Meaningful Careers pt2
Real Needs, Unusual Tolerances, and Timelines
Last week I shared three dichotomies you can consider when choosing your next career step:
Purpose vs. job
Default to yes vs. no
Upside maximize vs. downside minimize
Of course, this leaves out a lot of other pieces of the puzzle. Today, we're going to walk through the three other pieces I encourage people to consider.
What do you REALLY need?
Most of the time when people are writing down what they want out of their next career move, it reads like a laundry list of nice-to-haves and tradeoffs. That's fine to do, but I recommend instead getting really honest with yourself about what support structure you actually need in order to do your best work. I consider these the absolute non-negotiables.
This might be about living in a specific place, or near specific people (family, friends). It might be about a commitment to a morning routine, therapy, exercise, or a hobby that allows you to take your mind off work. It could be about a certain income level to sustain your lifestyle. It could be about access to clothes/accessories/fashion that helps you feel your most impactful. It could be about reaching a threshold where you feel a sense of security that even if you take a risk you won't end up missing rent. It could be a combination of these things! The good thing is this can really help you limit which opportunities you consider so you can focus on the ones that might fit.
The top of my list is pretty simple. I've been able to take a lot of risks because I have a narrative in the back of my head that goes "well, you could always go stay in your parents basement for a couple months and sort it out." People find that one odd, but in summer 2020 I actually did it! It helps me a ton with effectively being able to YOLO, especially when I want time between roles.
I also tend to need someone who can help out when I overcommit (usually Nikki or Tom). I need to have a quiet space to work in, and some time to be alone and read. Beyond that yes: therapy, exercise, and close friends nearby sure make my life a lot better. But if I don't have the sense of security, the constant backup support, and quiet space, most of what I do wouldn't happen.
Lying to yourself about these doesn't do anyone a favor. Twitter is really judgmental about which of these you "should" or "shouldn't" need, but at the end of the day not everyone needs the same stuff to be productive. You might have ones I've never thought of. Just figure out what they are, and what's a need vs. a nice-to-have.
What will you put up with that others won’t?
The other piece that's more useful than "nice to haves" is the "I'm willing to deal with" list.
Everyone has unique things they don't mind (or even enjoy) that most other people hate. Again, I'm not going to guess all of these. You could be happy to deal with technically pedantic (but brilliant) engineers. You might be willing to work 80+ hours per week. You could be willing to travel Monday-Thursday. You could not mind interviewing a ton of new people. You could not mind sending status emails. Whatever these things are, they're a key to where you might thrive or have a unique advantage.
I like having full schedule control, but as long as I feel like I have it I'm happy to take a meeting on a weekend, evening, early morning, etc. I'm happy to have hard and direct conversations all day long if I don't have to send boring status emails. There’s other ones I did earlier in my career that I no longer will.
Chances are these things won't feel particularly onerous to you because they aren't a big deal for you. Do you ever talk about a thing at work and people think you're complaining or go "ugh that must be horrible" but that never crossed your mind? That might be one.
Another easy way to find out what they are is to ask your friends or those you've worked with before. Is there anything you do where they're surprised at just how smoothly it goes? That's all worth looking at because it’s a competitive advantage in getting roles that require it.
How will you know when to make a change?
The third piece is figuring out "when does it make sense to re-evaluate the decisions I've made?"
Especially early in your career this can be hard to do. In school, you usually get new classes every 3 months and an assessment period. You have set milestones. At work, there may or may not be timeline(s).
For example, at a big company you might have an annual review cycle, a weekly 1-1, and stock vesting monthly. It can be hard to pick the right time amongst all of those to assess how you're really doing, what you want to learn next, and when might be the time to make a leap. The flip side is when it can feel like there are no real breakpoints and things just keep going.
Most of the time when you're starting something new it helps to put something in your calendar, or use a service like Futureme.org to remind yourself of what you were considering. It's always okay to change when you re-evaluate, but it's good to know when to do that by. I like to write it down so I don't have to run a background job to self assess all the time. I wouldn't want to be surprised 10 years down the line with "oh I guess I'm still here" - staying somewhere 10 years is great, doing it without thinking seems less so.
More tactically, it’s important to get the cadence right. If you're early in your career at a big company, and know you can't be promoted for a year it's probably not worth checking in every week on when you get be promoted (yes I did this, sorry Rajesh). Waiting and being surprised probably isn’t right either. Quarterly might be.
If you start a job saying "this will be a bridge to X" it also makes sense to know when you were hoping that would happen by. I knew when I joined Boldstart that within a year I wanted to make a decision what the next big arc would be (staying, joining a company, starting a company, etc). I didn’t need to do it by then, I just wanted to have clarity for myself and for the team. The decision solidified in the 6-9 month timeframe, well before my self-imposed deadline.
A few other techniques I use to help with seeing progress over time:
Full CV doc - I keep an open Google doc of the most interesting things that have happened, or the first time I achieved something new. In 2012 I was still adding essays I wrote, by name! It can also be things I try out as I'm exploring (I took a podcasting class last year, but haven't started one yet).
Self imposed "chapters" and "experiments" - Part of why I like moving and changing roles is that it's an easy way to brick out the different points in my life. It's roughly: Seattle/Microsoft, NYC/Kickstarter, Boston/HBS1, Blade/Lola, Dark, Michigan/HBS2, Boldstart. Each of those arcs also have a main "experiment" that was part of the time that usually shows up in a later chapter. For instance, Awesome Foundation was a group I worked with in Seattle that directly led to wanting to work at Kickstarter. Angel investing started while I was at Lola and (eventually) led to my current work. I use the work ones (no surprise there), but I can also do something similar with personal milestones - meeting Tom, moving in together, being engaged, being married, buying our house, etc. You get to choose what you anchor around.
Relationship Retreats - Every quarter, Tom and I go away for a weekend and spend 1-2 hours on reflection. We go through a few categories - health, hobbies, career, family, intimacy, finances, domestic affairs (household stuff), friends, and rest and relaxation and each individually rate how we're feeling 1-10, and what contributes to that. Then we use the time to discuss and think about what we might like to adjust to both feel our best. In career, if someone were to repeatedly assess work as a 5-6 without much movement, that'd be a sign that something is wrong (or likewise, an isolated rating of a 1 would be a huge issue). You could definitely adjust this framework to do with a friend or yourself, but I really like it in the relationship setting because we can get into so many different categories.
I hope these six things are helpful to figuring out how you can think about your work and what might get you to the roles that are the best fit:
Purpose vs. job
Defaulting to saying yes or no
Maximizing upside vs. minimizing downside
Core needs
What you’ll put up with that others won’t
Timelines and tools for self assessment
Do you have other things that have worked well for you? I’d always love to hear about them. Would more on any of these tools be helpful? Let me know.