One of my stretch goals for 2019 was to start writing an advice column.  I get a lot of questions about everything under the sun: observability, databases, career advice, management problems, what the best stack is for a startup, how to hire and interview, etc.  And while I enjoy this, having a high opinion of my own opinions and all, it doesn’t scale as well as writing essays.  I do have a (rather all-consuming) day job.

So I’d like to share some of the (edited and lightly anonymized) questions I get asked and some of the answers I have given.  With permission, of course.  And so, with great appreciation to my anonymous correspondent for letting me publish this, here is one.

Hi Charity,

I’ve been in tech for 25 years.  I don’t have a degree, but I worked my way up from menial jobs to engineering, and since then I have worked on some of the biggest sites in the world.  I have been offered a management role many times, but every time I refused.  Until about two years ago, when I said “fuck it, I’m almost 40; why not try.”

I took the job with boundless enthusiasm and motivation, because the team was honestly a mess.  We were building everything on-prem, and ops was constantly bullying developers over their supposed incompetence.  I had gone to conferences, listened to podcasts, and read enough blog posts that my head was full of “DevOps/CloudNative/ServiceOriented//You-build-it-you-run-it/ServantLeaders” idealism.  I knew I couldn’t make it any worse, and thought maybe, just maybe I could even make it better.

Soon after I took the job, though, there were company-wide layoffs.   It was not done well, and morale was low and sour.  People started leaving  for happier pastures.  But I stayed.  It was an interesting challenge, and I threw my heart and soul into it.

For two years I have stayed and grinded it out: recruiting (oh that is so hard), hiring, and then starting a migration to a cloud provider, and with the help of more and more people on the new team, slowly shifted the mindset of the whole engineering group to embrace devops best practices.  Now service teams own their code in production and are on-call for them, migrate themselves to the cloud with my team supporting them and building tools for them.  It is almost unrecognizable compared to where we were when I began managing.

A beautiful story isn’t it?  I hope you’re still reading.  🙂

Now I have to say that with my schedule full of 1:1s, budgeting, hiring, firing, publishing papers of mission statements and OKRs, shaping the teams, wielding influence, I realized that I enjoyed none of the above.  I read your 17 reasons not to be a manager, and I check so many boxes.  It is a pain in the ass to constantly listen to people’s egos, talk to them and keep everybody aligned (which obviously never happens).  And of course I am being crushed between top-down on-the-spot business decisions and bottom-up frustration of poorly executed engineering work under deadlines.  I am also destroyed by the mistrust and power games I am witnessing (or involved in, sometimes). while I long for collaboration and trust.  And of course when things go well my team gets all the praise, and when things go wrong I take all the blame.  I honestly don’t know how one can survive without the energy provided by praise and a sense of achievement.

All of the above makes me miss being an IC (Individual Contributor), where I could work for 8 hours straight without talking to anyone, build stuff, say what I wanted when I wanted, switch jobs if I wasn’t happy, and basically be a little shit like the ones you mention in your article.

Now you may say it’s obvious: I should find a new IC job in a healthier company.  You even wrote about it.  Going back to IC after two years of management is actually a good move.

But when I think about doing it, I get stuck.  I don’t know if I would be able to do it again, or if I could still enjoy it.  I’ve seen too many things, I’ve tasted what it’s like to be (sometimes) in control, and I did have a big impact on the company’s direction over time.  I like that.  If I went back to being an IC, I would feel small and meaningless, like just another cog in the machine.  And of course, being 40-ish, I will compete with all those 20-something smartasses who were born with kubernetes.

Thank you for reading.  Could you give me your thoughts on this?  In any case, it was good to get it off my chest.

Cheers,

Cog?

Dear Cog?,

Holy shitballs!  What an amazing story!  That is an incredible achievement in just two years, let alone as a rookie manager.  You deserve huge props for having the vision, the courage, and the tenacity to drive such a massive change through.

Of COURSE you’re feeling bored and restless.  You didn’t set out on a glorious quest for a life of updating mission statements and OKRs, balancing budgets, tending to people’s egos and fluffing their feelings, tweaking job descriptions, endless 1x1s and meetings meetings meetings, and the rest of the corporate middle manager’s portfolio.  You wanted something much bigger.  You wanted to change the world.  And you did!

But now you’ve done it.  What’s next?

First of all, YOUR COMPANY SUCKS.  You don’t once mention your leadership — where are they in all this?  If you had a good manager, they would be encouraging you and eagerly lining up a new and bigger role to keep you challenged and engaged at work.  They are not, so they don’t deserve you.  Fuck em.  Please leave.

Another thing I am hearing from you is, you harbor no secret desire to climb the managerial ranks at this time.  You don’t love the daily rhythms of management (believe it or not, some do); you crave novelty and mastery and advancement.  It sounds like you are willing to endure being a manager, so long as that is useful or required in order to tackle bigger and harder problems.  Nothing wrong with that!  But when the music stops, it’s time to move on.  Nobody should be saddled with a manager whose heart isn’t in the work.

You’re at the two year mark.  This is a pivotal moment, because it’s the beginning of the end of the time when you can easily slip back into technical work.  It will get harder and harder over the next 2-3 years, and at some point you will no longer have the option.

Picking up another technical role is the most strategic option, the one that maximizes your future opportunities as a technical leader.  But you do not seem excited by this option; instead you feel many complex and uncomfortable things.  It feels like going backwards.  It feels like losing ground.  It feels like ceding status and power.

“Management isn’t a promotion, it’s a career change.”

But if management is not a promotion, then going back to an engineering role should not feel like a demotion!  What the fuck?!

It’s one thing to say that.  Whether it’s true or not is another question entirely, a question of policy and org dynamics.  The fact is that in most places, most of the power does go to the managers, and management IS a promotion.  Power flows naturally away from engineers and towards managers unless the org actively and vigorously pushes back on this tendency by explicitly allocating certain powers and responsibilities to other roles.

I’m betting your org doesn’t do this.  So yeah, going back to being an IC WILL be a step down in terms of your power and influence and ability to set the agenda.  That’s going to feel crappy, no question. We humans hate that.

Three points.

1. 1. 1. You cannot go back to doing exactly what you did before, for the very simple reason that you are not the same person.  You are going to be attuned to power dynamics and ways of influencing that you never were before — and remember, leadership is primarily exercised through influence, not explicit authority.Senior ICs who have been managers are supremely powerful beings, who tend to wield outsize influence.  Smart managers will lean on them extensively for everything from shadow management and mentorship to advice, strategy, etc.  (Dumb managers don’t.  So find a smart manager who isn’t threatened by your experience.)
      2. You’re a short-timer here, remember?  Your company sucks.  You’re just renewing your technical skills and pulling a paycheck while finding a company that will treat you better, that is more aligned with your values.
      3. Lastly (and most importantly), I have a question.  Why did you need to become a manager in order to drive sweeping technical change over the past two years?  WHY couldn’t you have done it as a senior IC?  Shouldn’t technical people be responsible for technical decisions, and people managers responsible for people decisions?
         Could this be your next challenge, or part of it?  Could you go back to being an engineer, equipped with your shiny new powers of influence and mystical aura of recent management experience, and use it to organize the other senior ICs to assert their rightful ownership over technical decisions?  Could you use your newfound clout with leadership and upper management to convince them that this will help them recruit and retain better talent, and is a better way to run a technical org — for everyone?

    

I believe this is a better way, but I have only ever seen these changes happen when agitated for and demanded by the senior ICs.  If the senior ICs don’t assert their leadership, managers are unlikely to give it to them.  If managers try, but senior ICs don’t inhabit their power, eventually the managers just shrug and go back to making all the decisions.  That is why ultimately this is a change that must be driven and owned — at a minimum co-owned — by the senior individual contributors.

I hope you can push back against that fear of being small and meaningless as an individual contributor.  The fact that it very often is this way, especially in strongly hierarchical organizations, does not mean that it has to be this way; and in healthy organizations it is not this way.  Command-and-control systems are not conducive to creative flourishing.  We have to fight the baggage of the authoritarian structures we inherited in order to make better ones.

Organizations are created afresh each and every day — not created for us, but by us.  Help create the organization you want to work at, where senior people are respected equally and have domains of ownership whether they manage people or technology.  If your current gig won’t value that labor, find one that will..

They exist.  And they want to hire you.

Lots of companies are DYING to hire this kind of senior IC, someone who is still hands on yet feels responsibility for the team as a whole, who knows the business side, who knows how to mentor and craft a culture and can herd cats when nec

There are companies that know how to use ICs at the strategic level, even executive level.  There are bosses who will see you not as a threat, but as a *huge asset* they can entrust with monumental work.

As a senior contributor who moves fluidly between roles, you are especially well-equipped to help shape a sociotechnical organization.  Could you make it your mission to model the kind of relationship you want to see between management and ICs, whichever side you happen to be on?  We need more people figuring out how to build organizations where management is not a promotion, just a change of career, and where going back and forth carries no baggage about promotions and demotions.  Help us.

And when you figure it out, please don’t keep it to yourself.  Expand your influence and share your findings by writing your experiences in blog posts, in articles, in talks.  Tell stories.  Show people people how much better it is this way.  Be so magnificently effective and mysteriously influential as a senior IC that all the baby engineers you work with want to grow up to be just like you.

Hope this helps.

charity

P.S. — Oh and stop fretting about “competing” with the 20-somethings kuberneteheads, you dork. You have been learning shit your whole career and you’ll learn this shit too.  The tech is the easy part.  The tech will always be the easy part.  🙂