Who do you want to be? Three principles for shaping a career

A small percentage of people have a clear idea of what they want to do in their careers. You know the type: they’ve wanted to be a surgeon since they were five, and surgeon they are. The rest of us grapple with the question and its derivates, such as: How do I figure out where I want to be going? How do I grow in my career? What options do I have if I hate my current job or function? Do I take this offer that came out of nowhere?

In my experience, it’s undesirable to have 100% certainty of what you’ll be doing for the next few decades: it makes you believe that it’s possible to follow a plan you laid out X years ago and it closes you to opportunities that arise along the way. I also find it unhelpful to have no idea: smart tradeoffs become more challenging and it may lead to your running from unhappy setups in random directions.

My current approach is to apply broad principles to give my career general shape, then be as aware as possible of my current state, opportunities, and challenges so I can make local-level optimizations. Below, I cover the three principles that retrospectively have worked well for me.

It’s not like I’ve had this clarity from the beginning: I’ve picked these learnings up on the way and I keep adjusting this mental map. I’d love to hear what frameworks you apply in thinking about your career!

Life goals > career goals

I deliberately titled this post “Who do you want to be,” not “What do you want to do.” The two questions are often conflated, yet there is an important difference. What you do is a subset of who you are; how you experience the world and what you bring to it are not equivalent to the work you produce. Our careers should be in service to our lives, not the other way round.

Naturally, designing your life is an order of magnitude harder than tackling career design, but what good is achieving a career goal if it doesn’t help you with your life goals? A whole literature exists about people getting to the summit of their field and yet finding themselves unhappy because they’ve maximized the wrong things. Many of us know people in this position; some of us are on this path today.

I don’t know of a fool-proof way to prevent this kind of disappointment, but I do believe that grappling with the question of what’s important to us in life is a worthwhile exercise.

Let’s say that through introspection you conclude that you value status in society. That alone doesn’t define your career for you, but it helps you think about career goals that earn status, e.g., becoming a judge or a CEO. On the other hand, if achieving financial independence by 30 is important to you as a way to choose how to spend your days, you might want to focus on a career that optimizes payouts early and doesn’t take dozens of years on average to recoup your investment (so pick sales over specialty medicine, for example).

This line of reasoning can be applied at any point in one’s career: new parents often re-evaluate their approach to life-work balance; I’ve become a lot warier of working 60+ hour weeks in my mid-thirties.

Here are some practical tools I’ve found helpful in figuring out what I want out of life:

  • The appendix of First Things First has a guide for developing a personal mission statement. I realize it sounds highfalutin, and yet it’s one of the most clarifying exercises I’ve ever done.
  • Designing Your Life walks you through the whole process, as the name implies.

I came to value this type of inquiry at 32, with nine years of work experience under my belt, driven by a professional crisis that made me re-evaluate what I was good at and how I wanted to spend my time. I don’t know what answers I would’ve come up with had I asked myself these questions earlier. I do know they would’ve been different because I’ve been adjusting and updating my mission statement continuously. While the answers change, I find it comforting to have an answer to “who I want to be” at any given point, an answer I can lean on to help me figure out my career goal.

Before I’d done this self-inquiry, my long-term career goal was to be a COO or GM of a high-growth technology startup or business unit of a company. My career path sure looks like it’s been going in that direction. I’ve since realized that this goal contradicted with my life goals of independence (i.e., directing my focus), physical and mental space around me, and going for quality over quantity and speed. I now see myself running my own small bootstrapped business/startup in the future.

The point of thinking through your life goals isn’t to define them once and for all; it’s to get in touch with what’s important to you at a point in time in the most zoomed-out sense possible and to see the answers evolve as you acquire new experiences and information, as your circumstances change, and as new opportunities present themselves.

Long-term dream > immediate next step

Even if you’ve figured out your life goals, that may be insufficient to help you with the typical career choices:

  • Should I stick it out at my current company so I get the promotion in 6 months even though I kinda hate it here?
  • I took a recruiter’s call and now I have this offer; should I take it or stay where I am?
  • Should I get an MBA?

Trying to answer these questions without putting them in perspective of your long-term career dream is likely to lead to micro-optimizations that may or may not get you where you want to ultimately be going.

A long-term career “dream” is ideally something very concrete, to the point of “role X at company Y,” for example “a COO of a 400-1,000 person tech startup.” The precision, while obviously suspect, helps you define the kinds of skillsets, environments, and networks you want to acquire to actually get there. It allows you to start doing something about your long-term career dream right away and to make thoughtful decisions about the questions above.

Here are some practical tools I’ve found helpful in thinking about long-term career dreams:

  • I’ve found this sweeping and data-based overview of problems facing humanity fascinating. It hasn’t resulted in massive shifts in how I think about my career, but I can see how it very well could for others, especially those earlier in their path.
  • I like using the process of elimination. I know, for example, that I don’t have the interest/aptitude combination to be a doctor, artist, scientist, or engineer; my long-term career dreams reside in the business sphere. This approach works better, I find, for folks who have at least a few years of work experience and have thus learned a bit about what they’re good at and what interests them.
  • About two years ago, the question of “Who do I want to be when I grow up” came to the fore with renewed strength for me. My coach David Klemenz gave me the following prompt: “Write down a list of things you like or find cool.” I was skeptical at first. “I mean, I like cats,” I said. He told me to record that. Next to cats appeared human progress, independence/autonomy/self-reliance, quality and depth, and so on. I used the resulting document as a checklist at a career cross-roads a few months after creating it. It helped me pick a non-obvious option and turn down a very interesting and lucrative offer. And cats are now featured prominently on this blog. 🐈 If you’re feeling blocked, start with a long list of things one can value in life and circle five that resonate with you the most:

Just as your life goals will change over time, so too will your long-term career dream. As you progress through your career, you’ll learn more about what makes you tick and new experiences will give you new ideas. Expect to update your long-term career dream multiple times.

Skillset range, dynamic environments, and powerful networks > titles and clean lines

When evaluating career options, it’s often more comfortable to optimize for criteria that have immediate validation, like titles and clean progression within a job family. While there is nothing inherently wrong with these, I think there are more valuable and less obvious factors to consider. They require some faith ex-ante because their benefits tend to materialize years later.

I’ve learned to optimize for skillset range, dynamic environments, and powerful networks. Here are some examples from my career to give more color on each:

Diversify skillsets

Management consulting has been an amazing asset for me in this regard. It was my real business school, much more useful than the actual MBA. The three biggest skillsets I took away from consulting are 1) how to structure problems, 2) how to power through to the answer, and 3) how to communicate effectively. I’ve used these daily in each subsequent job, and they’ve helped me tremendously. I still can’t quite believe I got paid to learn them, essentially.

People and org management is another transferable skill I’ve acquired. Its constituent parts, e.g., operating cadence, performance management, career development, are applicable in any management role.

The best tool I’ve found that lays out all the possible competencies one can exhibit in the workplace is the Leadership Architect sort cards and accompanying book from Korn Ferry. You can use it to decide what competencies you’d like to acquire that’ll help you get to your career dream.

Problem-solving and people management are examples of competencies one can have in the workplace which, to me, are a subset of skillsets. Another subset is the types of environments you can be effective in.

For example, I’m on my third “career” in my 13 years of work experience. The first one was in strategy, the second in startup operations management, the current one in advising and coaching. Recruiters tell me that my range of strategy to operations, B2C to B2B, and company size is unique: apparently, the supply of people like me is smaller in Silicon Valley than the demand. Especially as applied to high-growth startups, which can double+ once a year for a number of years, having this kind of versatility is an asset as, presumably, it means I can help folks see around the corner. For me, the benefit of this versatility is worth the cost of a somewhat limited depth of expertise in any one of these areas.

To be clear, I haven’t set out to collect this variety of experiences; it’s happened naturally. I have, however, deliberately avoided “doing the same role multiple times.”

My advice is to not be afraid of diversifying your skillset with “random”-seeming opportunities. For more inspiration, rewatch the “connecting the dots” part of Steve Jobs’ Stanford commencement speech.

Pick dynamic environments

Dynamic (i.e., high-growth) environments beget opportunities for learning and advancement. Think California during the Gold Rush or pre-IPO Google.

I’ve made a few lucky choices in my career that have benefited from this effect:

  • A year into my management consulting job in New York, I took the opportunity to do a year in a developing office, Moscow, as part of BCG’s global rotation program. I knew I was going from a 400-person office with established processes to a 40-person upstart that was short on middle management, likely chaotic, and whose office had just, no joke, been through an actual fire. The benefit was much higher levels of responsibility given tenure. Coupled with a booming demand for management consulting services in the Russian market at the time, this created a career growth flywheel. I stayed in Moscow for another 5 years, including a switch to a corporate strategy role at a client that I still can’t quite believe. The labor market was such that I was made a Chief Strategy Officer of a national telco ($9B in revenues, 65M customers, 25K employees); I was 28. A number of my colleagues went on similar trajectories. This doesn’t happen in stable, low-growth environments.
  • I’m very happy with the conscious choice I made to work in the Bay Area startups for my second career. Silicon Valey has been one of the most dynamic environments globally over the last decade. The supply-demand imbalance for qualified labor this has created has meant that just by virtue of being in the right place at the right time I, along with others working in the Bay Area, have had access to a disproportionately large set of high-quality career opportunities.
  • When transitioning to startups in 2012, I was in the fortunate position to join Google (30K (?) employees) or Dropbox (200 employees). I picked the latter based on the energy level I felt there. The opportunities for growth I subsequently enjoyed at Dropbox were quite special. The beginning smaller size and crazy growth rate contributed to this, as did Dropbox’s culture of giving a lot of responsibility to hungry folks who didn’t have deep functional expertise. I did a (de)tour of duty in customer support and revenue retention, which was an incredible learning experience that allowed me to own business metrics and learn people and large org management rather early on in my career. Did I know Dropbox would turn out so well for me? I didn’t, of course. But regardless of its outcome, this was a good bet.

My advice for picking dynamic environments is to consider recent growth rates in the place/company you’re considering and think through the driving forces behind them. One way to derisk stepping into high-growth situations is to take their current scale into account: it’s easy to show crazy growth from a very small base and much harder to do the same from a reasonably-sized base.

Seek out powerful networks

Associating with large numbers of quality people has, in my experience, the highest multiplier effect on future career opportunities. I say “multiplier” because quality people are likely to continue joining powerful networks in the future, growing your opportunity set by virtue of their knowing/thinking highly of you. These networks (e.g., companies, schools) pay dividends in career and business opportunities years and decades into the future.

I’ve been part of both strong (large and high-quality) and weak (small, low-quality, or both) networks, and the difference in payback has been material. My strongest networks come from three excellent companies. They consistently create career and business opportunities for me. For example, 100% of my consulting work (my current focus) has come to me inbound from former colleagues.

My best advice for getting powerful networks to work for you is to:

  • Pick them well. The best way to do that is to meet as many people during the interview process as possible and critically assess their raw horsepower, curiosity, and fit with your values. You’re interviewing them as much as they’re interviewing you. Make the most of it.
  • Do a great job once inside. While you will never be liked by every single person you meet, an obvious no-regret move is to generate a strong group of supporters through high-quality work and treating people well.

To recap, these principles for thinking about careers have worked well for me:

  1. Life goals > career goals
  2. Long-term dream > immediate next step
  3. Skillset range, dynamic environments, and powerful networks > titles and clean lines

I’d like to leave you with this thought: don’t postpone becoming who-you-want-to-be until you figure all these things out. If you want to help people develop and you’re currently an individual contributor, mentor others or start an internship program. If social outcomes are important to you, start or join a movement. If you’re after business impact, start a company or a side hustle.

Take steps towards being who-you-want-to-be today.

This Post Has 4 Comments

  1. Well done! This reinforces so many of the points you brought up on our recent conversation. I noted that you are also a fan of the career architect card set – I have been using them for developmental discussions for many years.

    1. Thank you, Tim! Yes, Career Architect is the best investment, like, ever. I’ve also used it on myself and for putting together job reqs. So good.

  2. This is a great post, Olga! Totally agree with everything you have here. Random anecdote on your point on “powerful networks”. When I was graduating from college, I asked my advisor whether I should work at a startup (since I thought I might want to start a company at some point) or whether I should work at a larger company to understand what a startup aims to become. Even if the framing of the question probably wasn’t quite correct, his answer was that it didn’t matter. What he thought mattered most is that I should work at a company that had the highest quality people because they would then go on to do interesting things in the future. I didn’t follow that advice for my first job, but I did eventually figure out the truth in that advice, and have since passed along the same advice to others who are earlier in their careers.

    1. Thank you for sharing the reinforcing story, Alex!

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