Meaningful Careers pt1

Three either/or Defaults

hello! Last week I gave a small "Frank Talk" for my alma mater, Olin College.

One of my goals with that talk was to be a little more open about how career advice is usually about the advice giver moreso than the advice asker. This is particularly a problem as the type of people who give career advice tend to have a few traits in common that don't apply to everyone.

With that in mind, I've been trying to spend more time asking questions to help people get to a good answer for them vs. the one that I'd want.

I've come up with six things I think are worth reflecting on anytime you're planning your next career step. This week I'm sharing the first three - these three are about either/or defaults you probably have. Later this week we'll talk about three types of constraints that can be lenses to help you make a decision.

Work as Purpose vs. Job

I've seen two schools of thought over time:

1. Work on what you love so it isn't work

2. Get a stable income/job so you can do what you love without it being tainted with obligation

I'm more of the former. I love what I do and I think it of it as being one of the core drivers of meaning in my life. I really enjoy talking to people about what they're working on, trying to think through what's interesting about their approaches and, connecting them to each other, reading, writing, figuring out ways to help new stuff exist in the world etc. I do lots of other stuff, but most of my meaning in life comes from work. I'm lucky the thing I get meaning from happens to come with a paycheck. A lot of people who give career advice tend to fall into this bucket because they're willing to spend free time talking more about their career.

Many of my friends take the other approach. Of the three people I see most often outside of Tom, one is back in school half-time doing a second degree in art, one has learned how to do everything from scratch and will save the five of us in the apocalypse (I hope), and one has a set of hobbies so elaborate that I started calling it the "triple C" (cycling, ceramics, cooking). For a long time, I felt pretty insecure about this. I assumed my lack of meaning from things outside of work said something bad about me.

Neither school of thought is "right.” They both have upsides and downsides.

If work is your main sense of meaning, you can be set up for some extremely rough downturns when things don't work out. I’ve had periods of six months where I couldn’t get motivated to work on something new.

If it's not your primary purpose, it means you might be spending 40 hours a week on something you don't really care about.

Neither path will inherently make you more successful. I’ve seen plenty of people who don't view work as their primary purpose but have very successful careers. Even though there's no right answer, I think most people tend to have an innate pull towards one or the other and it's worth considering which you are.

Two questions that can help you figure it out:

1. If you knew you had enough financial resources for X time period, what would you do? This isn't about "if I had a two week vacation" - more if you had a year or even the rest of your life to do something, what would be interesting?

2. The last time you had free time for a long period of time, what did you gravitate towards? Again, this shouldn't be "when I was burned out I sat on the couch for two months" (that's fine too! I've done it!) but after you have recovered, what do you do with your time?

One place that people sometimes end up at is wanting to sequence the two types of careers - "I will work a job for X long, and then once I have enough I will switch to spending time on my purpose." For this case, I strongly recommend outlining what "enough" is and at what precise moment you'll make the leap. It's easy for that to be a moving target and end up ten years down the line without "enough" and still doing something you don't love in a work pattern that doesn't fit how you want to work.

Another one I've heard is from people in either boat who still feel like, "I have a job and it works well for me/gives me individual enjoyment, but I worry I'm not doing enough good for the world." A school of thought I recommend here is the idea of Effective Altruism - often, if we have a thing we enjoy and provides income, we can do more good by giving our financial resources instead of switching to something that's "more hands on helpful."

Yes vs. No

Another common pattern I've seen is that some people tend to default towards yes, and others default towards no.

1. This Derek Sivers article is often a touchstone telling the yes people to tone it down.

2. On the flip side, a recent book on trying to shift no into yes was Shonda Rimes's Year of Yes.

An easy way to discern which you are is to consider the last few invitations you've received. You probably barely think before going into one of your patterns, but you likely have a subconscious tendency to either justify why you should do it, or why you shouldn't do it.

I'm a yes person (again, people who end up giving career advice talks are often yes people). Saying yes allows for a lot of serendipity. I also superstitiously believe saying yes to opportunities means that more opportunities will come along in the future. I think that saying yes to Accomplice's Rev program in 2016 led me into angel investing, which led me into my current job. All of that feels like it links back to the first yes.

The downside is that saying yes takes time and energy away from other efforts that you might have chosen for yourself. I did a little analysis recently and on average I'm pretty sure I spend about three hours a day on things that happen to come up because I indiscriminately say yes. That's not free - perhaps if I'd said no to Rev, I would have found my way into angel investing in a different way, or found something else that I find even more fulfilling (I doubt it, but you never know). I think that yes was worth it, but there's others that cost me time and energy and weren't.

Always saying yes can leave you with a feeling of "the grass is greener" - if you say yes to exploring every possible new job that comes along, you'll always end up feeling like a better role might be out there vs. settling into what you have and making the most of that work.

If you default to no, you're a master of your own time. You'll have a lot more space to generate internally "what do I want to be doing right now?" and make that happen. It likely leaves more time for focused work. It also leaves you with more leeway to only do things that fall into your Zone of Genius - whereas other people are apt to ask you to do things all across the spectrum. I occasionally end up saying yes to things where I'm actually bad at that thing, and someone else would have been a way better fit (if you need an example of this, ask me about the gift committee). Default to no people don't have that problem!

The downside of defaulting to no is that you can miss out. If you never consider new opportunities, you might stay too long in a job that isn't a good fit for you, or not have a breadth of opportunities to draw from when you're exploring what can be next for you. You might have had a great time at an event but your default made you say no before really thinking through what it could do for you.

There's nothing wrong with either way of looking at opportunities, but it's certainly worth knowing which one you are and keeping that bias in mind when you consider something new.

Upside Maximize vs. Downside Minimize

This is the axis I hear people explicitly talk about the least when they're making a career decision. This is tightly coupled with risk tolerance, but I think this framing is a little more clear as a default pattern.

1. An upside maximizer is looking for opportunities for growth, and what "could be?" When they're considering going to a startup, they're more likely to think "what are all the things I'll learn on my way to our IPO?"

2. A downside minimizer looks a lot more at risk. When they consider joining a startup, they're thinking "what would happen if this startup fails?"

If you already read this newsletter and made it this far, it'll come as no surprise that I am upside maximizer. When I wanted to work at Kickstarter because I thought it'd be awesome to do the job version of the Awesome Foundation, I completely ignored all the downsides (massive pay cut, move to a city where I knew very few people, possible end of a long term relationship) and figured "it'll all work out, this is going to be AMAZING."

The temptation of the upside overwhelms the risk of the downside for the maximizers, the possible loss might prevent the downside minimizers from making a leap. Of course, both people are going to be able to weigh both sides of the equation. But people tend to experience one side or the other as a larger emotional experience. Part of this will also relate to their resources and constraints, which we'll get into next week. Part of it may also be about how bets worked out before - if you've ended up in a few bad work environments, you'll be more cautious about picking the next one.

I encourage downside minimizers to think through "what's the REAL risk?" - many downside minimizers have enough financial and career security that a failed startup would not be a big deal, and the base emotion can prevent them from taking a cool opportunity.

For upside maximizers, I tend to focus more on "is there another way to get you to the same thing?" - sometimes the first awesome opportunity can be changed or replaced with something equally valuable that can also minimize downsides.

Tying the Three Together

I don't think there's any reason to change your default orientation on these three axes. If you're around a set of people who trend one way (or speakers who are all purpose/yes) you might feel like you're out of place, but people end up in every permutation of these sets of factors and have fulfilling careers! The key is knowing your biases and being able to take those into account as you work through a decision.

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Since I've only talked this through with one group of people, I'd love to hear thoughts. Do these categories resonate with you? Do you have others you think of as being classic dichotomies in how people think about their careers? Hit reply, I'd be happy to hear from you!