Lesson 4: Get outside your comfort zone and keep learning.

A career is a long journey. I benefited massively from challenging myself in new ways - new roles, new application areas, new industries. This meant I kept learning, developing and expanding my skills throughout my career.

For clarity, this does not mean burning yourself out by tackling massive new challenges every month.  What it means is ensuring you are continually learning in small ways (mostly in or close to your comfort zone), and occasionally have large learning opportunities (outside your comfort zone).  While the frequency varied, on average I’d estimate I had major new learning opportunities roughly once every year.

In fact my primary reason for changing jobs was usually when I felt my rate of learning had slowed down a lot, and the internal opportunities for new challenges were not as exciting as ones elsewhere - so a shortage of things both in and out of my comfort zone.

When I did change job many aspects of both my role and the company itself were dramatically different to what I had done before.  I changed companies about every 4 years, and while I sometimes discussed/interviewed for roles that were similar to what I’d done before, I always found myself  choosing not to do those.

That’s not to say that I consciously understood this “lesson 4” from the beginning of my career - quite the opposite!  But, I like, enjoy, and am strongly motivated by learning new things.  I get a strong sense of satisfaction from developing mastery in new areas. So this path mostly came fairly naturally to me - although of course stepping outside your comfort zone is never easy! This path may not come as naturally to you.  So, why force yourself to step outside your comfort zone? Why is this particularly useful?  Three important aspects come to mind:

Aspect 1: Skill and Perspective development.

Fairly obviously, if you can keep learning, you will develop your skills more broadly and deeply and that typically means you will be more successful at your job, more attractive to employers, and more capable of taking on difficult, high-impact things. However even if you stay close to your comfort zone you can keep learning.  But moving out of your comfort zone accelerates the learning - so that’s good.

A more subtle point is that more impactful, senior, leadership roles require the ability to approach and think about problems from many different perspectives. One of the defining factors of something being outside your comfort zone is the very fact that you don’t have clear, deep perspective on the challenges involved.  And hence the opportunity to learn how to integrate more new perspectives is much higher than things within your comfort zone (almost by definition of ‘comfort’!).

Let me list some of the diverse challenges from which I was able to learn new perspectives. I worked:

• in different industries (mobile games vs grocery retail vs a 3-sided marketplace vs the biggest social media company!)

• in high margin digital businesses and low-margin food businesses

• in different roles (Algorithm Engineering, Data Science, Product Growth, Product)

• in operationally heavy businesses (Deliveroo & Ocado) vs operationally simpler businesses (King). Meta was somewhere in the middle.

• across so many dimensions of marketing, acquisition, retention, subscription, growth, lifetime value, incrementality,…

• in start-ups, in high-growth scale-ups, in one of the global tech mega-corps.

• …

Each of these differences made me learn and appreciate new things and develop new perspectives with which to approach problems. So embrace this kind of diversity, over many years, and you will learn a LOT!

Aspect 2: Have more impact

If you get out of your comfort zone, you can work on higher impact things. A bit of thought makes this obvious: the top 3 most important problems in the vicinity of your role are unlikely to ALL be in your comfort zone (if they are - then great! - tackle those efficiently, perhaps delegate and mentor a lot, and work to think ahead to what should come next).  So, normally at least one very important thing in your vicinity is definitely not in your comfort zone.  If you’re open-minded and willing to take this on, and stretch yourself, you can then have more impact.

There’s not much more to say about this, except to pick carefully and validate that these things really are “most important”.  Nothing worse than thinking you are working hard on a really important problem, only to find it is not. (Unless you are the person whose work demonstrates this new fact).

Early in your career you may need support and mentorship in identifying these things. Great managers will provide that.

Aspect 3: Lead between the cracks

Regularly important problems will fall into an area where the company is currently weak, and/or fall into the cracks between areas (between teams, etc).

Taking on these kinds of problems means providing leadership and if you take them on you will often solve a leadership problem, and be doubly-appreciated for that.  This, naturally, means your leadership/execs think of you as a reliable, important pair of hands.

In my experience, it also means they will have patience when you stumble a bit in tackling the new problem - after all there was no-one else willing and/or better suited to it. And it is a difficult problem, falling between the cracks of the business, so it is natural you will run into some stumbling blocks.

How to decide?

For clarity, getting outside your comfort zone doesn’t mean you tackle anything that comes your way. First, you should focus on important, high-impact things. Second, lean towards things that are exciting & motivating to you - that’ll make the hard times much easier! BUT, if something is critical enough, do consider pushing for and saying yes to things that are perhaps less motivating or less pleasant or even further from your comfort zone.  But even then, I think it is ok to decide that some challenges are not for you. But be careful, you might be missing a great learning experience.  And if you say “no” too often, opportunities will stop coming your way.

My career, on paper, was a series of roles all of which I was super excited about: I love designing algorithms to solve/optimise hard, technical real world problems (Ocado), I loved Data Science (King), similarly for my Product Growth & Product roles (Deliveroo), and then a wonderful, challenging Product leadership role at Meta.  But throughout those roles I often took on some side-responsibilities (and sometimes new primary roles) for 6-18 months at a time which were often in some ways less personally motivating, but also huge learning experiences. I could not have done some of these forever (e.g. I’d have burned out), but they were well worth doing for a while - both for the business impact they delivered and the personal learning involved.

For example, besides my Data Science responsibilities at King for 18+ months I ran the Data Engineering/Data Analytics/Reporting teams.  Both the new technical problems in that area (as Candy Crush grew quickly to 350 million monthly active users) and the team/org/people problems were very complex, and I learned a huge amount from it. I wouldn’t say I came to love Data Engineering, but I did come to love helping improve the organisation of a large x-functional team, and help fix team dysfunctions. I would not have learned anywhere near as much, nor as quickly, without this opportunity, and it served me incredibly well for the following 10 years.

On another occasion I took on responsibility for the CRM team and then the Performance Marketing team at Deliveroo.

How can I quantify this?  Overall, while not evenly distributed across the years, I estimate I was learning from a challenge quite far outside my comfort zone about once a year on average.  Each such challenge might last a few months or a year+, and of course there was plenty of smaller-scale learning overlapping all of that.  Many of these challenges were (like a job change) carefully chosen by me.  But quite a few were a result of the circumstances I found myself in, somewhat outside my control, and a willingness to say yes to hard new things that were critical to the company.

What other ingredients are needed?

As I mentioned briefly above, good and supportive leadership, mentorship and manager (not necessarily all 3) are typically essential to success in this.  And you want to be surrounded by good/great people, and amongst them (whether peers or leaders or team members) there should be at least a few super-stars from whom you know you’ll learn lots.  You don’t want to feel like you’re entirely alone tackling something new!

Next up will be “Lesson 5: superpowers”