How you know it’s time to move on… Lessons in leaving a job you love ❤

9 min readAug 5, 2021

Three weeks ago, I waved farewell to both the Connect team and the portfolio of founders. To say it was a hard decision to make is an understatement, but I have no doubt that it was absolutely the right decision for me.

Knowing the right time to move on from a role or a team you love is always going to be tough, so I thought I’d share some insights on how I navigated these waters including questions I asked myself and the loose process I followed which ultimately made it easier to reach and embrace my decision to leave.

A look back…

I joined Connect just over four and half years ago to build out the Founder Network (aka their portfolio community aka Platform). For those who aren’t familiar, Connect is a pan-European, seed stage, thesis-led VC which backs opinionated products, crafted with love and loved by many. Connect is the ideal home for any founder who is obsessed with solving user problems through software, while creating a delightful user experience in the process (check out these posts for more info: learn more about the thesis, how it’s used to guide investments, and how IC decisions are made).

I still remember the day the job spec landed in my inbox, courtesy of AngelList. The role sounded like my dream job; the chance to build something from scratch, taking on a role that hadn’t existed in the mainstream VC ecosystem for more than 5 years, and the opportunity to work with, support and serve a range of founders across the portfolio was everything I could have wanted. As a bonus, the fact that it was a time-boxed role i.e. a 2-year tour of duty, suited me to a T. I have always held the belief that 2 years is typically what it takes to know a role inside and out and do at least 80% of it with your eyes closed, and once you reach that stage it’s usually a good time to consider a new challenge — be it within or outside of the company. At Connect, I ended up staying twice as long as both the partners and I had initially intended. During that time I created some real impact for our portfolio, built wonderful relationships with founders and function leads, and learned so much in the process (more on this below).However the sad reality is, nothing lasts forever.

So how do you know when it’s time to leave, especially when it’s a place that made you? To answer this question, I had to go back to the beginning and remind myself of…

What I wanted to achieve in the role and how it worked towards my personal goals, and
How the role aligned with my personal values

Goals and achievements…

Although I knew very little about the workings of VC, by the time I joined Connect I had already spent four years working in / advising early stage startups, which gave me a foundational understanding of how these unique beasts work and the challenges they typically face. This allowed me to bring a level of empathy to my role which helped inform some of the first decisions I took around what we could offer our founders. Supporting these startups on their journey from Seed to Series A and beyond was literally my idea of living the dream and I was excited to take on the challenge.

When I accepted the role, I took the opportunity to crystallise the loose 10-year goals I’d set for myself in my previous end-of-year personal life review. In short, by the end of 2027, I would have successfully founded my own company armed with knowledge of how European, US & African startup ecosystems worked. In the immediate term, my primary goal was to use my 2-year term at Connect to learn the ins and outs of the seed stage ecosystem and gain some pattern recognition around the startups, which I could then use to inform what type of support we could offer our founders that was not only relevant, but also scalable and productised. The desired outcome was to design an offering that genuinely added value to the founders within our portfolio, and later to their function leads as well.

By the end of my first 18 months, the foundations were in place: I’d identified which areas the founders and portfolio were benefiting the most from, the types of support that were having the most impact, and which formats were the most popular. I had ideated and launched v1 of our Founders Retreat, which became a core part of our founder well-being offering / coaching support programme.

For more on that, take a look at this article I wrote about how we started the Network offering at Connect, why we conceived the Founders Retreat which was the first of its kind, and other general insights from the Platform community. Stay tuned for a follow-up post about how to build out Brand & People functions in a VC i.e. how to go from zero to one.

Personal values; asking the tough questions… and being brutally honest with yourself

Anyone who knows me knows that I’m a big fan of articulating your personal values and using this to guide your decisions and actions — both big and small. Two of my values in particular were key to my thought process in my decision to move on: Continuous Learning & Mastery, and Creativity. I’ll share another post shortly about how I chose my top five values (of which these are just two), and why they were key in my decision!

I hadn’t really thought much about what the next step looked like post-Connect , as I’d envisaged a promotion to COO which I’d been working towards and discussing with the partners. The COO role would essentially involve overseeing the individuals (or teams) leading on Platform, Brand & Culture Ops.

When other Tier 1 funds first started reaching out to me looking to grow or build out their platform function, I was certainly flattered and it was a huge sense of validation to have been recommended to these funds by other badasses in the ecosystem (the identity of some still remain unknown to me). While most of these conversations were interesting and I had a tonne of respect for the funds, it didn’t quite seem like the right fit. It did however force me to start thinking more about my future at Connect alongside my initial 10-year plan and personal values.

So, I worked on a diary and energy audit of:

how I was spending my time;
how did this align with my superpowers / where I get my energy from;
what this would look like in the COO role; and
how well this aligned with my likes, aspirations and the overall needs of the firm

Just as I was wrapping up this thinking, conversations began with two funds, one of which was in my top 5 wish list! These conversations were immediately more impactful as I was armed with a real awareness of what I wanted my next role to look like and how I wanted to spend my time. Long story short, one of the roles sounded exactly like what I was looking for next. It had enough similarities to my previous role — meaning that a lot of my skills would easily be transferable — and it offered the opportunity for a new level of complexity, especially around the investment stages and geographies covered by the new fund. I spoke with my mentors, family and closest friends to get their take, and ultimately, the right decision for me was also the hardest thing to do.

The fear is real… but necessary

Once I was sure of my decision and had communicated this to my team (still one of the toughest conversations I’ve ever had), “The Fear” set in… As excited as I was, I still felt:

the fear of leaving behind the safety and comfort of the team I’ve come to know (and love), and that had come to know me too
the fear that the team would be upset with me for leaving and that the relationships I’d spent years building would go up in smoke
the fear of leaving behind the legacy I’d spent almost half a decade building
the fear of having to build up credibility again — could I achieve the same (or even better) results again?
the fear of getting to grips with a different culture, a new, larger team, etc.

The good news is that I was expecting this, so I felt prepared. My notice period gave me 3 months to design the ultimate “exit experience” for myself and my team.

I definitely had ups and downs, moments waking up in cold sweats wondering if I was making a huge mistake. I spoke to peers who had made the move to other funds. I worked through specific fears with my coach, therapist, and family, and came up with a clear plan for my exit.

It definitely wasn’t easy but I’m glad to have gone through it now! While I still have a teeny bit of nerves in the background, I’m fizzing about the new role. As my father always said to me as a child: “feel the fear & do it anyway!”

Before I go… thank you

I’m forever grateful to team Connect, specifically Sitar, Pietro, Rory (& Bill), for taking a chance on me and giving me the opportunity to contribute to the awesomeness that is Connect in a meaningful way!

To the founders of the 40+ companies I was able to onboard and support during my tenure: Thank you for being open and willing to serve as guinea pigs while I tested, iterated and found “product founder fit.”

Looking back, I’m proud of what I was able to achieve, and the legacy I’m leaving behind! Highlights include:

Building the Connect Platform from scratch and learning to bring a product mindset to it
Creating the first Well-being & Leadership Founders Retreat in the VC ecosystem (check out this short video reel from our last one)
Putting founder well-being (and generally Connect’s well-being) on the map in a real way, long before it was cool (not to mention winning the Mindful Investor Awards two years in a row, in the process)!
Injecting some DEI thinking and support into our network offerings and helping founders build out their minimum viable activities from the outset
Building a robust online offering both (thanks to Notion, Airtable & Affinity) to make the tools and resources self-serve both internally, and to reach our founders far and wide
Building our first ecosystem newsletter, Connect the Dots. It’s awesome if I do say so myself, so sign up!
Kickstarting our first product newsletter — still an experiment but a fun one to work on!
Contributing to the development of our internal team by creating structure, processes and the general core company foundations
Becoming Chair of the EU VC Platform community
Becoming Vice President of the Global VC Platform community

(*NB: these two appointments were only possible off the back of the work done in my day job!)

Excited to see some of the ideas that I kickstarted flourish — I won’t share too much but a couple of them include…

Building out a product programme to further support our founders on all things product — fundamentals, resources, and know-how
Introducing cross-fund initiatives — partnering with funds with a similar- sized portfolio to increase the quality of interactions especially for the function leads at companies in our respective portfolios
Looking at our fund operations through a DEI lens — including the investment process, internal team activities and portfolio reporting

Questions to ask yourself when you’re thinking about moving on?

So if you’re currently thinking through your next adventure and what road to take, have a look at the checklist below for inspiration!

Why do you want to move to the next thing? Be specific.
What’s missing for you now that’s urging you to move on?
What are your short/mid/long-term goals?
Is your current environment still the place to help you achieve these?
When is the right time to move on i.e within the next 3–6 months or longer?
Do you feel like you’ve created the impact you wanted? If not, how far out are you?
How do you say goodbye to your legacy, team, and start fresh?
What’s the worst that could happen?

If you can answer these questions clearly and confidently, the path ahead should be clear — and hopefully easier to follow. And if you’ve recently been through a role change, I’d love to hear how you navigated this and the questions you worked through.

Answering these questions is what helped me determine the best path forward, and I hope they can help others in the same place too. Thanks for the memories, and see you very soon, Connect friends!