Career Advice for Ambitious Generalists

This is the long form of a social post a number of people told me was helpful. If you prefer a shorter version read that first.

In the early 1480s, an Italian polymath applied to a job in a duke’s court. In his application, he listed his abilities as a military engineer, including plans for building portable bridges, removing water from moats, digging secret tunnels; designs of types of cannon, armored tanks, and catapults; not to mention proficiency in architecture, construction, and hydraulic engineering. At the end of a long, rambling 10 point list, he casually mentions he can do sculpture and “likewise in painting, I can do everything possible as well as any other”.

Imagine receiving that job application. Would you hire that person? His claims seem impossible, or at least impractical: no one person can be good at all of those things. Indeed, it took several years for him to gradually gain commissions to work on military engineering projects, and most of his designs were too impractical to be built or implemented. Eventually, the French invaded without facing much resistance, and he lost his place at court.

Now consider the job application he could have sent:

“I can paint. See below:”

As you might have already guessed, the long, rambling job application was written by Leonardo Da Vinci, one of the greatest artists, inventors, and engineers the world has ever seen. He really was good at all of those things, and more. He also conducted detailed studies of human anatomy, designed a primitive form of helicopter, and his studies of the flight of birds led to early concepts in aerodynamics. However, most of his mechanical designs, artworks, and scientific studies were never finished, and were only later rediscovered through his comprehensive notebooks.

If you’re a self-confessed generalist, you’re probably feeling pain right at this moment. You probably don’t claim to be as talented or prolific as Leonardo, but I bet you have several unfinished product ideas, creative projects, and blog posts stuck in your Notion database. Like Leonardo, you struggle with deciding what to work on, and how to describe yourself to others. You always manage to earn just enough money to indulge your creative urges, but you never focused on one thing long enough to earn financial freedom.

T-Shaped Individual

Ambitious, creative people are usually generalists, but clients and customers want to hire specialists. Your choices are the specialize and live a boring, unfulfilled life, or stay generalist and therefore generally unemployable. The ‘T-shaped’ concept was an attempt to solve this problem: choose one specialism to become an expert in, while indulging your interests on a broad spectrum of other skills. However, I found as my career developed I could never stick to one thing: as I jumped from skill to skill my T turned into an M, then eventually an amorphous blob.

The smartest, most ambitious people I’ve met are all badly affected by this. In fact, the more ambitious and creative you are, the more it seems to hold you back. Nobody wants to hire an ‘ideas guy’, they want you to execute on the ideas they already have. To the point were many of the most talented people I know actually can't get jobs without moving into senior management (where being a generalist is tolerated), or starting their own company. The problem is when they start a company they now have to figure this out for their company, or it'll suffer the same fate.

The Shoggoth Strategy

The Shoggoth Strategy works by hiding your messy generalist experience behind the friendly face of specialism. A Shoggoth is a fictional creature from the novels of H.P. Lovecraft. Massive, blob-like monsters made out of iridescent black goo, covered in tentacles and eyes. That represents all your myriad skills and interests, and you need to hide it away. Stay generalist, but just hide the crazy for the first few dates. Choose one specialism that’s always the first thing you talk about when meeting people or writing copy for your landing page. If they’re going to remember one thing about you (and you’re lucky if they remember one), what should it be?

Hiding My Shoggoth

Let me give you an example from my career:

After graduating with a Masters in Economics at the height of the 2009 global finance crisis, an enterprising recruiter sold me on a career in digital marketing. I was running Google Ads campaigns, spending $10m per year so I quickly built a deep specialism there. Then Facebook Ads became the hot new thing, so I jumped ship to an in-house job at a travel company, where I spent millions of dollars back when CPMs were cheap and you could run a lot of experiments. Growth hacking became a thing, so I started to learn to code and landed a product management job A/B testing landing pages, optimizing SEO content, and analyzing email sends.

All of this experience gave me the well-rounded skill set I needed to start my own marketing agency, but I had a problem. I had moved to New York and was going to a networking event every night, having mediocre conversations that never led to clients. Every conversation was on a different topic, and people were always too confused about what I did to make referrals. Finally, I mentioned to someone I had spent $50m on Facebook ads and his jaw hit the floor. He immediately asked if we could meet for coffee, because he was struggling with his Facebook ads, and wanted the opinion of an expert. He also referred two people he knew who also had the same problem, both of which became clients.

I didn't hide my other interests, I just started started telling people what I did was Facebook ads when they asked. The follow up question would be querying my experience, which is when I'd drop the $50m ad spend figure and close a coffee meeting or referral, which led to clients. I had found a credible entry point, a simple fact about me that I could drop to gain instant credibility. People started referring me to their friends, because they could easily recall what I did, and when somebody might need my services. Whenever they heard something interesting about Facebook Ads, they’d get back in touch to get my opinion. I was the ‘Facebook Ads guy’ in their network.

Once I landed a client, over time they'd also need some of my complementary skills, like setting up tracking, writing copy, or designing creatives, all of which I liked doing. This was my T-shape, or at least it looked that way to them. As I built trust, they'd also ask if I did Google ads, or we'd do some advanced analysis with data science, and start A/B testing landing pages for them. Smart sales people call this 'land and expand': get your foot in the door, then upsell. My Shoggoth was well hidden behind the friendly face of my Facebook Ads specialism, and would only be incrementally revealed as trust grew. I never dropped my other interests or even worked on them less: I remained a generalist, but with the benefit of specialism.

Hiding My Company’s Shoggoth

Eventually I grew the agency to 50 people and we came to the realization one day we had to lay 14 of them off. We had always been tenuously profitable at around ~5% margin, so a weak sales quarter and losing a couple of key clients was all it took. We had grown by cell division: basically hiring clones of me. That meant we had built a team of generalists, and all of their Shoggoths were showing, scaring the clients. I came back to the Shoggoth strategy, but this time applied it to my company instead of myself. We called it the ‘Avengers’ model: each team lead had their superpower, but had enough hidden depth to carry their own franchise (p.s. I know Gamora isn’t an Avenger – people picked their own and I let it slide).

It worked: Profit margins hit north of 20% within 2 months, and we got back up to 50 people a year later. We had turned every role into a specialist one, so that clients would build a package from an a-la-cart menu of specialisms, including Facebook Ads, Google Ads, Conversion Optimization, Ad Creative, etc. Small businesses and startups might see ‘marketing’ as a specialism, but enterprise clients have enough scale to keep whole teams of specialists busy. When you can afford millions of dollars of Facebook Ads budget, you want the best people at Facebook Ads, not someone who does it part time.

We did lose a few of our best generalists when we made this switch, but we quickly replaced them. The people we hired to replace them identified with a specific specialism, and therefore staff attrition went way down: once you start building your identity around Facebook Ads, there are only a handful of companies in the world that are worth working for. To keep the Shoggoths happy we allowed moonlighting and side projects, as well as encouraging transfers between teams and upping the learning budget. Clients were getting the specialism they craved, and the Shoggoths were well-fed and hidden. Your company may do many things well, but you can benefit from putting your most credible specialism forward across all of your marketing material, and in your sales pitch. If you really can’t choose, do what we did and offer different departments to your clients, so they know what categories they’re buying.

Why Hiding Your Shoggoth Works

The gelatinous blob of generalist skills you've accumulated, the Shoggoth, is complex and scary for people to process. Nobody believes you can be good at everything. Some people actually are polymaths, like Leonardo Da Vinci or Elon Musk, but it bruises our egos to admit that fact. We make excuses and imagine tradeoffs that explain our lot in life “I could have made it as an artist, but it was more sensible to study mechanical engineering”. Them when some renaissance man comes by who can do both of those things (and more) better than you can, it bruises your ego.

There's another reason specialism wins: people allocate way less time to hiring and buying decisions than you might think. You're extremely lucky if they remember more than 1 thing about your company or personal brand. As Peter Thiel says, most companies fail, which means they didn’t get a single thing to stick: "If you try for several but don’t nail one, you’re finished”. Studies show any additional interest you communicate only dilutes your message, and attempting to communicate more than 2-3 messages increases the chance they won't remember anything at all about you. This is why most consumer brands spend millions just to get to you form one memory association (i.e. ‘Lucky Strike is toasted’). You need to earn what Warren Buffet calls “share of mind”, so that when they think of a category they think of you first.

There's a double penality to being a generalist, which is that as well as conversion, it also decreases word of mouth. There's way less chance someone will remember to refer you to their friends or coworkers when there's an opportunity to, if it's not crystal clear in their mind. Even if you are referred to someone, there's way less chance they'll call you if you don't fully identify with the category of job they need doing. You call for a plumber when your pipes are leaking, not a handyman. Everyone focused on gaining credentials, but simply identifying with a single category can be enough credibility – they ask “is anyone a doctor!?” when someone is sick on a flight, not “did anyone here go to an ivy league medical school?”. In memetics terms, we use someone’s identity as short-hand for evaluation, and if it’s not immediately clear what ‘memes’ this person is identifying with, it causes memetic confusion and doesn’t stick in our memory.

Finally, think about competence. If you spend six months learning one specialism, you’re going to be six times more competent at that individual skill than someone who did it for 1 month, then pursued 5 different interests. We found this with our staff, who basically couldn’t hold their own with clients until they had done 6 months of deep work in an area. This is particularly important for people early in their career, when most of how to get ahead is a confidence game. Unless you’re naturally confident, you can earn that confidence through competence, and that requires soaking yourself deeply in a domain. Because of the 80:20 rule, you can usually get to ‘good enough’ in any field in a surprisingly short time, particularly if it’s the first thing you talk about. You learn the ‘memes’ that practitioners are supposed to know, and no longer trip the bullshit meters of people with any experience in the field.

Theres More Room at the Top

The main force pulling in the other direction towards generalism, is that most people hate to focus on any one skill for a long time. It gets extremely boring. Anyway the reason you’re so creative and productive, is because you have a variety of interests that weave together in unpredictable ways. Variety is the spice of life, and you don’t want to be always talking about Facebook ads, or whatever specialism you choose. However, if you don't do this you'll always be broke, unable to get the best jobs, or to grow your company. You can afford a lot more spice in your life when you're making good money, just live your generalist life with your real friends, behind the veil of specialism you adopt for clients.

For companies, this means staying extremely disciplined. You know you should specialize, but it's really hard to turn down revenue when someone offers you something outside of scope. I did the same thing and it took me 5 years of struggling trying to go my agency to learn this lesson. One day I read an article that said Uber was doing 7,000 conversion optimization tests per year. Across our whole agency, across 5 different channels, we had only run just over 1,000 tests that year. If we had just focused our credibility on one specific area, we might have been good enough to land Uber as a client, and that could be the gateway to more large clients.

Most people never get exposed to the extreme scale of Fortune 500 companies, so they just can't imagine how much room there is at the top to have an impact. So they settle for a small amount of revenue today, and get trapped in a cycle of always accepting things that are out of scope. They don't compound on their specialist skills, and never build a personal brand focused enough to get into the room with the top tier companies. The returns from specialism are exponential: the number one listing on Google gets double the traffic that the second slot, and more than 3x position number 3. If you’re blogging about something that’s not your specialism, you could be diluting your ranking on the one keyword that matters.

I know it sucks that the world works this way, and I'm not asking you to change or drop your interests. Just hide your shoggoth behind the friendly face of specialsm and nobody will know the difference. Perception IS reality, so what you show outwardly becomes a self-fulfilling prophecy. If the first thing you say to everybody is your one specialism, you'll land more clients in that specialism. Then that'll lead to better case studies, and your credibility grows. Eventually it compounds, and you can get your foot in the door anywhere you like. Land and expand. Eventually when you've built up enough trust you can release the shoggoth, just not on day one. If you found this useful pass the advice onto your friends and colleagues. If you catch someone getting too carried away with their generalist interests when they should be selling their specialism, remember to tell them: “Psst, your shoggoth is showing”.