28 Lessons from 10 Years as a Social Entrepreneur
This is the second episode of my “Back to the Ranks” series of transitioning from social entrepreneur to senior management. In the first episode, I discussed how you know when to step down: Knowing When to Walk Away.
Something I’m Learning
This entry began as a series of short LinkedIn snippets I posted over a few months last year. Now here they are all collected in one place.
On (Social) Entrepreneurship
1. Expect it to be hard. The world will resist your attempt to change it. That’s why you shouldn’t become an entrepreneur unless you can’t sleep if you don’t give it a go. It’s not a joy-ride and it’s definitely not glamorous, despite pop culture’s valorization of a few success stories.
2. Be a user yourself. Design a product you would use yourself. It will make you constantly aware of what needs to be kept and what needs to be changed, and also help you believe in it passionately yourself. Indeed, for many entrepreneurs, when you would no longer be a user of your own product, that’s when you know it’s time to exit.
3. As you grow, yes becomes no. Entrepreneurship or starting up is about saying yes to most things because you don’t know where they might lead; management or scaling up is about saying no to most things because you need to focus on the most critical. It's a culture change that isn't easy to navigate.
4. Don’t go it alone. Whenever possible, have a co-founder. Choosing to reject several mentors’ advice and have a co-founder was the best decision I’ve ever made, not just for the organization but also for my life.
On the Co-Founder Relationship
5. Equalize equity and risk/skin in the game. Make sure you both put in comparable amounts of equity, sweat equity and risk. I’ve seen a lot of founders offer someone the “co-founder” title without an equal co-investment, and it almost never turns out well.
6. Build unshakeable trust. You have to believe in your co-founder’s values and intentions. There will be times you bitterly fight, and others when you fundamentally disagree, but if you trust their intentions, it becomes a lot easier to resolve conflict and accept their decisions. This is hard to do and takes a lot of time, but the benefits are immense.
On Hiring and Managing People
7. Recruitment feels like rocket science. Hiring is the hardest thing to get right. In other words, it’s where you will make the most mistakes. Looking back on the last 10 years, perhaps 80% of the things I’d do differently relate to hiring choices rather than programmatic or strategic or financial choices.
8. Choices indicate values. When hiring, purpose-fit is more important than culture-fit (put another way, purpose-fit is culture-fit). Look for occasions when people have made life choices that indicate alignment with the organization’s mission. It is a much bigger predictor of long-term success in the role than most things on their CV or in interviews.
9. Recruit for different experiences than your own. This is obvious for mature organizations but even for start-ups, it’s extremely valuable to bring in early teammates from sectors and backgrounds different to yours. They will bring new ideas for products/programs and new markets that you hadn’t previously considered, and that could provide all sorts of new opportunities.
10. Feedback is a polarity or Catch-22. Feedback often tells you more about the giver than the receiver (in the way that your choice of role model says more about you than about them i.e. it’s usually all projection). And yet it’s essential to provide feedback often and well. Walking that tightrope is a core management skill – there are few true masters and everyone can always do it better.
11. Don’t “fire fast”. I’ve never gelled with the management mantra of “hiring slow and firing fast”. With the exception of ethical violations, don’t be too quick to fire people. Give them time and multiple opportunities to bring their strengths to bear, and to learn from their mistakes (if honestly made).
12. You are not your role. Nobody else in the organization sees more of the elephant than you do. So they will misunderstand and draw incomplete/false conclusions about you, many of which will hurt. Even as you aim to improve your communication style, provide more timely feedback, and be self-aware, some acceptance that being misunderstood is inevitable will save you much heartache.
On Managing and Investing in Yourself
13. Learning vs performing mode. One of the best mental hacks to de-stress yourself in high-stakes situations (like a big public speech or a major funding pitch) is to view it as an opportunity to learn rather than a stage on which to shine. It also makes it easier to stomach failure and re-frame it as feedback.
14. Ignore the medium-term. Keeping the lights on matters (duh!), and the long-term goal matters. The medium-term is not a useful timeframe to think about because it’s both too close and too far away to be useful.[i] Forget about “where you see yourself in 5 years” and don’t ask anyone else that either, especially not in interviews. Spend most of your time accomplishing short-term goals that have long-term value, but also play long-term games that have little short-term value.
15. Reclaim “judgment” for the white hats. A few years ago, it was common to hear people being called “judgmental”; yet, that never resonated as an epithet. Good judgment is a rare skill. Prize and reward your teammates who demonstrate it. That said, hold your opinions loosely because everything can change as you get more data and the broader environment evolves.
16. Reframe mentorship. Someone doesn’t need to know they are your mentor (often it’s actually better for your relationship if you don’t put that title on them). Also, your mentor can be a fictional character. It’s what you learn from their example, not what they tell you to do.
17. Try new things in non-work arenas. Experiment with what you eat, read and watch; how you exercise and do your hair; your choices around friends, money, and hobbies. Personal experiments lead to new insights and opportunities just as often as professional ones do.
18. Prioritize your long-term health. I had a major a-ha moment when I was told that the choices you make in your 30s will determine your quality of life in your 50s. As an entrepreneur, I never skimped on sleep, but I wish I had learned the importance of eating healthy much, much earlier.
19. Most boundaries you face are in your own head. Mental models can be shifted, especially your own.
On Personal Growth and Fulfillment
20. It’s also inner-preneurship. Starting an organization is an opportunity to learn more about yourself: to discover your potential and your limits, what you truly care about and what you do not (some of which will surprise you). Whether you fail or succeed, you will be changed by your work, if you have to have the courage to face what needs to change in you.
21. Connecting success to happiness. The outcome of doing good work is the opportunity to do more good work. Your happiness is directly related to whether, depending on your state of mind, you replace the word “outcome” in the previous sentence with either “prize” or “price.
22. Embrace the Stretch Zone. The best indicator of personal growth – and a source of great fulfillment – is noticing that something that was a stretch for you has now moved into your comfort zone.[ii] It’s also how you know it’s time for your next stretch.
23. Appreciate the hard times. When you look back on your entrepreneurial venture (or your career as a whole), the things you will be most proud of are not when you were in cruise control. You will be nostalgic for the tough times, the feeling of slogging up a mountain. Only then are the views worth it.
24. Being vs Doing. In the professional realm, your inner life, values, and emotions only matter in the context of how they manifest externally. People often draw a false dichotomy between “being” and doing”, similar to the one between “work” and “life”. Being and doing should inform each other in a constant dance, like breathing in and breathing out.
25. Know when to walk away. While perseverance, grit and relentlessness are super skills that distinguish the best entrepreneurs from the rest, there is also wisdom in knowing when to quit, when the current situation is no longer the best match for you and there are better possibilities available.
Other Unconnected Lessons
26. Seek out your peeps. Having a community of practice is the antidote to feeling weird or crazy compared to your family, classmates and the friends you grew up with who can’t comprehend your life choices. This is partly why there are so many ‘fellowships’ in the social impact industry. Find the groups who don’t think you’re crazy for your life choices – and participate actively in those communities. The returns – both practical and psychic – are immeasurable.
27. Work out loud. All these posts have come from my 10-year global journey as a social entrepreneur. I’ve tried to share insights throughout, most often in essays for the Stanford Social Innovation Review. This helped me crystallize what I was learning as well as contribute back to the sector, to hopefully help those who come after. Indeed, this whole newsletter project is another attempt at keeping that flow going.
28. Distrust absolutes. Few things are always true. As Aaron Sorkin writes in The West Wing, things with absolute rights and wrongs usually involve body counts. Nearly everything depends on context and things change over time and across a career (and life). So whenever someone – a funder, teammate, boss, pundit – presents something as immutable fact, then tread carefully, as in the parable of the Zen farmer. Therefore, please contextualize or adapt anything in here that works for you, and discard the rest.
Something to Consider
Speaking of a social entrepreneurship journey, if I ever have the money, I’d love to fund something like this: From debt to diversity: A journey of rewilding, carbon capture and hope.
Something to Quote
Studying entrepreneurship without doing it is like studying the appreciation of music without listening to it. Until you confront the fear and discomfort of being in the world and saying, "here, I made this," it's impossible to understand anything at all about what it means to be a entrepreneur. Or an artist.
[i] This is one of the lessons of the Three Horizons framework, which is just as applicable personally as in business.
This is great Roshan. Very helpful to me and I think for others as well.
Really enjoyed these reflections, most of them resonate a lot! Great curation 🙂