Assess if it’s time to quit (this will shape how you approach the next steps).
If it’s time to quit, or you think it might be, figure out your constraints versus need.
Do you need to make your current role manageable to give yourself time to look for something else?
If you’re a maybe on quitting, think about what’s pushing you to that point, and what you could try to improve things.
If you’re a no, great! Less overhead for you. Move to step 2.
Look at what options you want to be available to you.
Check yourself on whether it’s a job or a title – what do you really want to be doing in your 40+ hours a week you spend at work?
Assess where you are relative to them.
For those where you’re on track, great – you’re done here.
For those where that is not the case, take them to step 3.
Define your current moment.
What is your current moment?
What do you need right now?
Given those things, what constraints do you have here?
Discuss the constraints with someone you trust – do they have to be true?
Clarify the deal you made under capitalism.
Think about what your employer is renting.
Are you building market value?
Are you undermining market value?
Think about what your employer is buying.
Is there anywhere where they are taking more than they’re paying for?
Are there any boundaries to redefine?
What kind of deal do you want?
What supports your longer term goals?
What do you need to support your life right now?
Identify some proximate objectives.
Come up with some (1-3) shorter-term goals that support what you identified as your overall career options.
Make sure you really nail the `what` and the `why` – achieving this goal is meaningful to you, and will represent meaningful progress.
Put together development plans for each of them.
Discuss and refine the plans with someone you trust.
Think about your relationship to feedback.
Identify what quadrant you’re in for some key relationships.
If it’s receptive and actionable – great, what’s working and how did you get to that point?
If it’s receptive but not actionable, or not receptive but actionable, why is that? What would help?
If it’s neither receptive nor actionable, why is this?
Is there a way to extract yourself from this situation?
Think about what you could do generally to be more coachable. Pick 1-2 suggestions from the list to work on.
Think about some difficult pieces feedback you’ve received. What can you take from them? Is there anything useful here?
“No” is okay!
Even in the worst contexts, there may be something we can learn about ourselves. And then, it’s much easier to let that feedback go.
Some feedback and feedback relationships need to go in the bin. Do you want to put anything in the bin?
Audit your network.
What relationships are good? Celebrate them.
What relationships are okay, but could be better?
Think about how things could be better.
Think about things you could do to improve those relationships.
Decide if you want to make some time to invest in those relationships.
“No” is okay!
So is “not right now”.
What relationships are missing?
Think about what those missing relationships cost you – i.e. if you have a very small professional network, maybe it makes it harder to find new opportunities.
Think about what you could do to build more of a network, what would be the easiest things you could do? What would you enjoy?
Assess the gap versus what you might do to solve it and decide whether or not you want to do it.
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.
Expect less from your job and more from your career. Your life is more than your career, and your career is more than your current job. Your current job should serve your life or career in some way, or it’s probably time to consider moving on. The goal is not to optimize for this moment – the current job – but your overall career. Sometimes jobs you don’t enjoy contribute meaningfully to your career trajectory. Sometimes jobs you enjoy are not developing your skills. Being clear about the distinction makes trade-offs explicit and decisions clearer.
Three concepts within this:
Plan for Opportunity
The Work > The Title
Define the Moment
Plan for Opportunity
Some people have a five year plan. I have optionality.
Personally I’ve never been able to connect with the idea of being able to plan your life. This is even more true in a relatively new, highly evolving industry. Who is to say the things I’ll be working on ten years from now are even viable today? If I plan, I am necessarily limiting myself to what I can see today, leaving out all the things that I am not aware of yet.
The way I think about things is less “what do I want to do?” and more “what opportunities do I want to be available to me?”. The more options something opens up, the more excited I am about it. Decisions that cut off options should be taken carefully. For instance, investing in taking coaching training has deepened or increased options available to me. Really committing to the management track has got me to a place where it would be very hard (although not impossible) to go back to being an IC.
Maybe you have a five year plan, and that’s great if it works for you. If you reframe it in terms of making those options available to you, would you be making different decisions?
If you don’t have a five year plan, what options would you like to be available to you down the line? What could you do to make those options more available to you?
The Work > The title
A job title is a few words. The work is 40+ hours a week. It makes sense to prioritize accordingly.
Job titles can be useful. Especially for people who get judged on past performance rather than potential, so – people historically marginalized in tech. I get much more interesting recruiter messages now I have a “proper” job title, versus when my job title was emoji. I also get a lot more sales emails, so I remain unclear on whether it’s a net win.
But, job titles are not comparible, are often meaningless, and usually far less impactful on your actual life (and career) than the actual work you have to do. Over-prioritizing factors relative to their impact is a fast track to making decisions that don’t best serve your overall well-being.
A job title is not a goal. Do you want to “be a staff engineer” or do you want technical leadership on complex, interesting projects. Do you want to “be a 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.
Also consider how some job titles can reduce your optionality. Once you take a manager title, it becomes harder to go back to being an IC. Once you have a VP title, it becomes harder to find another job – even if just because there are fewer of such roles available. Both of these things are fine if that’s what you want, but that’s a decision to make mindfully.
Define the Moment
This job is just a moment in your career.
Because people tend to define their career through the lens of their current role, they attach too much importance to what is currently going on, and miss its place in the bigger picture. But whatever is going on right now is just a moment in the broader arc. Your career is not defined by this any more than a month long adventure is defined by one day within it. Yes, occasionally, in extreme circumstances. But very rarely.
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 things as moments can help to give perspective and make things more endurable. Maybe your boss is abusive, but you choose to finish the project/organize your financials 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. Maybe you take on a challenge, push yourself, because you know it doesn’t need to be forever and this opportunity is worth it. Maybe your ambition did not die of COVID, maybe you just needed a moment of calm to survive living through a global pandemic.
If something feels untenable, how do you step back from it and make it a moment? What needs to change? And what resources are available to you to make that change?
The topic that got the most attention in my previous post about being the DRI of your career is the concept of rent versus buy when it comes to managing your career.
Distinguish what your employer rents versus what they buy. I find this particularly relevant when it comes to things like “personal brand”. My employer buys my time, they rent my personal brand. To that end, I’m conscious that whilst it’s part of the value I bring, I don’t want it devalued because ultimately it’s my asset for the long term. This concept also applies to expertise. My expertise is rented, and so I maintain my understanding of what it’s worth, and what is current on the open market. If your job does not match the market in a way that will make it hard for you to find another one, I hope your employer is paying a lot of rent – because they are destroying the market value. At times that might be worthwhile, but often it is not, and people realize that too late.
Here, I’ll expand a little more on how I think about that, but I’d also love your input on how you think about it and what examples you would place in each. Leave a comment, ping me on Twitter, or drop me a note.
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 is not destroying the value long term.
Expertise
Expertise is a key example here. Your expertise is yours. It’s what will help you get your next job, negotiate your salary (oh hai “market value”). Because “professional development” is a core retention strategy in tech, too many people are complacent and outsource this responsibility to their current employer, instead of being strategic in how they consider their own development. This is why there’s discussion about “staying current ” as a developer. We used to hear the phrase “there are a lot of unemployed COBOL programmers”, and now it’s more like, there are a few COBOL programmers, they make a lot of money, largely from banks or the government.
This piece is often where the side project dialog goes off the rails. Should you need to do side projects to get a job? Are open source contributions a requirement? I am a hell no on both 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.
I think 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, 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 that I see people making in this realm is the resume that shows “X years of experience” (where X>=6) but when you dig in you see the same 1-2 years of experience again and again. These people top out, stop getting recruiter pings and they don’t know why – but 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 an individual we all have a “brand” or a “profile”. At a minimum, it’s what’s on your resume, and how you build the narrative of your career. Some companies or roles are detrimental to that. If you work at a company that is materially contributing to (and profiting from) the collapse of society, that may reflect on you.
A common mistake I see is where people have a job title or custom role that does not match the market. Companies sometimes try to pay their “rent” in inflated job titles – I’m extremely skeptical about the value these have on the open market. For a good recruiter or hiring manager, a “VP” or a “Director” job title without 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 – hybrid roles where people do A and B are particularly susceptible for not meeting the criteria of either A or B 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. “And roles” where people do two+ jobs, poorly, do not set people up for success in their broader career.
But for those of us who have a bigger profile, some recognition in the community, the concept of brand goes beyond the resume. In a leadership role or DevRel, but to some extent elsewhere, your profile and ability to attract talent is 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 lately 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 point on brand doesn’t apply to everyone, but where it does it’s worth considering carefully. My main point here is: boundaries. Think about how you want to use your profile, what options you want to be available to you, what boundaries you want to set around it. Make sure that you’re balancing between the rent and ongoing market value.
Attention / Context
Attention is also rented. What do I mean by that? Often you work in a particular domain, and you pick up things about it. Maybe you work in fintech and you acquire a bunch of knowledge about financial regulation. Maybe you work on web standards, and acquire a bunch of knowledge about governance. Maybe you work in Open Source and acquire a bunch of knowledge about licenses. Your attention is directed by your domain.
When you leave, you take with you that context and what you learned, and that can help you elsewhere. Personally, I’ve been working in Open Source and building remote teams for a long time – those things have had my attention, now I know a bunch of stuff about them, and that is one less thing anyone has to explain to me when I switch jobs. In another part of my life, I did a bunch of work on presentation software and picked up various things about file formats and rendering. At times, I use these bits of information. It’s like a shorthand; I can more quickly evaluate a resume, or the likely complexity of a project, because I have that domain knowledge.
The win of attention is a little additional curiosity can result in disproportionate amounts of learning given current context. Later, you have these bits of useful information that you can use to accelerate things. Being conscious of how you allocate that can make a difference and make more opportunities available – whether you go deep, or pick up complementary / adjacent contexts. The mistake of attention is when people think they know a domain, but really they know a company. I remember the interview where someone told me they were a “$domain guy” when their understanding seemed very limited to questionable business practices of one particular company which… okay yes, did have a product in that domain.
Buy
If some things are rented, what is bought?
Time
Time is the obvious one, typically part of the working agreement, officially around 40 hours per week. Some jobs are more than that for whatever reason, and should pay more as a result.
The time aspect is interesting, because research shows that in senior roles, they are more likely to be held by men, whose wives are less likely to work. Women in these roles have fewer children, and are more likely to be single (source: HBR, see also: “7 in 10 men who have enough income to put their households in the top 1% of earners have stay-at-home spouses” Qz, “Why promoted women are more likely to divorce” BBC).
What I take from this, is that the time commitment of certain roles is such that it’s extremely challenging for someone to have such a role and be a parent. Those roles are compensated highly because it’s essentially compensating for the time of two people, where one is the “worker” and the other is the person who makes that level of work possible. The US presidency is perhaps the biggest such example, and one of the interesting things about Dr Jill Biden continuing to work at her usual job as a Professor, is that the position of “FLOTUS” (the unpaid second position that comes with POTUS) has to be filled at least somewhat by people who are actually paid… themselves… to do the work.
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, overwork, and burn out (for more on this topic, see: Figuring out Remote Work is Figuring out Work).
Energy
I include energy as 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). My theory is that when people think about how much they work, they count the energy that they spent. When they track the time, it’s more concrete. So a long dinner with friends is definitely not counted as “work time”, but if you’ve had a shitty week and spend half of it emoting… it counts energetically.
Dysfunctional environments are an energy drain way beyond the time commitment, and typically way beyond what you are actually compensated for. Thinking about it this way is an encouragement to set boundaries, or – if they aren’t respected – draw lines (like turning the phone off, or ultimately look for another job).
Adherence
Adherence is the agreements we make as part of any employment contract. Some jobs don’t allow people to do any programming/writing/speaking externally, and this can be a lot to give up. Maybe you have to live in a certain place, work out of an office, etc. In distributed contexts, travel used to be one aspect of adherence. When hiring at my last job, we would be super clear: 49 weeks of the year, you are wherever you like. 3 weeks of the year, you need to make travel work. It wasn’t for everyone, but I think that is normal and expected; not everything is for everyone.
If your employer is buying adherence, then it needs to be reasonable. Perhaps no amount of money would make you go back to an office – totally get it, but if your employer thinks they have paid for that, you are going to have to figure a way out of that disagreement that may well involve finding a new place to work. Personally, I can’t imagine selling my ability to write and code for fun ever again, but earlier in my career I made that trade-off for a while, and paid for it later.
Trade offs
Thinking about career decisions this way, you can consider different tradeoffs and options that work best for you at any given time. As an employee, it’s typical to allocate more time, more energy, and in return typically receive higher levels of investment in expertise – this helps people grow more, and ultimately earn more over time. The benefit of different working relationships, like contracting, is often to set stricter boundaries around time and energy, which can free people up for other things (or just maximize short term income). I can’t emphasize enough that all choices are valid and that people operate from wildly different constraints, many of which perpetuate systematic inequity. My question is: are you making those choices mindfully? And do they work for the life and career you want?
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