The Angstiest 1 on 1 Question

I do a lot of 1 on 1's with young professionals and the question that seems to prompt the most angst and anxiety is:

"Where do you want to be in 5 years?"

It's honestly become such a cliche and trope of a question now that if you ask it, the person you are talking to will have answered in their heads, "not where you are, manager-bot."

In my experience, there are actually some people who know the answer to this question and can answer it precisely. For example: "I want to be an early engineer at a tech startup focusing on the environment." Or, "I want to lead a large team at a FAANG company and take my learnings of big organizations into empowering diversity at scale."

I'm very happy for these kinds of people and they make my job very straightforward and the whole time I'm jealous of how their brains work. Watching them talk about their career is like watching someone drop a pin on Google Maps and then hearing a robot voice say "calculating route."

If you're like me, and you don't know how to answer that 5 year question, even if they change the horizon to "1 year" or "10 years" - you are not alone. I think of the hundreds of professionals I've worked with, interviewed, coached, and I'd say 95% do not have an honest answer to that 5-year question. I say "honest" answer, because there was a time when that question was so goddamned popular you had to have a fake answer prepared so that you didn't seem like an idiot. That's not to say that those people never figured out the answer to their "5-year" question, it's more that it can be elusive. Really elusive. Not only that, but when it comes to figuring out what work you want to do, there's a huge difference between "knowing" and "knowing-by-doing". Basically, you can't think yourself into knowing what you want, you actually have to do the thing long enough to figure out if 1) you actually like it or 2) oh hell no. It's tacit knowledge. (Hermina Ibarra wrote a great book about this called Working Identity if you're intrigued.)

So what is this blog post? A gigantic treatise on how I think planning is stupid? No, absolutely not, and please no need to shove that Dwight Eisenhower quote at me, I know it. I understand. I like plans, really.

I'm just saying, sometimes we need another way by which to navigate our lives other than knowing what we want to be 5 years in the future. Or, perhaps we picked a 5 year goal, but somewhere along the path things felt ...off... and we need to re-orient. And we don't have a different 5-year goal to orient towards yet. Or maybe we just want to explore because we don't trust that the destinations we have been shown are the only ones out there.

The good news is there are other ways to navigate that don't require a 5-year goal, or a google maps pin on a destination. What's worked well for me is navigating based on values and commitments. Think of it like navigating by compass or star position with no specific destination in mind (yet).

Let me give you an example of a decision that I made that seemed really flippant at the time, but was actually me navigating by values. If you don't know my backstory, I made my career by being employee #9 at AppNexus, a tech startup in NYC. I had met the founders of AppNexus via RightMedia, another startup in NYC. RightMedia happened to be my first job out of grad school. A question I get asked a lot is "how did I know which company to work for out of school?" I want desperately to tell everyone how strategic I was about my choice, how I had done all this research about the most promising startups in NYC, how I knew that New York's tech scene was poised to blow up, how I deduced that I would get more exposure to tech infrastructure at a small shop versus a bigger one. I wanted to give people what I felt like usable, bulletproof advice. Like "know where you want to be in 5 years, then work backwards" advice. But the truth was I made that career decision based on a few throwaway lines in the bio of the CTO on the company's website. His bio said that he enjoyed playing intramural basketball with his colleagues, and then it linked to a picture of the team, and the picture was too poorly lit and poorly framed to have been purely related to PR. This silly picture is what I based one of my big career decisions on.

I had better offers from bigger companies, better titles with more money, but all those interviews left me with a distinct feeling that I would be working alone. So I had no idea what "adtech" was let alone what an "optimization analyst" would do, but I thought, at least I could join their intramural basketball team. Older-me now wants to throttle this younger version of me a little bit... because ...she's ...so ...unstrategic, WHY?? But the truth is - that ended up being a great decision. One of the best decisions of my life.

It could have been sheer dumb luck, of course. (You'll find that in the startup world sheer dumb luck accounts for quite a lot.) But let me tell you what wasn't dumb luck: that innocent wisdom in my younger-self that somehow knew that teams matter more to me than almost anything. That I am at my very best when I have a team to show up for, and a team that shows up for me. Tapping into that "teams" value was the reason I had the emotional endurance for the startup gauntlet. If I had picked a job out of intelligent strategy but not one that tapped into my commitment for teams, there's no way I would have worked as hard.

So I think there's a lot of wisdom that can be had in navigating by values, and frankly, even if you had a rock solid 5-year plan you should still learn how to navigate by values. (Especially if the GPS on your 5-year-goal does you dirty and leads you somewhere dark and shady and not at all on your roadmap. It happens.)

How do you come up with your values? Honestly, that can be a whole separate post, but my suggestion is to do what I learned from Lauren Borden which is to search for a word bank of values (like this one, or this one) and whittle it down to five (JUST FIVE) that mean the most to you right now. "Don't overthink it!" she would say (which is ironic b/c she's a big-ass overthinker herself). Once you narrow down to your 5, come up with a commitment you have for each of those values. The commitment should be concrete enough that you can navigate a decision with it.

For the sake of example and massive vulnerability, here were the results of my exercise:

Values: Dependability, Teamwork, Expression, Excellence, Community

Those sound pretty cool and all, like they would make nice tattoos if I turn them into kanji (kidding kidding), but they are not very easy to use for decision making. So I take it one step further and ask myself, for each one of these values, what's an example of something concrete I'm willing to do to commit to them? Here's what I came up with:

I'm committed to supporting under-served communities and leaders. (Community)
I'm committed to being an all-weather friend. (Dependability)
I'm committed to the craft of leadership as a vehicle of service and not ego. (Teamwork)
I'm committed to excellence, it's an honor to be able to give your best everyday. (Excellence)
I'm committed to the art of storytelling. (Expression)

I mean yeah, it's hardly the 10 commandments or the Rosetta Stone. But it doesn't have to be! It just helps you make choices. You know you got it right when you read it and you feel a sense of sturdiness in your soul. Like yeah, the wind might be blowing to the East but I know I have to head West, and I don't care how windy it is because I am sturdy. Know what I mean? (For the record - if the sturdiness ever decreases, you can and should tweak and tune these commitments. We're allowed to change.)

So if the "where do you want to be in 5-years?" question gives you some existential angst, don't fret. Think a little about where that question really came from. My gut says that question is more about companies trying to screen out people who will leave in two years rather than it is about helping people navigate their career. There are other ways to navigate. Build yourself a compass that you trust.