The age-old debate

What I do have are a very particular set of skills, skills I have acquired over a very long career. Skills that make me a nightmare for people like you.

If that sounds familiar it is verbatim Liam Neeson from the (not very good film) Taken.

You could say that Liam’s character is a career specialist. As a recruiter in my past life, I would have been very excited to hear Liam as my candidate say this during an interview. My clients were paying top dollar to find a highly-distinguished skillset and it was my responsibility to find the people with said skillsets. Specialists typically have an easier time in the job market. They can easily explain what they do, how they do it and point to tangible returns on investment.

But does that mean it’s inherently better to specialise?

Working in recruitment put me at somewhat of a loss as to what I could personally achieve in my own career path — realising I was becoming a specialist in recruitment and none of the other disciplines, I decided to pack my bags and gain some of those other skills elsewhere. Leaving behind what could have been a very lucrative path as an executive search consultant for top technology startups (a specialist field at the time). I didn’t see this particular specialist path as the one for me.

But as I’ve learned in that time, you can apply specialist knowledge, in other contexts, and recreate some of the benefits of both sides. Definitions of what puts you in one camp vs the other are too binary:

Most careers oscillate between the two or sit somewhere in between. However for today, I’ll look at each paths objectively as the debate continues to explore them as two opposing paths.

Keep reading for the benefits and constraints of each and lessons to take home and apply in your own career.

The Case for Specialisation

Specialists tend to focus on something and go deeper than a non-specialist ever could. Think Phd researchers, quant analysts in hedge funds, neuroscientists working on children’s brain developments… anyone whose work has clear constraints where recognising patterns is of extreme benefit.

Such individuals have the opportunity to turn their work into a true craft thanks to their repeated exposure and learning — what Malcom Gladwell has termed the ‘10,000 hours’ rule. With such dedicated learning periods and continued advancement, specialists soon achieve mastery.

Focusing on a profession where you can become the best, can make you priceless.

Mark H. McCormack wrote a story in his book ‘What They Don’t Teach You at Harvard Business School’ that always struck me:

It always reminds me of the story about the woman who approached Picasso in a restaurant, asked him to scribble something on a napkin, and said she would be happy to pay whatever he felt it was worth. Picasso complied and then said, “That will be $10,000.”

“But you did that in thirty seconds,” the astonished woman replied.

“No,” Picasso said. “It has taken me forty years to do that.”

A lifetime of applied repetition can produce exceptional results.

Specialists (like Picasso and Liam Neeson) know their worth.

I saw it first hand working in executive search. We described our work searching for the ‘needle in the haystack’ and ‘leaving no stone unturned’ to find the best candidate for the role at hand. I’d spend each day researching, approaching, and then speaking to career specialists who were able to command salaries significantly higher than your average professional ever could. Such people were always headhunted into their next gig, being such a hot commodity, companies would pay to poach them as their own.

Assuming that their particular specialism was part of a growing industry their market value would only soar year on year. According to a HBS study, more than a third  of employers identified work experience as the most important qualification for evaluating candidates.

It’s a somewhat lazy hiring tactic, and I don’t believe always the best, but it continues to pervade in recruitment circles.

In other parts of life, incredible opportunities tend to present themselves to those who are widely known as the best. Think of the conference producer seeking speakers for their next event, journalists seeking an expert opinion, documentary filmmakers choosing subjects to study.

Most of these opportunities got to specialists.

They are well known to be the best in their field, and it is easier to tell a career story and become recognisable when that is the case.

Specialists are also able to build skills and knowledge that benefit from compounding over time. Compounding is considered the 8th wonder of the world and whilst this is in reference to financial compounding, I see it in careers of people who have stayed in their lane and generated more and more expertise on a specific domain it becomes solid grounds for another kind of wealth-creation.

In my last two posts I’ve waxed lyrical about the power of focus — doing less, better. It’s true that without being a specialist, you’ll never have the time or opportunity to rack up those 10,000 hours.

Depth can provide access to these privileges and opportunities in a way breadth rarely can.

Even if you don’t consider yourself a career specialist, you are probably a specialist in another domain of your life. Perhaps an expert on your husband, your friend or your mother… you just know exactly what they will say or do in response to any given situation. Their reflexes have become your own.

However one of the arguments against specialism is that of holding too much bias.

But could our pre-conceived judgements be placing limits on our work, our partners or our own learning? You can be limited by your experience — expecting and searching for something to happen precisely because you’ve seen it before.

This is the core thesis of ‘Range: Why Generalists Triumph in a Specialized World’ in which David Epstein’s favours being a career generalist.

He claims many specialists never see the wood for the trees thanks to their narrow focus. The book includes examples of when experts had said that something wasn’t possible how it then happened 15 percent of the time. Times when an expert predicted an event was definitely going to happen, 25 percent of the time it never did. Source.

Let’s explore what Epstein, and other proponents of being a career generalist, have to say.

The Case for being a Generalist

Who are these ‘Generalists’, exactly?

Generalists come armed with a variety of skill sets. Typically, they are more adaptable, lateral thinkers who can do well across multiple functions or subject matters.

In her TED Talk that’s racked up over 8m views, Emilie Wapnick tells her story of how during school she noticed she enjoyed all subjects equally. This continued as she grew up; becoming all consumed in a topic for a period of time and getting really good at it, before getting bored about the lack of challenge remaining and moving onto the next. She’d repeat the pattern again. And again. This pattern caused some anxiety about forging a career path around such disparate skills and interests.

The notion of a ‘narrowly focused life’ is highly romanticised and there’s an aspirational idea of having one true calling in life. Those who don’t can feel as though there is something wrong with them, but instead, as Wapnick argues they are ‘multipotentialite’.

In Range, David Epstein doesn’t see as reason for shame in variet.

He looked at the data — Nobel prize winners were 22 times more likely to have other skills, specifically like performance: amateur acting, dancing, magic etc than their non-Nobel Prize winning peers.

Epstein turns much of the conventional ‘10,000 hour rule’ career wisdom on its head by citing examples of many successful people who began their career in a ‘sampling’ period of moving between disciplines —thus amassing a broader range of knowledge and expertise. It was from this place they were able to see novel insights or gain a stronger understanding of their respective fields.

He argues that specialist thinking encourages learning from direct experience but severely fails when it comes to learning without experience — basically any kind of hypothetical problem solving, lateral thinking or conceptual reasoning that most careers in the modern world require.

The uncertainty in which we live demands that ideas are connected and work across different contexts.

Startups especially, can benefit from generalist skills and thinking. By definition, startups are about experimentation and testing. Former Google CEO, Eric Schmidt said in reference to hiring during the early days, “a smart generalist doesn't have bias, so is free to survey the wide range of solutions and gravitate to the best one”.

The careers paths of those who pursue life in a ‘rocket-ship’ startup often benefit greatly from a wide range of exposure to different business needs and functions.

Angel Investor and Tech operator Helen Min tells of how Dropbox ran the Dropbox Rotation Program when they were a younger business. The programme took new grads from top schools into a two-year generalist business rotation spanning Customer Support, Sales, and Marketing. The idea being many of the brightest minds don’t know what they wanted to do yet and it proved to be a win-win for the employees and Dropbox alike.

“If you’re offered a seat on a rocket ship, don’t ask what seat!
Just get on.”

— Sheryl Sandberg

When the future is unknown as it tends to be in startup land, a range of skills and aptitudes fares best. You can jump into a new team or department depending on business goals and focus and achieve inter-disciplinary mastery that bridges communication and skills gaps between teams.

It’s not just startups that think this way. In 2016 HBR posited that “Generalists get better job offers than specialists” where Investment Banks hired MBA grads, Generalists had higher earning power.

If this is all sounding like the news you needed to hear today, you’ll want to check out Generalist World, a community that could be for you.

Founded by Milly Tamati it addresses the growing appreciation of generalists in the workforce and sources job opportunities for generalists who ‘don’t fit into a neat box’. In less than 3 months they received 1000s of applications from people who felt seen by what Generalist World stands for and employers are finally taking notice.

Generalists are not hampered by their multiplicity it seems. It is in the blending and colliding of insights, skills and experiences that new ideas emerge.

It is precisely because generalists have been so underrated for a long time that these communities, research and programmes are needed. Generalists have been underestimated because the path of the specialist is a more well-trodden and simple one. The specialists may experience their own down-falls but in public consciousness they will continue to gain status and awards for their expertise for a long time to come.

The call for alternative frameworks

There are better and alternative frameworks and ways of thinking about the generalist v specialist debate — of course everyone exists somewhere on a spectrum.

Figuring out a framework that makes sense for your own career path depends on your answers to questions you can start by answering.

Questions such as:

• What are your natural tendencies and curiosities? Do you tend to be interested in a little, or interested in a lot?

• What are your hard skills — do these lend themselves to a career as a specialist and seek a unique advantage others might be able to?

• Whose career path do you admire? Likely you’ll find clues about your own in your answer.

• Are your core strengths and interests relatively overlapping, or more disparate?

• Do you have a preference for earlier stage or late stage companies?

Your answers to these questions will lend themselves to a better option for you, uniquely. Which is ‘better’ is subjective. However this is a newsletter for people in entrepreneurial career paths and many of you will resonate with the generalist tendencies.

Traditional employment opportunities tend seek candidates who fit neat job descriptions and make it hard to find exciting, challenging roles that span problems and disciplines which is the entrepreneurial preference.

It’s precisely why so many ambitious, entrepreneurial folk turn to entrepreneurship or portfolio careers as a necessary alternative to a stifling job. You really do get to wear all the hats in companies of one. You get to wear a lot of hats in early stage, undefined startup environments too.

If you resonate with being more of a generalists, do ensure you avoid the following traps at least:

• The trap of not having a core mission, value or strand that ties your experiences together. Don’t let your path become completely random — it’s hard to achieve big goals or become credible unless you stand for something or have navigated similar environments and problems.

• Leaving in the 'dip’. All careers and businesses have their hard challenges to overcome — but don’t keep moving to the next thing when it gets tough. You need to master a skillset or problem rather than following the next shiny object as soon as times get tough. Build a skill of overcoming adversity, too.

• Frequently changing your role function AND the industry. It is better to move across different functions within an industry, or move industries and stay the same function, but doing both frequently removes any chances of building that all-important compound knowledge.
  P.S. during a career transition you will likely change both, which is cool, and encouraged during a pivot. Just not every time ideally.

• Expecting to be good at EVERYTHING. The best generalists know they need to double down on a few core areas — seeking out skills and areas that are mutually beneficial and together can make you stronger.

My personal preference is to focus on becoming excellent at a combination of 2-3 valuable skills.

“If you combine two skills that are valuable, but even more are rare and therefore more valuable together …automatically you have a competitive advantage that lands you in the top decile of earning power.”

- Tim Ferriss

Applying the benefits of depth and expertise from a particular domain or skill, to another one or two, can stand you out from the competition but allow you to sell yourself as the ‘best’ in a given field.

I’m developing strengths in coaching and content creation and know there are no jobs that would pay me to do this, I have to do it myself.

Other examples include the

• Designer who picks up skills in development and copywriting to build websites

• Artist who picks up skills in photography and motion graphics to bring visual exhibitions to life

• Sales person picks up skills in management and psychology to lead powerful sales teams

You can mix whatever traits and skills you choose — just have a reason for it.

How are you thinking about your career path framework? Which shapes or definitions come to mind, if any?

Let us know in the comments.

In two weeks we will be joined by Sarabeth Berk, TEDx speaker and expert on professional identities who observes there being a third, invisible option in this debate: the hybrid professional. This is an identity many don't realise is available and can be transformative when its understood and explored. I’m excited for you to hear from here.

Before you go — know that if you are feeling overwhelmed and in need of a plan for the next phase of your career with bespoke frameworks and guidance — The Ask® coaching can help:

1. Decide and commit to what’s next in your career

2. Make a plan for what’s needed in terms of your time money and resources — having it project managed and mapped out with you

3. Stay the course. Holding you accountable to this plan and overcoming obstacles along the way

Click here to book your complimentary consultation and make a game plan for your career 2023.

Thank you as always for reading!

Ellen Donnelly, Founder + Chief Coach, The Ask.