This is the second in a three part series on the Operators Dilemma - you can read the first post The Operators Dilemma #1:Navigating your career through the Start, Build, and Scale journey.

• Navigating VC-backed Business Stages: Recognise the different stages of a company's journey—starting, building, scaling—and identify where your strengths and interests align.
• Self-awareness and Role Fit: Embrace introspection to understand your unique skills and where you fit best within a company's growth phase, ensuring both personal fulfilment and organisational success.
• Applying Ikigai Principles: Integrate the four components of Ikigai—what you love, what you're good at, what you can be paid for, and what the world needs—to find meaningful and rewarding work.

In the world of venture capital-backed businesses, finding your place can be a complex journey. The Japanese concept of Ikigai, often described as the intersection of what you love, what you are good at, what you can be paid for, and what the world needs, offers a useful framework for this exploration. 

Understanding where you ideal fit in the stages of a company's lifecycle—whether it’s the exhilarating chaos of starting up, the structured build phase, or the scaling for growth—requires deep self-awareness and introspection. By aligning your personal strengths and passions with the needs of your role, you can achieve a fulfilling and impactful career.

First you need to understand the realities of life in a VC backed business, the reasons for the short tenures, the reality of the different stages companies must go through to success: starting, building, scaling. Secondly you need to get in the mind of the founder. We covered these in the first post here.

Then you need to understand yourself, where you best fit into that journey which requires a level of introspection and self awareness that can bee challenging. Richard Freyman expresses this better than anyone: the first principle is you must not fool yourself, and you are the easiest person to fool. 

As Jennifer Bers explains, start by reflecting on the work and stage you love. 

After leaving Onfido, I really loved the idea of being part of a very early stage business, even earlier than Onfido which already had several million in ARR, and seeing the growth from the very beginning. It would have been a great story. The reality though, is that not only didn’t I love it, but I also wasn’t very good at it. That ‘start’ stage requires a different mindset. Not only did a layer (me) between the customer and the founder create almost a ‘telephone’ game which then necessitated more calls for the founder to dig in with the customer as product-market fit was still being researched, but my skills, value and interest just wasn’t needed. I realised that my sweet spot lies in taking organised chaos (the late stage of ‘build)’ and putting in a machine to help properly scale the business, and orchestrating the whole GTM function between themselves and the rest of the business.  Jennifer Bers, Notion GTM Advisor.

I really like the philosophy of Ikigai, which is one of those Japanese words which is almost untranslatable, but we can try. It has two characters. The first one – Iki (生き) - is life, or something that is alive. And the second character – Gai – (甲斐) -  means “worthwhile or something that has meaning.” Then if you put both things together it is “something that has life and is worthwhile.” In French it could be “la raison d’etre.” 

There are four components of Ikigai: what do I love to do, what am I good at, what am I paid to do and what the world needs.

So let's start with what you're good at. This can change a lot. We get used to being told as children we are good or bad at something. But as we mature we start to build skills in roles we play. Often this is shaped simply by the experiences we find ourselves in, and through repetition become really good, perhaps even excellent, at something.  We are what we repeatedly do. Excellence is a habit not an act. Aristotle.

But, just because we are excellent at something, does not mean we love it. When we think about the work we excel at, certain aspects come through strongly as the work that brings us real joy. The work we can lose ourselves in, the work in which we find ’flow.’

Now what you are paid to do is clearly important - at least to most of us - at very least as a recognition of your worth and to provide us with what you need to sustain the lifestyle we choose. Though research tells us it's not the most important factor. 

Far more important to many is self-actualisation and leading a life with meaning and purpose. Which brings us to the last point, i.e. what the world needs. Within the context of this discussion I am constraining this to the purpose that is fulfilled by helping a company (or a series of companies) to achieve their goals. After all, there is something incredibly powerful by being in a business that is forging a new path and bucking the odds of success.

So my simple premise is this - if you can combine these four factors - work you are good at, that you love to do, that you are paid well for, that serves a greater purpose - then as Confucius says, “you we will never work a day in your life.” 

So ask yourself this. Are you a starter, a builder or a scaler? What brings you the most joy?

Do you like taking companies from nothing to something, do you like bringing order to chaos, do you like optimising and fine tuning, do you like being an individual contributor, or a manager of ICs or a manager of managers. 

I think back on my time at MessageLabs, the last few months, and the sleepless nights and the anxiety I felt. It makes me shudder how naive I was and how little I understood about myself and what the business needed. On reflection while enjoy the start stage, and am comfortable with the ambiguity and the chaos, like Jennifer, where I find my joy is in creating order, developing models and frameworks to simplify and align a business. That was the work that brought me real satisfaction at MessageLabs, aligning the business around its very best customers, segments and markets. What I didn’t enjoy - and also am not very good - is managing a complex organisation, holding people to account, managing managers. So as MessageLabs motored through $50m revenue I found myself increasingly lost. Now I can look back and say the business made the right decision moving me on. They treated me well and I left fully vested. And more than ten years later I rejoined that very same team at Notion Capital and have had the time of my life.

Armed with a better understanding of the discontinuous nature of startups and of ourselves, you can start to ‘choose your own adventure,’ which is the subject of the third in this series, The Operators Dilemma # 3 - Mastering the Art of Career Development in VC backed startups.

If you are interested in learning more about the philosophy of Ikigai, you can revisit an interview we did a few years ago with Hector Garcia here and you can read Hector’s wonderful book here: Ikigai: The Japanese secret to a long and happy life.

A note from author of Ikigai

"I love seeing people advance the concept of Ikigai. I co-wrote the first book on Ikigai, but we only defined the foundations of the philosophy. Over the years, one of the most common questions we get asked is: How do I apply Ikigai in business, in the office, in startups, and in entrepreneurship? That’s why we need people like Stephen to provide us with the tools and a way of thinking about how to keep Ikigai present to guide us while building a business or working together with others towards a common goal while being connected with our purpose."