Advice That I Can't Get Out of My Head

If you want to spend years in high growth environments, and reap the benefits that that growth entails, it’s essential to make sure that you are learning at least as quickly as your role is growing if you want to keep your job.

You can get a coach, find mentors, take classes, read, listen to podcasts, or pursue any number of other different ways to learn – the right learning strategy is the one that you’ll actually follow through on. The path that I’ve invested in the most was reading, particularly reading as much as I could about business and scaling high growth tech companies.

Across all of the reading I’ve done over the years, I’ve come across a few pieces of advice that I haven’t been able to get out of my head. These slices of wisdom have been immensely helpful to me and I wanted to share them both so that others can benefit. I’ve found all of these observations to be:

  • Actionable: They’ve given me something to emulate or avoid, or helped me to detect signals that might otherwise have blended into the background.
  • Insightful: They represent a truth that I probably wouldn’t have reached from my own observation, other than perhaps by dumb luck.
  • Trustworthy: I’ve been able to actually see examples of these phenomena in real life.

Let’s dive in.


This X post by Emmett Shear (most famous for being CEO of Twitch) had a huge impact on how I think about burnout.

Emmett describes 3 main causes of burnout (paraphrased):

  • Permanent On-call: Never having true time off, because work can always reach you (or in the case of very intense jobs, because the work never actually ends). I had always considered this to be the only real cause of burnout.
  • Broken Steering: Shear describes this better than I could, as “that feeling at work where your actions seem to have no impact. Turn the wheel, car still goes straight.” This causes a deep emptiness in the day-to-day of your job.
  • Mission Doubt: The feeling that your work doesn’t matter, typically because you don’t actually need your job to survive.

Why I love this advice:

I’ve worked in startups and scale-ups for a long time. Both of these environments are rife with burnout (at every level of seniority – many junior employees don’t realize how burnt out the execs around them are, because good execs are excellent at maintaining an emotionally positive veneer). Managing burnout is essentially a critical supply chain problem for knowledge-work businesses, and you need to be able to identify and address it both in others and yourself.

This post really captures the phenomenon of burnout well, and elucidates several patterns that I had observed but couldn’t explain:

  • I had seen people getting burnt out despite meaningful separation from work – vacations weren’t helping. In retrospect, this was a classic case of Broken Steering and/or Mission Doubt.
  • Some people appeared to be essentially burnout-proof. In a few cases, I observed people working for years with near-permanent on-call and consistent 60+ hour weeks (with spikes to 80+), including through major events like weddings and honeymoons. They appeared no worse for wear than others working half as much.
  • Product managers appeared to be at significantly higher risk of burnout than engineers – even when engineers had more on-call responsibilities. In retrospect, I think that this was a classic case of PMs experiencing Broken Steering at a significantly higher rate. Every time you compile your code and watch it run, you can feel the steering working.
  • I noticed that many parents of young children, despite having significantly more on their plates, seemed to get burnt out less. I even noticed this in myself, and didn’t have a real way to explain it – my first kid’s birth coincided with the busiest working period of my life (do not recommend), but I found that I had a more positive attitude towards work, for no reason that I could really explain. When I read this post, it all clicked – when you have young children Mission Doubt entirely disappears because you need to feed them.

How I’ve found it useful:

Preventing burnout is extremely valuable if you’re scaling a company. The types of employees who get burnt out are often tenured, hard-working, and outcome-oriented – exactly the people whom you want to make as happy and productive as possible. This advice led me to actionable steps that I could take as a manager:

  • You can improve Broken Steering somewhat through immediate, direct positive feedback. That meeting was really well run, thanks; This doc really explained the situation well and we made a better decision because of it; I use that report every week to prep for our executive readout, I appreciate the excellence in putting it together. This isn’t perfect but it helps and requires virtually 0 marginal effort.
  • You can also improve Broken Steering with a culture of quantitatively measuring small wins.
  • Broken Steering gets a bit better just from being aware of it. You send the email, get no immediate feedback on whether it mattered – but if you don’t have the expectation that you’ll get an immediate rush of success, it tempers the feeling of a broken feedback loop. This is vital because executives are very susceptible to Broken Steering since the majority of your output is executed via your team.
  • Mission Doubt is a bit harder, especially if you’re making business software and don’t have a grand, civilization-transforming mission. But instilling a shared sense of purpose, tight-knit teams, and a sense that the company as a whole is making progress (even in the vague and potentially silly sense of getting to a fundraising milestone) can all help.
  • Mission Doubt can also be improved by meaningful equity ownership. I’ve rarely seen Mission Doubt in people who felt that they had a reasonable shot of making enough money from equity to put a down payment on a 3 bedroom home in a good school district.

SaaS Competition

This is my favorite post about why competition in SaaS tends to be so ferocious. SaaS is my trade and this post captures the underlying dynamics extremely well:

  • Many SaaS sectors turn into winner-take-most oligopolies – the highs of winning are higher and the lows of losing are lower.
  • The leaders of SaaS markets are incentivized to compete with one another in an uncompromising manner. There’s no dynamic like the one between Google and Apple, where YouTube is one of the most important apps on the iPhone – SaaS companies wage total war on one another (Lemkin refers to this as “dominant strategy”).

Essentially: SaaS markets are brutally competitive, and the way that they’re won is by competing brutally.

Why I love this advice:

There’s a lot of confident advice out there that competition doesn’t matter – don’t think about anyone else, just hit the gym and focus on yourself, king. The reality is that SaaS companies are natural predators of one another, and the only thing that you accomplish by ignoring this reality is make yourself a fatter target.

The advice to ignore competition seems to come from consumer monopolies that simply don’t have natural predators, especially Google (at least until recently). In my opinion, ignoring your competitors is some of the worst advice around. All of the best startup leaders I’ve met are highly attuned to their competitors’ moves, and the others get eaten alive. Zuckerberg famously is a total psycho about competition.

How I’ve found it useful:

SaaS competition always inevitably develops into total war:

  • Everybody wants to grow
  • You’re all fundamentally fighting over the same dollars
  • Those dollars are smart and mobile
  • SaaS companies are very stable

As a result, everyone is fighting for every dollar on the table, and there’s rarely a natural tipping point where the competitive field simply collapses (as one sees in marketplaces or consumer social). In order to win, your product, marketing, sales and even customer support all need to be fully engaged for years on end. A culture of excellence is required to win in highly competitive markets, and in many ways you’re only as strong as your weakest function.

If you’re at a large company, it’s easy to view competition as someone else’s problem. At a startup, it’s everyone’s problem.

Trusting Your Gut

My favorite advice about the role of feelings in decision-making is this short Quora post by Auren Hoffman (founder/CEO of LiveRamp). The concise summary of the advice is: “You should trust your gut to avoid things, but you should use data to decide to take action.” I’ve always interpreted this to mean that you should trust your gut to tell you when there’s danger, but you should not trust your gut to identify good opportunities. The post also includes the amusing and memorable implication that the reason you can trust your gut to detect danger is evolutionary: Essentially, everyone with weak genes for detecting hazards was eaten by some carnivore millions of years ago.

Why I love this advice:

The idea of trusting your gut to avoid bad situations is similar to the canonical description of street smarts. Street smarts aren’t about the good situations that you seek out based on your gut; they’re about the bad situations that you never get close to in the first place.

When I first read this advice, I basically had the thought “huh, that sounds reasonable” and filed it away. But I’ve since seen it recur over, and over, and over again.

How I’ve found it useful:

I’ve found this advice very empowering because it gives you permission to be illogical. It’s so tempting in a quantitative field like tech to desire to be hyper-logical in all things: Everything is a spreadsheet model or a SWOT analysis or a data dashboard.

I’ve often used this advice to get myself over the hump of bailing out of a bad situation, and in every case I’ve been happy I did. For example:

  • This candidate is great on paper and had glowing reviews on their technical skills, but there were a few small flags that make me doubt their character.
  • This feature seems really useful, but I feel like it’s going to make customer uncomfortable from a security point of view.

The Durability of Leadership

The book Extreme Ownership was written by former Navy SEAL officers about their experiences leading teams through some of the most intense battles in Iraq. One of the authors is now a famous podcaster, (Jocko Willink), and their team included the American Sniper and the real-life Most Interesting Man in the World.

About halfway through the book, the authors describe an experiment during Navy SEAL training where they swapped the leaders of their most successful and least successful teams. The surprising result of this experiment was that both teams excelled after the flip, because:

  • The weak team now had a great leader who elevated their performance
  • The strong team maintained a durable culture of excellence

Why I love this advice:

I can’t describe how often I’ve seen this phenomenon in real life. Teams that have had good leaders just run better – they make better decisions, they are more resilient, and perhaps most importantly, they have higher standards for others and themselves. Teams that have had poor leaders are predictably the opposite. They take longer to get less done, and more disappointingly they often have a bitter attitude. Leadership quality is durable and highly contagious.

How I’ve found it useful:

This chapter made me internalize the urgency of investing in establishing strong leadership for all teams, and the urgency of stamping out bad leadership when you see it. This advice helped me understand the value of promoting and firing faster.

Great leadership is also the best way to build organizational resilience. Bad things happen to startups all the time. At one point I briefly kept a journal of when I felt like we had a disaster during the startup journey. I gave up after about 3 weeks because we were having a disaster roughly every two days, and the exercise was feeling depressing and pointless. Great leadership gives teams the ability and self-belief that they can weather this constant storm of challenges.

Final Thoughts

When reading any advice, including the advice above, I think it’s really important to apply a critical eye. If you’re curious you can find our advice broken out by category here, and we welcome any and all feedback that you have issues with based upon your experience.

So much advice out there is actually highly context-specific but presented as universal. What I love about all of the advice included in this piece is that I’ve been able to see all of it in action myself.