How to Think About Your Career

If you had asked 22-year-old me what my “career aspirations” were, I would have looked at you blankly and then casually changed the subject to what programs you’d recommend to model cute 3D bunnies for a video game, or whether the writers of Alias would be so devious as to ship Sydney Bristow and Sark. It’s not that I didn’t think about my career at all. I was ambitious — I wanted to be a part of something big. I wanted to be able to support myself financially and not worry my parents (as this was a high bar set at doctor, aka the “stablest of all professions,” I suspect they still secretly worry about this.) I wanted the kind of job where I wouldn’t be watching the clock every hour, daydreaming like Rebecca Black about Friday.
But beyond that, the specifics of “thinking about my career” was a giant grey cloud to me. It felt almost icky to be too career-oriented, like if you were, you were that kind of self-absorbed person constantly trying to game the system by sugar-coating the things you said to your bosses. Besides, at 22, I had taken my first job at a start-up where we were moving way too fast to sit down and idly contemplate the skills we hoped to learn. Who needs career conversations when you’re busy changing the world?
Here’s the thing though: your career, like your life, moves forward whether you think about it or not. If you don’t think about it, then you’re putting faith in the winds. Maybe you’ll end up somewhere you’ve always wanted to go. Maybe not. Why take that chance when you can captain your own sails?

Here’s what I wish I had known about getting a handle on my career earlier in life:

Your career is defined by your skills and how you’ve used them, not by any external measure of your progress.
It’s common to think of your career as your level within the company, or how much money you make, or your title, or whether you were included in some prestigious group (a meeting of importance, an exclusive conference, a list of N under N, an award recipient, etc.)
Often, I hear people say things like, “I’m interested in advancing my career. What do I need to do to get promoted?”
This is a perfectly valid question to ask, but I suspect what lurks beneath the question is the assumption that advancing one’s career = getting a promotion. I contest this quite heavily. In my opinion, it’s like equating being a good friend with getting invited to friend’s wedding.
Certainly, the people who attend someone’s wedding are likely to be good friends. But you wouldn’t think that optimizing for getting an invitation to a wedding is the right way to go about being a good friend. In fact, it’s entirely the other way around. If you focus 100% on being a great friend to someone, even if you never once thought about being invited to their wedding, guess what. You’re probably going to get that fancy envelope in the mail.
The same is true regarding your career. If you focus exclusively on improving your skills and your impact to your organization (or to the world at large), the promotions, raises and accolades tend to come as a byproduct.
The reverse isn’t true. As an extreme analogy, you might have a terrible boss who tells you the way to get a promotion is to shut your mouth, fetch her coffee every morning, and do any busywork she assigns you. Now, maybe you check off these boxes and get a promotion. Cool. But would doing this actually help you in the long run? Would doing this teach you new skills and make you a more attractive hire for some other company down the line? Probably not. Maybe what happens is that you rise in the ranks of that company only to have it go bankrupt later on. (Hey, this isn’t unreasonable given the organization seems to possess questionable management practices). Post-bankruptcy, you realize you don’t have many marketable skills in this rapidly-changing economy, so it’s hard to get a job at a similar comfort level to what you had. Life sucks. You get bitter.
So don’t ask “What does it take to get a promotion?” Ask instead: “How can I be doing more to help make our customers (or would-be customers) happy?” Ask “What skills should I be developing to help me increase my impact?”
Even if your current company has a broken promotion system, even if your company collapses tomorrow due to the winds of ill fortune, even if every external measure you hold yourself to — title, salary, affiliation, awards — goes out the window, your skills are forever. Nobody can take those away from you. No matter where you journey, your skills and your past experiences go along for the ride. This is why you shouldn’t worry too much if your career doesn’t follow some up-and-up external ladder structure. Are there instances where a new role with a pay cut and a title downgrade might unlock a treasure trove of new learnings and opportunities? Of course. Might you be better off in 10 years if you take a smaller position at a faster-growing company? Just ask Sheryl Sandberg.
Careers are long, so invest into them where it counts.

Treat your manager as a coach, not as a judge.
For most of my career, I had the mental model that my manager, like my teachers and professors of the past, was someone in a position of authority who took note of what I did and passed judgement on it. They determined whether I was or wasn’t doing well, what I needed more critical feedback on, and what letter grade or assessment I deserved.
As such, my modus operandi for interacting with my manager could be summarized in one neat statement: don’t come across as an idiot.
This meant that I’d try and act as if I had my shit together in front of him or her. I’d exude confidence and optimism, even when I wasn’t feeling it. I’d say “Oh, I’ve got it under control,” when they asked if I needed help with anything. There was no clearer evidence of personal failure than if my manager had to get involved in something I was responsible for. I read it as a neon sign brightly flashing Warning: employee not competent enough to take care of this task on her own.
It wasn’t until I had managed for many years myself that this mindset began to change.
Look, your manager’s job (assuming she is a good manager) is to help you and the rest of your team get better results. From this perspective, it is completely logical that she should be invested in your career. When you do better, then by extension, she does better. Hence, your manager is someone who is on your side, who wants you to succeed, and who is willing to spend a good deal of time and energy to help you do that.
Can you imagine a star athlete trying to hide their weaknesses in front of their coach? Would you tell your personal trainer, “Oh, I’m pretty fit, I’ve got it under control” when she asks you how she can help you achieve a better workout? Of course not. That is not how a coaching relationship works.
It’s precisely because I didn’t see my manager as a coach that I missed out on years of asking for and receiving training and feedback that would have helped me become better faster. Yes, of course, your manager still plays the role of judge. Yes, she can (and should) fire you if you can’t do the job, or do nothing but play Pokemon Go all day. But assuming you’re not unqualified or lazy or an asshole (and trust me, if you were, you’d know quite quickly), then your manager would like nothing better than for your career to be on a rocket-ship trajectory to the moon.
You don’t just need coaching when you’re struggling. I’m willing to bet that everyone who’ll take home gold at Rio will have a coach. A majority of them will probably credit good coaching as a critical factor in getting them to where they are.
The more honest you can be with your manager about your aspirations, your motivations, and where you’d like their help to improve, the faster you’ll move.

Create a mental image of yourself mastering the skills you most want to master, and believe that that is in your future.
A few years back, I wrote about a little book that caught my eye at Safeway, an obnoxious little thing with faux wax seal, quill-pen script, the ancient parchment paper glowing as if with magical beams. The book loudly proclaimed: Get whatever you want. Discover the secret to life.
Spoiler warning ahead, but this is what the secret to getting whatever you want turned out to be: if you believe it can happen, it will happen.
(I know, I know. I too was hoping it would be something more along the lines of Burn a sprig of Douglas Fir at 11:23pm on the eve of the New Moon and bow three times to a fat armadillo.)
As trivial as the new-age tidbit of if you can believe it can happen, it will happen sounds, there is research that shows if you can create a clear visualization of yourself achieving the outcome you want, you prime yourself to act in a way that is consistent with what you imagine.
Many years ago, when I was frustrated by all the things I struggled with and felt unequipped or scared to do in my job, I started a list of what I wished a future me would one day be able to waltz in and easily accomplish. This list is titled One Day, I will…
Now, maybe seven or eight years later, this list is still up-to-date. I’ve added additional items throughout the years, but the more incredible thing is how I’ve been able to check things off. The skills that once seemed a distant dream when I was 25 or 26 now feel like second nature. And these proof points give me confidence that all the new items I am still adding will also happen. In 5 or so years, I’ll look back feeling great about having mastered those skills as well.
Going back to this list a few times a year gives me a deep sense of motivation and comfort. These things I can clearly visualize are totally doable. So do them I will.
If you’re curious what my list looks like, here is a snippet of items checked off through the years, and items that I am still working on:
One Day, I will…
…
✓ Not feel intimidated when I interview someone because I’m worried about what they think of me as an interviewer.
✓ Not be nervous about a public speaking event in the days before it happens.
✓ Feel comfortable speaking up in a meeting of > 5.
✓ Publicly blog without stressing about what other people will think.
Succinctly and clearly be able to make the point I want to make in 3 bullets.
Regularly be able to weave compelling stories and analogies into verbal explanations.
Host large events where people have fun and I am not really stressed out.
…

You own your career, and you have more of an ability to shape it than anybody else.
This is the last takeaway because no matter how many people are on the sidelines helping you, ignoring you, or working against you, your career — like your life — is your responsibility. Don’t blame your manager, your significant other, your friends, or your company if you don’t have the career that you want. All of these things are in your power to affect or change.

• If you find it hard to wake up excited about going to work in the mornings, ask yourself why.
• If you look back on your last six months and you can’t point to anything that’s been hard for you, question whether you are challenging yourself enough.
• If you find yourself constantly looking for other people to tell you how awesome you’re doing, consider if you’re shortchanging your own growth and development.
• If your manager is not giving you the support or coaching you’d like, tell her how you’d like to be supported or coached.
• If working at your current company is not aligned with your long-term goals or values, consider making a move.
• If you’ve never thought about where you’d like to be in three years, sit down and think about it.