Thinking of A Career Change?

Making a career change can be scary, and difficult. So many considerations on career trajectory, growth, pay, level, title, etc. etc. Especially when it feels like your'e really ramping up on your current trajectory.

However, I fundamentally believe that as humans, we are multi-faceted beings and I think it is more likely than not that we will explore different careers during our working lifetime especially if you lean towards generalist on the generalist - specialist spectrum.

In my ten year career so far, I've spent a third of that as a management consultant, turned operator scaling multinational tech startups like Uber, and, and more recently I have transitioned into Venture Capital as an early stage investor. I want to share five mental models that have helped me in my journey and I hope that it helps someone out there who perhaps is considering a career pivot.

Define The Trigger

I’ve always been an advocate of a proactive approach to your career and I often know what the purpose of every role is in my personal development and growth plan. Because of this, I know when I have hit my goals for any role I am occupying at the time and when I need to set new ones. You see – I had a singular goal when I transitioned from a management consultant to an operator at early stage startups - - learn how to scale multinational startups.

I spent four years scaling Uber, and in leadership roles, building teams across departments, raising funding and essentially building and scaling a startup without being a founder to millions ($) in revenue. After evaluating my progress, I realized I was close to achieving the goals I set for the role.

So, the question was what next? What do you want to learn, and why? And it was on this basis I started my exploration of potential next steps in my journey.

Gather The Data

I started considering a career pivot a year before I actually made the jump and at this stage, there were quite a few unknowns. I’m a planner by nature but in retrospect, an iterative approach served me immensely. I had gathered operating experience, I wanted to know what my options were. So I went on a fact finding expedition.

I researched potential career options for folks with operating experience. A few options came up. Product Management for a Global Product, Venture Capital, and of course, becoming a founder myself as I had built the skills and network to do so. I found Venture Capital fascinating, but equally thought starting a venture of my own would be too. When you find something naturally exciting, I believe it could be a signal. Dig deeper. It could mean something, or not.

So, I started my research, and that was when I stumbled on Elizabeth Yin's amazing early stage investor blog. I reached out to her and she kindly responded, and asked a million questions. I chatted with my VC friends at the time who were just starting out their funds, and who are at existing funds. They were generous with their time and honest responses and helped me get an existing player’s perspective.

Run Experiments

I still believe we learn by doing, at least I do, and this was the purpose of the MBA in my journey. It gave me the space to run experiments to validate the hypothesis of what I enjoyed doing in the long term.

Co-incidentally i read Designing Your Life, a book that helped me even better iterate through this process. With the experiment, i was to discover;

  1. What naturally energized me, and i what found exciting

  2. What naturally drained my energy, and i found difficult to sustain/maintain

  3. What i’m relatively better with less effort (what comes naturally to me compared with others)

  4. What i struggled with even with a lot of effort compared to others

  5. What existing skill sets i had that were valuable in the context of a new career (my edge)

The aim was to answer those questions and essentially shape what I wanted to do – to find something that aligned with the strengths and skills I had built, and used less of the weaknesses I had. But I had to first put myself in these positions over an extended period to really know. So, During the MBA, I built an app (managing developers) and went through the exciting process of ideating an app idea, building a PRD, recruiting and managing developers to build a functioning product. It felt a little like managing a product (i think). It didn’t matter to me if the idea went on to be successful or not (it was not successful), I learned so much during the process.

During this time, I also kicked off my investing journey by doing. I led the Oxford Seed Fund as the Managing Director investing in Oxford-Affiliated Startups, and I spent some time with the amazing Hustle Fund team as an MBA Intern, reviewing hundreds of deals a month and learning from an incredibly experienced, talented and kind team who were willing to give me direct feedback that gave me critical information i needed to make a decision. I also made several investments that have now gone on to perform incredibly well in such a short time – we wait and see what the next decade brings on that front.

I learnt so much about myself during that period and answered all four questions above.

Make an Informed Decision

Now I had the data, and I also had a strong and informed rationale for my move and could adequately assess the trade-offs that might be required. The beautiful thing is it felt more natural because it was iterative – like several little steps as opposed to one giant leap. Of the three options above, I chose Venture Capital.

It is risky to make a career decision without setting a goal. At least for me, they were two sides to a coin. Remember my earlier comment about being deliberate on the purpose of a role in my journey? Although it's hard to predict what your journey is like prospectively, planning never hurts. It gives milestones that force retrospective reflection and act as guardrails. You can be on a very fast train going to where you no longer want to go, and to me, that’s dangerous.

It’s been almost two years of being an investor and I cannot believe the amount of growth that has happened in that period. It’s mind blowing. I believe it is directly correlated to the amount of learning that has had to happen.

I hope these mental models help you as you think about your journey. Making a career pivot is scary, but I think that they are an amazing way to grow horizontally, which sometimes is much more rewarding and impactful in the long term.

Till next time 👋🏾




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