Discover more from Stay SaaSy
Build Your Career on Dirty Work
The Dirty Work Theory: The lamentable work that many people avoid are great places to look for high impact, low hanging fruit.
Whenever people ask me for advice on career growth, I share what has worked reasonably well for me: find a growth company, one that really needs you to get work done, and then tackle the unpleasant work that everyone avoids. I think this is a broadly applicable path:
High-growth matters because at an exponentially growing company you’re first in line for exponentially more (and larger) opportunities. When growth is high you also win by doing, rather than winning by getting ahead politically.
Being at a place that needs you to get work done is essential - the more they need you, the more you’ll have a whole community of people trying to help you crush it.
The final bit is often the most surprising - look for the nasty things people avoid.
This is, notably, not the path that many seek out for career growth:
FAANG companies and very early startups (not yet in growth mode) appeal to many early in their career because they offer the highest rewards in terms of expected compensation, brand value, or potential upside.
Often, the sexiest high-growth companies are over-hiring – they don’t truly need you. Think of joining Coinbase pre-layoffs.
Many (if not most) people instinctively want to do cool, novel, flashy stuff. Create a new cryptocurrency, prove P != NP, make a sick beat, ..etc.
Let’s zoom in on cool vs uncool work. The first reason that you should be looking for lamentable challenges is that the less people trying to do something, the more low hanging fruit there is.
For every awesome frontier, there’s a bunch of awesome people who have tried a bunch of awesome approaches. You’re not going to find a super-easy, big win in that environment. On the flip side, the more unsexy the work is, the less likely it is that a lot of really great people have taken a crack at solving it. In short, there’s likely to be low hanging fruit.
However, it’s important to not only find low hanging fruit, that fruit must also be worth picking.
The second reason you should look for this kind of work, is that any work that is bad enough that it’s got a reputation, or that it’s the topic of commiseration, is something that is high impact if you can fix it. Making a whole bunch of people’s problems go away is a big win no matter where you work and no matter what the thing is. Much like the classic movie Field of Dreams, imagine there’s a little voice whispering to you: Ease Their Pain.
Let’s look at some examples and talk about how to approach them.
Examples & Solutions
If you work at a software company, there are some pretty common categories of work that people often avoid, including:
Support of the product
Administration / Bookkeeping / Documentation
Apologizing to angry customers
Training your sales team
Researching the competition
Writing high-quality documentation
Answering product questions from internal teams
All of these are great places to look for high impact opportunities. Often people look at these difficult business domains as intractable problems. One signpost for high-value dirty work is persistent proposals to hire a team that will make the problem go away (often in someone else’s department!): “we’ll always have pages, we need to hire a NOC”; “you can’t make support tickets go away, we need to hire a support team”; “we need to just rewrite”; “we need to hire QA”.
And listen, at a big enough scale you might need to hire these things. But this advocacy is often done too early and with too much fatalism. We’ve been to the fucking moon y’all, we can figure out a way to halve our Series-A-sized support queue.
Once you’ve found an opportunity, put yourself in the firing line: go on-call, do support, do QA, do the tech debt. Take on the pain. Then fix it.
A warning: do not, in any circumstances, normalize the pain you’ve accepted. You must fight tenaciously to fix the issue. Embrace the dirty work, and then be the leader who solves it comprehensively and scalably.
Many people try to avoid on-call. Or, they try to “get through an on-call week”. On-call, like all of these problems, is a place for making big impact. And you make on-call better by leaning in, not avoiding it.
An aside: a particularly problematic subset of on-call avoiders is managers, often under the pretense of not knowing enough about the system. If this is you - you’re playing yourself. Feedback is a gift, and on-call is managing feedback from your system. One of the absolute best ways to learn about a system and identify opportunities to fix that system is through on-call. Especially if you’re an engineering manager, get into the on-call rotation!
So you’re in the on-call rotation, now what? Make pages approach zero. You can do it. Trust me, you can make pages trend towards zero. Many have done it on teams at the highest-scale companies in existence.
In my own experience, I once entered an on-call that looked like a warzone: tired eyes, frayed nerves, resentment and blame. And instead of solving the problems with just more bodies, we worked smarter and harder. We made product changes, added limits, automated runbooks. We didn’t get pages to zero, but we got it much better, all through continued hypergrowth. I learned a lot about the system, and I had a major impact. In fact, my biggest regret is that my team and I didn’t go on-call sooner.
Another place people often overlook is QA, particularly QAing other people’s work. I love QAing other people’s work - it’s one of the best ways to learn about the product and to prevent issues from going out.
This is another place where managers are often silly to avoid. Woe is the manager who doesn’t know squat about their product. Woe is the manager who can’t improve quality on their team. Tactical applications of QA can be one of the best levers for managers to ensure they’re in the loop and manning the fort.
Often people don’t give QA a chance - they often think it’s monotonous monkey work that should be farmed out to a different team. This is very false: only boring people are bored and only bad QA is monotonous. Implicit in this anti-QA point of view is one of the most common traits of lamentable work – people don’t do it well, but don’t believe it’s a worthy problem to focus on getting better at. When this catch-22 is raised, people sometimes flip the script and talk like QA is some magical language they couldn’t possibly get good at. Notice that these arguments don’t come up when the same people are up to learn about new fancy stuff, like distributed systems or web3.
In any case, proper QA requires major amounts of critical thinking, systems understanding, and creativity. And you learn it! Good QA builds automation, forms sophisticated risk profiles to weight work, and often requires deep understanding of human bias and behavior. And the best QA builds a set of expectations, metrics, and enablement so that an entire team can ship both faster and higher quality. The best QA also serves as a feedback cycle into building better. And similar to reducing on-call pages, great QA also helps your team build faster, and building faster will help your career in other direct and indirect ways.
Oh, and Companies Too
Not only can you build your career with dirty work, you can also build a company on it! Some of the best companies are known to solve the boring, lamentable problems of other businesses. Zapier and Stripe are great examples of businesses that have solved boring problems in extremely impactful, and profitable ways. In fact, much of the best B2B software seeks to solve the most acidic above-the-shoulders mustard work there is. Sometimes dirty work looks a lot like a unicorn startup.
Dirty Work isn’t for everyone. In fact, the absolute best of the best often do whatever they want and are brilliant at it. There are people like Steve Jobs out there who rise above all the rest of the excellent people who are trying to do similar things.
But for every Steve Jobs, there’s a Tim Cook. Tim Cook was an operations-heavy executive who didn’t do a single cool-commercial-worthy thing in his entire career before becoming CEO of one of the most dominant tech companies in the world. And then he made that tech company an order of magnitude more dominant. He cut his teeth on the dirty work, and as a company gets larger and larger, emphatic delivery on dirty work is the skill that becomes more and more valuable.
The final thought: becoming an expert in dirty work is wildly differentiating. The more you learn to navigate the messy, human, frustrating problems that everyone else avoids, the more you see the forest for the trees, the more that ability shines a light on a whole host of issues that seem totally broken and wildly tractable.
When it comes to technology, I’m no Steve Jobs. But maybe one day I’ll be a Tim Cook. It’ll take a lot more Dirty Work to get there.