How I manage my career like I manage my products

It’s all about thinking iteratively, prioritizing learning and realizing that no single decision will permanently dictate the rest of your life...I promise.

Are you struggling to decide if you should start looking for a new job or not? Are you in the middle of weighing a few options for what job you want to take next? Do you feel like you are kinda wandering through your career unsure if you’re really in control at all?

We’ve all been there. Because careers are personal. Trying to live up to “figuring out what we want to do with our LIVES” is stressful. Having to deal with rejection, other people’s judgement, event our OWN judgement, is emotional.

What’s helped me manage all of the emotional baggage related to my “career” is to put on my product manager hat. So instead of feeling overwhelmed and unsure, I approach my career decisions with a product mindset and therefore the same humble confidence I would in making any product decision.

What does that look like? There are three main elements…

1. Set your overall career vision. When you’re working on a product you need some kind of over-arching vision for what you are trying to do. This might change over time, you can’t be 100% sure that this is the overall direction you should go in. But you do need to set some high-level theme that will set boundaries for all of the lower-level iteration you are going to do. For example, a product I once worked on believed that connectedness in the workplace is a driver for employee productivity and retention. And we believed that we could build a product that improved connectedness across employees and that companies will be willing to pay for that. Now, at the time I joined, we didn’t yet know for sure that that was true. But what that framing gave us were boundaries to work within so that everything we were designing and testing would help us either confirm our deny those beliefs. Otherwise we could have been trying a million different things that weren’t connected at all which could have resulted in us being extremely lucky and finding something that took off, but more than likely it would have resulted in very little progress. So, I do something similar for my career. Here’s an example of my vision that I brain-dumped into a google doc 3 years ago….Based on what I know right now (and remember, this CAN and WILL change…so don’t obsess over this, set the best vision you can as of today and move on) I have a few hypotheses for what I think I want to achieve in ~5 years or so. I think I either will want to be a head of product at mid-stage startup with a product I think helps people in some way, start my own non-high-growth company with a mission that’s important to me, or have a few years of individual freelance work that allows me to have a flexible travel life. Now, I could have learned something in my next job that TOTALLY changed all of those hypotheses and I caused me to head in a totally different direction. And if that happened, that would have been cool. But what putting this stake in the ground a few years back allowed me to do was to identify, based on my guesses at the time, what was most important for me to learn to either prove or disprove my career hypotheses as quickly as possible AND what skills I needed to prioritize building up to ultimately get me to one of those results. Which brings me to step 2…

2. Define your short-term career priorities. Now that you have a helpful frame to work within, you can use that overall vision to define the immediate priorities that are most important right now. These priorities are how you are going to assess your next potential steps and how you will make informed decisions. Continuing my product example from above, knowing that our overall vision was to build a product that improved employee connectedness that actually worked (meaning that it drove long-term employee retention & performance), that employees used and companies paid, for I had 3 product priorities that were most important for us to figure out. First — what types of companies, if any, had this problem? Second — what capabilities did our product need to have to actually solve this problem? And third — how would we actually get people at our target companies to start using our product enough for the product to actually do what we claimed it did. And literally everything we planned on doing had to be in service of answering those questions. If something was not going to help us learn something new around those 3 priorities, then it was not a priority. So when someone brought an idea of something we could do, it wasn’t stressful for me to decide if it should be a priority or not. I didn’t get attached to the idea and try to decide if I liked it more than others. I simply asked myself, “how much will this help me achieve our top three priorities?” And I used that answer to rank it against the millions of other things we could do. So, again, I use the same process for my career. Based on my overall career vision from a few years back, the first thing that I thought was most important that would help all three potential futures was continuing to deepen my product management expertise as much and as fast as possible. That was my number one priority. I decided my second priority was actually becoming stronger at a few product-adjacent skill sets as well, things like marketing, sales, branding, etc. To me, this would both help me learn if I did want to go down the founder or freelance path where I would actually need to do a lot of this type of work myself AND would help me be a better future Head of Product because these are functions that I would be partnering with. So it was helpful for all my potential visions as well. Helpful to validate my interest (or lack of interest) in two of them, and to increase the chances of one. My third short-term career priority was learning how to grow product usage from nothing to something. All my previous product experience had been around learning how to take an existing product reaching millions of monthly users and grow it to more millions. Great experience, but I had yet to learn myself how you get it to those first million users! I felt like that would not only be a good competitive advantage for me to have for all of my long-term vision options but also it just got me EXCITED. Even when I write it out now in my head I’m STILL like, “hell yea, I’m gonna get those first million.” So I knew that was important for me in whatever I did next. Even if doing that led me to learning that I didn’t actually like it, then I would know! Note, these priorities are outcome-focused and purposefully INDEPENDENT of the solution. By this I mean, a priority of mine was not “get a new job”. And that’s because getting a new job is not the outcome. It’s a means of achieving an outcome. I wanted to get better at certain PM skills…I still had to decide, was staying at my current job the best way for me to do that? OR would getting a job at a specific type of company be a better way? OR maybe starting to pick up some side hustles? The point is, we so often get tied to a narrative in our head…does something like, “omg I’m SO unhappy at work, I have no career trajectory here and I NEED to get out now.” Sound familiar?! The problem here is that you’re combining your short-term priorities (being happy at work and having growth potential) with a one of many potential solutions (getting a new job). Yes, getting a new job could be one way to achieve your priorities. But another could be switching to a different team at your current company with a boss you jive better with. Or having a candid conversation with your boss. Or taking on side-projects at work to try out different functions and see if that might be what’s causing your unhappiness and it’s not the company at all. Jumping straight to the solution not only makes you blind to the millions of other options you have but most tragically it increases the chance that you’re not going to achieve your priorities even once you achieve what you have laid out. Because you jumped to a solution to solve your problems that you haven’t actually validated in any way that it WILL solve your priorities. And this is why so many people get a new job and then 6 months later, once the new-ness wares off, are unhappy yet again. So please, take the time to tangibly identify these priorities…make SURE they do not include a solution within them and THEN freely list out all your potential options. From there you can look at your list and it is WAY more freeing and exciting to see how many options you get to pick from rather than stressful thinking your only solution is one thing. The former feels like you’re in control, the latter like you have to complete a miserable task that you didn’t even get to choose yourself. Going through the list, you can think critically about which are most likely to help you achieve your priorities (ex: getting a job at a company with a WORSE culture is 100% possible, so you cannot say this potential solution will with 100% chance solve your problems) and which are actually most likely to happen (ex: switching teams at your current company might be easier and faster than getting a new job. So in a shorter amount of time you could confirm if in fact it is a company problem or if it turns out it was just a team/boss problem). THIS is how you think with a product-mindset about your career. What is my general hypothesis/vision, what are my priorities in order to achieve that vision, and of all of my potential ways to achieve those priorities how can I validate quickly and cheaply which is likely to be the best way? And then once you do this, PLEASE remember you aren’t magically done managing your career for the rest of your life…

3. And you must continuously adjust you vision and priorities based on your career learnings. The biggest parallel I always remind myself between managing my career and managing my product is that I don’t know shit. And I hate to break it to you, but you don’t either. I know what I think I know but the whole goal is to learn more so I can gain more data and gather more insight in order to turn my hypotheses (read: guesses) into things I know (read: guesses I’ve proven to be right or wrong). 10 years ago one of my hypotheses what that I would love product management. I could have been completely wrong. But I tried it and decided I liked it enough, so that gave me more confidence in that hypothesis. I didn’t love it yet though. So my SECOND hypothesis was that maybe I could still love product, but in a different company environment and in a different product space. So instead of totally changing my job function, I tweaked other elements of my job — going to a smaller company, trying a couple different industries, trying different product cultures. Through each of these steps I confirmed certain things that I had guessed I might like while also learning other things that I was definitely wrong about. You should get in a regular rhythm of checking your overall career vision, seeing if it still rings true, and updating your career priorities based on what you have learned since you last set them. Similar to managing your product, your short-term priorities should actually change quite often as you achieve some on your list and make progress towards others. And your overall vision should definitely evolve over time as well, it should change less often.

And how do I try to do this for myself?

I personally like the rhythm of checking in every 3 months. Every 3 months I sit down with what my short-term priorities were for the last 3 months and see where I’m at and what I’ve learned. How much do I think my product skills have evolved over the last 3 months (H/M/L)? How much have I learned about product-adjacent functions? And how much have I learned about how to build a product from nothing to something?

You might do a check and see that you’re scoring high on ALL of the things that are important to you right now AND that you are feeling motivated and fulfilled by that. In that case you probably don’t need to make a major career change right then. But to keep you progressing and learning, you should probably set some new short-term priorities that will set you up for continuing on this trajectory.

You might do a check and see that you are more in the middle. In those cases I ask myself, what can I change to change it to high markings? Similar to product, I like to see what low effort changes are available to me first. Are there known opportunities within my current job that I could just start doing tomorrow? Are there potential opportunities in my current company that I could start working towards (ex: launching a new product that supports your current companies mission, putting your hat in the ring for that new management position, creating an opportunity for a new position yourself)? Maybe you try these things for another 3 months and you realize there hasn’t been much movement…maybe you’ve been at a medium “meh” for the last 3 times you’ve done this assessment. In my mind that’s as bad as being at a “low” on everything once. This is the time to starting assessing a more major change. If you still feel like your career vision rings true then you gotta start seeing what other options are out there that would get you to HIGH on your priorities. You can’t keep waiting to “see if it changes”. You gotta do something.

You also might be in a place where you score high on all your priorities but for some reason that doesn’t actually make you feel happy when you see it. Maybe you have this gut feeling that something is off even though everything is telling you it shouldn’t be off. This suggests it’s time to reconsider your overall vision. Maybe what you’ve been working towards isn’t actually your goal anymore. Maybe what you’ve really learned is that yes, you could achieve it and you’re on the right path to doing that, but you don’t actually want to achieve it anymore. This is also SUCH valuable learning and it’s an opportunity to now find your new vision. It’s not a step backward, it’s a step forward because you now know something valuable that you didn’t before, you know one more thing that isn’t for you.

As for me, it’s been kind of fun to look back at my potential visions & short-term priorities from three years ago. Through the job I was in when I wrote those, I definitely strengthened my overall product skills AND learned a lot about non-product functions because I took on a lot outside of the product team knowing that I wanted to learn those skills. I also learned a lot about taking a product from 0 to 1….but I knew there was definitely still more to learn there, so that one wasn’t completed yet. It turns out, that while I still thought that I likely wanted to eventually be head of product and/or start my own biz…due to some personal things that happened that year I decided that it was the best time to see if I was really serious about the whole freelancing-while-traveling idea. And so I spent the following year traveling through Remote Year, living in a different country every month and freelancing for the first time! And wow, I learned SO much through that. Enough to fill a full article on it’s own. And honestly I loved it. But for a lot of different reasons than what I also loved my previous job for. And NOW, after doing that for a while, because of OTHER personal things that came up, I’m back to being in one place and am now actually head of product :) still at an early stage startup, still working every day to build a different product from 0 to 1. With an updated vision for the next ~3 years of my career and a different set of short-term priorities.

Which brings me to the last point I’ll make for this article. Which is throughout all of this, please remember this: none of these decisions are permanent. Often times we stress out SO much about our career decisions because we fear making the WRONG decision. As if once we do, we will literally never be able to change it and be stuck with that wrong decision for the rest of our lives. And that is just simply not true at all. Yes, you don’t want to continually take a job that you end up leaving after a few months over and over and over again. But, I promise you’re allowed to do that a few times in your career. We all have been there. And it’s better to learn quickly your guess was wrong than to waste years of your life just to prove to yourself or others that you weren’t “wrong”. Waste of precious time. If you accept a job and hate it, you can leave. If you stay at your current job and continue to hate it, you can still leave. I’ve even accepted a promotion at a current job and then within the same week put in my notice because an opportunity that I wasn’t expecting came up and I decided that’s what I thought was best for me to do. At first my brain told me, well that’s too bad Sarah, you just accepted this promotion so you can’t leave now. But then my PM brain popped in and said, “wait, why not?”….Why not indeed.

I encourage you to keep that question in your back pocket. For when your emotional and scared brain fights against your new career-decision-making toolkit. And I encourage you to use this framework to approach your career with a lens of possibility, excitement, and problem-solving rather than one of fear, unrealistic expectations and permanence. Because in the end, it’s all made up anyway 😉