Chapter 1. Career Decisions and Optimizations

Career decisions often feel fraught and scary. Do we say yes to the big project? The new job? What are the implications? What if we fail or leave and regret it?

If we don’t have exciting new opportunities to hand, we can often second-guess ourselves. If we enjoy our job and feel comfortable doing it…are we not pushing ourselves enough? Have we stopped learning? Are we…lacking ambition? Should we interview somewhere else just to see what’s out there? Start a(nother) new side project? Switch to another team?

The risk of the career decision is that we get it wrong. But the more insidious risk is that we make a nondecision decision; because we are afraid to be wrong, we implicitly decide to keep things as they are, even when that is not working for us.

Contributing significantly to the inner turmoil is how loudly the world tells us what we should want. Years ago, Sheryl Sandberg exhorted women to lean in, and I swear that message is still echoing within me. Every week there are new think pieces warning about “quiet quitting” or why going to the office is critical for getting ahead, and viral social media posts of career and/or productivity advice abound. The cacophony of voices telling us that we are somehow not enough and probably never will be is exhausting.

You will not find any of that here; I don’t believe in offering advice1 on almost anything.2 How could I—or anyone—possibly know what is right for your career? Only you can really understand your constraints and appetite for risk and change, what you do—and don’t—enjoy doing, and how your career supports what you want from your life.

What you will find is a framework you can use to structure your thinking and make conscious, deliberate decisions about what (and why) you want now and how that fits in with what you want later.

Expecting More from Your Career and Less from Your Job

The first point in the mentality of being the DRI of your career is expecting more from your career and less from your job. Your current work situation—good, bad, or fine—is just a moment in your career. The goal isn’t to optimize for this moment—the current job—but for your overall career. Your life is more than your career, and your career is more than your current job.

We’ll break this into three concepts:

  • Planning for opportunity

  • The work > the title

  • Defining the moment

Planning for Opportunity

Some people have a five-year plan. I have optionality.

I’ve never been able to connect with the idea of being able to plan my life. This is even truer in a relatively new, highly evolving industry. Who’s to say that the things I’ll be working on five years from now are even viable today? If I plan, I’m necessarily limiting myself to what I can see today, leaving out all the things I’m not yet aware of.

I try to think about things less as “What do I want to do?” and more in terms of optionality, by asking the question “What opportunities do I want to be available to me?” The more options something opens up, the more excited I am about it. For instance, investing the time to take coaching training increased options available to me.

However, decisions that cut off options should be made carefully: by the very nature of removing options, you remove trajectories of growth. The more I commit to the management track, the harder it gets to go back to being an individual contributor. When I first shifted into management, I didn’t really think through the consequences, but when I shifted from my first to second management role, I thought deeply about whether I wanted to continue on that track, what the alternatives would be, and what it would take to get back on the IC track (a calculation I periodically rerun).

Some decisions cut options off indefinitely, but some just cut options off for a time. When I decided to write a book, I knew I would need stability to carve out time for that and wouldn’t be looking to shift jobs or to take on too much more responsibility while the project was underway.3 The short-term trade-off was worth it to achieve a long-term goal that I hoped would provide more optionality later.

The Work > The Title

A job title is a few words. The work is 40 or more hours a week. It makes sense to prioritize accordingly.

A job title isn’t a goal. Job titles can be useful, especially for people who get judged on past performance rather than potential—in particular, this occurs with people who are historically marginalized. Once I got a “proper” job title (Director, Native Apps), I started getting much more interesting recruiting messages compared to when my job title was defined in emojis (📱👑), even if both roles were functionally very similar. I also got a lot more sales emails, so it remains unclear as to whether it was a net win.

The big problem with job titles is that they aren’t comparable: they exist in the context of an industry and an organization’s structure, values, and modes of operation. As a result, they are often meaningless and are usually far less impactful on your life (and career) than the actual work you do. Over-prioritizing factors relative to their impact is a fast track to making decisions that don’t best serve your overall well-being.

Do you want to be a “staff engineer,” or do you want technical leadership on complex, interesting projects? Do you want to be a “Vice President of Engineering (VPE),” or do you want a job that combines organizational and technical leadership of a large organization? Using job titles can seem like a useful shorthand, but it’s easy to default to chasing status over what will actually make you happy. Be specific about what you want and why you want it. Think critically about the work you actually enjoy and how you add value.

Finally, consider how some job titles can reduce your optionality and make finding your next role more difficult. Even considering how titles can scale across different-sized organizations, once you take a manager title, it becomes harder (although not impossible!) to go back to being an IC. Once you have a VP title, it can become harder to find another job at this level—even if it’s just because there are fewer of these roles available. While recruiters often find people based on keyword searches including job title, it’s common knowledge that job titles are often meaningless. If your responsibilities and scope don’t match your title, this will usually come up very quickly when you are interviewing, and that may count against you.

Defining the Moment

This job is just a moment in your career.

Because people tend to define their careers through the lens of their current roles, they attach too much importance to what’s currently going on and miss its place in the bigger picture. Whatever is going on right now is just a moment in the broader arc (Figure 1-1). Your career is not defined by this any more than a monthlong adventure is defined by one day within it. Yes, occasionally, in extreme circumstances. But it’s very rare.

The bigger picture is the most important thing. Even if you see a small dip in trajectory, the overall trend is moving up.
Figure 1-1. The bigger picture is the most important thing; even if you see a small dip in trajectory, the overall trend is moving up

Deciding what this moment is helps you decide what to do with it:

…a moment of opportunity

What potential does this create? What optionality does it facilitate?

…a moment of challenge

This is the power of the stretch assignment—meet the challenge, see what opens up as a result.

…a moment of trauma

The most dangerous moment—is this moment creating something you will carry with you and need to untangle later? Tread carefully.

…a moment of calm

Sometimes we need our jobs to just be fine—not too stressful, not too challenging—to create space for other things in our lives.

Looking at time spent in roles or organizations as moments can help give perspective and make things more endurable. Maybe your work situation is horrible, but you choose to finish the project/organize your finances before you move onto something new—despite how miserable that sounds, there is huge power in choosing to endure something for your own reasons rather than being a victim of circumstance.4 Maybe you take on a challenge and push yourself because you know it doesn’t need to be forever and this opportunity is worth it. Maybe your ambition did not die because of COVID-19; instead, you just needed a moment of calm to survive living through a global pandemic.

It’s critical that we step back to consider what we genuinely want—not what we think we should want or what we think we might want—and how to create and validate those options.

The trap of the “should” want is why the job-title trap can be so risky: we push ourselves to chase a title without taking time to think about the work we truly enjoy. The trap of the moment is that it destroys our boundaries and puts us in a place of “when our job sucks, our life sucks.” A bad relationship with our work is rarely contained to the time we spend doing it—instead, it spills over into our evenings and our weekends, through our conversations, and into the energy it drains from us.

Even if you have excellent boundaries, 40 or more hours a week is a lot of time to be unhappy: figuring out the optionality you want to be available to your future self helps you define the current direction, understanding the work you really enjoy gives you clarity about what you’re moving toward (independent of the title associated with it), and defining the moment gives a sense of purpose. Understanding these three things can help you redefine how your current role fits into the overall arc of your career—and how that interacts with the kind of life you want.

Distinguishing What Your Employer Rents Versus What They Buy

I used to work at a company that—even at more than 1,000 people—rejected a lot of traditional wisdom about how tech companies should be run. There was no product management, no CTO, no VPE, no promotion or leveling system. Some people might have run from such a situation, but I did not. I initially joined to run the mobile team (at the time I joined, a disconnected nonteam of around 20 people) because it was a great opportunity for me and a significant step up from what I was doing previously,5 and it did not require me to relocate to the United States. I figured I would have a very difficult 18 months riding the learning curve and getting things sorted out, but after that I would have a job I really loved.

Well, half of that ended up being true. After the very difficult 18 months, we became a high-performing team of 40–50 people, and others in the organization were impressed by what we had accomplished. However, there was no pay raise or promotion (because those things didn’t really exist). Instead, I was given another team to “fix”—which, OK, I took because I saw how running a nonmobile team would provide more optionality in my career, and because I really value being a team player and doing the right thing for the organization.

Fast-forward another 18 months, and it was apparent to me that my job had evolved into a terrible approximation of a VPE job but without the title (thankfully, I didn’t even want the title; see “optionality”) or compensation (this bit would have been nice). I was tasked with scaling hiring, managing recruiters (which I hated), and trying to provide support to leads in a system that structurally undermined them. I felt like everyone else’s problems ended up on my desk. Team not delivering? Fingers were pointed at us for not having staffed it. Team needed to be dismantled? Somehow my job. Teams not onboarding? We’re trying here!

Meanwhile, I had no power to make any of the structural changes I’d been able to make when I was in more of an engineering director role: setting standards, supporting people to meet them, and leveling them up to support the needs of a growing team. Being disconnected from shipping product made it harder to demonstrate the kind of outcomes (improved effectiveness and delivery) that made the people-centric work feel impactful.

While there were clearly many things I didn’t enjoy about this situation, the thing that really pushed me to leave is this: it was clear to me that a situation where I had responsibility but not power, where I owned process but not outcomes, was a situation where I was making myself less employable on the open market. It was also clear that this situation was a product of organizational values, which are not completely intractable but are often the slowest things to change in an organization. Those values were not going to change on a time frame that I could live with. It’s one thing to suffer for growth (during the first 18 months of the role), but it’s another to suffer while knowing that every month I spent there, I was making it harder for myself to move onto something better elsewhere.

My employer was taking the thing it rented—my expertise—and eroding the market value of it, all while paying significantly below market value for the thing it bought—my time.

Reframing my thinking this way brought so much clarity to this situation, and when I first shared this framework on my blog, this point was the thing that resonated the most with people. Again, we’re looking at this from a long-term point of view, and what seems like a reasonable bargain in the day-to-day isn’t necessarily a good long-term decision—much like eating 20 avocados a day makes it hard to buy property (OK, the avocado thing never happens except in the New York Times, but the job thing totally does).

The point of this is it’s an opportunity to step back and consider the components of value that you trade with your employer for money (and, where applicable, equity) and consider if that trade is working for you.

Rent

When you “rent” something out, you retain ownership of it—the renter just gets the use of it. As the long-term owner of the asset, it’s on you to be conscious of the value and make sure the renter isn’t destroying the long-term value.

Expertise

Expertise is a key example of what your employer rents. Your expertise is yours. It’s what will help you get your next job and negotiate your salary (oh hai “market value”).

This is why there’s discussion about “staying current” as a developer—and why managers worry that if they get away from the code, it will be hard to go back to being an IC. Our expertise is only valuable if we can do the work that is needed today, so we have to keep developing our skills with a mind to the future. The more Swift replaced Objective-C, the more important it was for iOS (and MacOS) developers that Swift was part of their day-to-day, because the ability to write Objective-C was clearly becoming less valuable over time. At university they used to warn us, “There are a lot of unemployed COBOL programmers.”6

This idea is often where the side-project dialogue goes off the rails. Should you need to do side projects to get a job? Are open source contributions a requirement? I personally say no to both of these points. However, being strategic about where you invest resources (time and money) and/or developing a habit of deliberate practice can help you develop your expertise and command a higher rent on the market. The extent of that investment is up to you (we’ll talk more about this in Chapter 3).

Developers, if they are lucky, can largely get away without thinking too critically about this because professional development is a core retention strategy of most “good” tech companies. But at smaller companies, at levels above senior developer, or in management, training is often limited and deficient, and if the individual doesn’t take control over their own growth, they will hit a ceiling.

As a hiring manager, the biggest mistake I see people making in this realm is having a resume that shows “eight years of experience,” but when you dig into the roles, you see the same couple of years of experience again and again. Some people choose the same types of roles deliberately; they specialize their roles in a way that works for them. However, people who don’t choose deliberately, or who fall into this trap early, top out and stop getting recruiter pings, and they don’t know why—it’s because they didn’t consider how to grow their expertise as they switched (or didn’t switch) jobs.

Brand

There used to be a lot of discussion about “personal branding,” and frankly, it was nauseating. But as individuals, we all have a “brand” or a “profile.” At a minimum, this is what’s on your resume and how you build the narrative of your career. Some companies on your resume will help you get interviews long past when you worked for them. However, some companies or roles are detrimental to that. If you work at a company that’s materially contributing to (and profiting from) the collapse of society, that may reflect on you.

Another mistake I see often is where people have a job title or custom role that doesn’t match the market—and they don’t realize it. Companies sometimes try to pay their “rent” in inflated job titles; I’m extremely skeptical about the value these have on the open market, which is another reason why it’s important to evaluate the work you’ll actually be doing more carefully than the job title when considering new roles. For a good recruiter or hiring manager, seeing a “VP” or a “Director” job title for a candidate who doesn’t possess an expected scope of responsibility opens more questions than it answers. It’s worth mapping your responsibilities to the expectations of the market periodically and checking that you’re still generally employable.7 Hybrid roles where people perform two different job functions (sometimes called “and roles”) are particularly susceptible to not meeting the criteria of either role externally. An “and role” can be a plus when you do one thing particularly well but have additional skills—for example, an engineering manager who does some product work or a designer who also does some CSS. However, “and roles” where people do two or more jobs poorly don’t set them up for success in their broader career.

But for those of us who have a bigger profile or some recognition in the community, the concept of brand goes beyond the resume. In a leadership role or developer relations—but to some extent elsewhere—your profile and ability to attract talent are part of your value to a company. It’s important to remember that you retain ownership of your profile and that it’s for the long term. You don’t want to be seen as a shill for a company that later turns out to be problematic.

I saw a tweet (Figure 1-2) that made me think about this; the company thought they were buying this person’s profile. But she was clear it wasn’t even available for rent.

This subpoint on brand doesn’t apply to everyone, but where it does, it’s worth considering carefully. The main thing here is boundaries. Think about how you want to use your profile, what options you want to be available to you, and what boundaries you want to set. Make sure you’re balancing between the rent and the ongoing market value.

Tweet from @tarah dated September 15, 2021.
Figure 1-2. Tweet from @tarah dated September 15, 2021

Buy

When you sell something, you transfer ownership—it’s not yours any longer; it belongs to the buyer. When you can’t get something back, you need to think critically before you part with it.

There are three major things that your employer buys when you work for them: time, energy, and adherence. We’ll talk more about managing time and energy in Section 2, “Self-Management”, but here we’ll focus on the exchange being made.

Time

Of all the things your employer buys, time is the most obvious. Whatever bargain we’ve made when it comes to time—an incredibly demanding job or a flexible job—we sell our employer some amount of time. Upholding boundaries around what is work time and what is not affects both our effectiveness and the overall quality of our lives. Most full-time jobs are around 40 hours per week. Some jobs take up more time than that for whatever reason, and they should pay more as a result.

The time aspect almost certainly contributes to systemic inequity; for instance, research shows that senior roles are more likely to be held by men whose wives are less likely to work. Women in these roles have fewer children, and they’re more likely to be single.8

More senior roles tend to be heavily scheduled and meeting driven. However, at the IC level, people still have to balance their life around their work or, now that we operate more flexibly and more from home, balance their work around their life. Based on my experience of working in a distributed context for years, the biggest mistake people make with time is that they don’t manage it well. Some people cannot cope with the flexibility; they fail to give themselves the structure they need to be effective. The other failure mode is the opposite: people struggle to disconnect from work, then overwork and burn out.

Energy

Energy is distinct from time, as I think it’s what explains the continual gap between the hours that people work and the hours that people think they work (much more).9 My theory is that when people think about how much they work, they count the energy they spend. When they track the time, it’s more concrete. So while a long dinner with friends is definitely not counted as “work time,” if you’ve had a dreadful week and spend half of that dinner venting about how much you hate your job, it counts as energy spent on work, and you think you “worked” more than you did.

It’s easy to keep thinking about work even when you’ve stepped away from the computer, especially the worst parts of your day. It’s worth asking yourself the question of whether thinking or talking about work is actually necessary or useful to you and how you can let it go, enjoy your evening or weekend, and pick it up again the next working day. More extreme, dysfunctional environments are an energy drain way beyond the time commitment, and typically way beyond what you’re actually compensated for. Thinking about it this way is an encouragement to set boundaries or—if they aren’t respected—make changes (like turning the phone off or ultimately looking for another job).

Adherence

Adherence is the agreement we make as part of any employment contract. Some jobs don’t allow people to do any programming/writing/external speaking, and for some people, this can be a lot to give up. Or maybe you have to live in a certain place, work out of an office, and so on. In distributed contexts, travel used to be one aspect of adherence. When hiring at Automattic, we were super clear: for 49 weeks of the year, you could be wherever you like, but for three weeks of the year, you would be expected to travel. It wasn’t for everyone, but I think that’s normal and expected; not everything is for everyone.

If your employer is buying adherence, then it needs to be reasonable for you to adhere to it. Perhaps no amount of money would make you go back to an office—I totally get it—but if your employer thinks they have paid for that, you’ll have to figure a way out of that conflict that may well involve finding a new place to work. Personally, I can’t imagine agreeing not to write and code for fun ever again, but earlier in my career, I made that trade-off for a while.

Trade-offs

When you think about career decisions in terms of renting and buying, you can consider different trade-offs and options that work best for you at any given time. As an employee, it’s typical to allocate more time and more energy and, in return, to receive higher levels of investment in expertise than as a freelancer; this helps people grow more and ultimately earn more over time, even if their hourly rate is lower. Sometimes people want to enforce stricter boundaries around time and energy, which can free them up for other things.

I can’t emphasize enough that all choices are valid. Most of us make different choices at different stages in our career, and people operate from wildly different constraints.10 My question is: are you making these choices mindfully? And do they work for the life and career you want?

1 And yet I still decided to write a book.

2 The three topics I will confidently offer advice on are: (1) don’t fracture your shoulder; (2) when your job gets harder, the best thing you can do is make a friend; and (3) skin care.

3 Deep-in-finishing-the-book Cate laughs (hysterically) at the past Cate who thought she might pull this one off.

4 All credit to my therapist for this revelation!

5 Running a six-person team at a failing startup while being a questionably legal migrant in Colombia.

6 Now it’s more like there are a few COBOL programmers, and they make a lot of money, largely from banks or the government. So I guess sometimes it works out!

7 My suggestion is to take some recruiter calls and do some interviews. Treat it like an information-gathering session and just see what you learn. You can also go to some industry events, seek out some blogs or books, and try to understand the work of other people who have similar job titles to determine where your gaps are.

8 See Boris Groysberg and Robin Abrahams, “Manage Your Work, Manage Your Life”, Harvard Business Review (March 2014); Lila MacLellan, “70% of Top Male Earners in the US Have a Spouse Who Stays Home”, Quartz, April 30, 2019; and Maddy Savage, “Why Promoted Women Are More Likely to Divorce”, BBC, January 22, 2020.

9 Author Laura Vanderkam—my favorite writer on the topic of time—strongly recommends time tracking for this.

10 It’s worth noting that systemic inequity drives many constraints—for instance, caregivers have more constraints around time.

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