinations: many successful careers combine seniority, management, and independence in some way.

For example, you could be a full-time or part-time manager, and also run your own business on the side. Or you could achieve independence by being a roving consultant within a large organisation, while still technically being a senior engineer. Or you could combine all three by being the chief executive and the director of engineering in your own firm. There are many possibilities.

Figuring out who you are

You can inquire of yourself what things you value, and how your working life could contribute to them. As your experience and knowledge of the world grows, ideas may start to slot into place for you about what you want to do and be.

Tell me, what is it you plan to do
With your one wild and precious life?
—Mary Oliver, “The Summer Day”

Your future may not, in fact, lie in the tech industry. That’s all right, too. I have more than one friend who, despite achieving considerable success as an engineer, has decided that this isn’t really what they want to do in the long term.

If you want to quit and be a doctor instead, or a schoolteacher, a spaaaaaace engineer, a woodworker, or simply wander the world like a badass righting wrongs, go to it. Don’t waste any more of your one wild and precious life careering down a blind alley.

Making small course corrections

Once you do have a sense of where you want to go, it can help guide your choices. Even if you don’t know exactly what your perfect job looks like, you may start to feel that you won’t be truly happy until you’re independent, or a senior IC, or a manager. You can steer away from things that would limit your options in those areas, and instead seek out companies, fields, or sectors where you’ll have the best chance of achieving the career you want.

That’s not to say you should have a detailed map of every step that you plan to take (“make junior VP by Q4 2035”). As engineers, we already know that a too-rigid plan rarely survives contact with reality. Instead, assume life will throw all kinds of crazy and unexpected things at you. Plan to be flexible, and to change your plans.

It’s about the planning, not the plan

You can’t stop the waves, as the saying goes, but you can learn to surf. Chance favours the prepared mind. Never underestimate the role of serendipity. The perfect opportunity may show up just when you least expect it, but if you’ve never thought about what you want, how will you recognise it?

The time to start planning for the end of your career is now. It’s never too early, and it’s also never too late, provided, of course, that you don’t have your own little incident. Let’s be careful out there.