Ten Years of Lessons

Kiva Dickinson
7 min readOct 18, 2021


Lately I’ve been reflecting on the time I spend helping younger people navigate their careers. This has always been a passion of mine, but recently for a number of reasons I find myself not seeking it out the same way. Part of it is that I feel like I’m less helpful the more removed I am from the tactical decisions these people are making. Recruiting for investment banking internships and private equity associate jobs is honestly so different than it was back when I did it — I honestly don’t think the way I navigated the path would work today. That said, I think the bigger reason is that I’ve grown more reflective and philosophical as I’ve gotten older, begun to build a family and taken the entrepreneurial leap. Frankly, most college students who reach out are trying to get help finding a job, not looking for my musings on the meaning of career, life and risk.

The reason that I originally got so immersed in mentoring college students and young professionals is that ten years ago my path into investing did not start smoothly. As a junior in college I applied to all 20 investment banking job postings and didn’t land an interview at a single one. It was only the kindness of the many alumni that I cold emailed that got me on track to landing an internship at Barclays. For years the only way to make sense of my good fortune was to pay it forward: give hours of mock interviews, respond to every cold email, volunteer to run recruiting at my firms and take young people with good hearts and more talent than me under my wing. Very unintentionally I do much less of that now.

Rather than dive back in and give outdated, out of touch tactical advice I want to help more young people find their passion and path faster than I did. That means sharing some of the lessons I’ve learned along the way, including the ones I’ve learned the hard way. I’ll start with ten really powerful lessons that have stuck with me in the first ten years of my career. I hope these reflections can help someone as much as they have helped me.

1. Don’t kick the can on specialization

Early on I thought the key to career-planning was to accumulate optionality. ”Do investment banking because you can do anything afterwards”. “Avoid a narrow industry group so you’re not pigeon-holed”. “You can always decide what you want to do later, just make sure you’re qualified for it when you figure that out”. Implicit in that thinking was the premise that one day the clouds would part and my calling would emerge. In hindsight that was so passive. The truth is most people who accumulate optionality aren’t moving closer to discovering their passion; in fact, they’re actually letting their eventual peers compound knowledge and network that they will one day wish they had. Don’t be afraid of trying something you’re interested in — it’s so easy to pivot industries in your twenties and early thirties. It gets harder as you get older.

2. Pave a unique path

When I used to look up at leaders I admired I would often study the path they took to reach their role. I would do so to reverse engineer their success: presumably following paths of precedent was the way to land coveted roles. I can’t say that’s never true: partners at many law firms and private equity firms would easily disprove that thesis; but I can say that uniqueness is undervalued in that thinking. Following precedent paths, no matter how prestigious or credentialed, inherently makes you a commodity (even if a scarce and expensive one). Holding experience that nobody else has makes you invaluable to the right role, and irreplaceable once you’re in it.

3. Learn finance & accounting

If I could change one thing about undergrad business programs it would be the culture of finance. Never has there been a less diverse, collaborative and inclusive field of study. I now have so many friends and contacts who are incredibly smart and personable who don’t have more than a very basic grasp of accounting and finance because they were not attracted to that culture in college. That’s a real shame because finance is the language, scoreboard and fuel of business. Economics is how the world works, and what dictates the outcome of the vast majority of government elections. A good understanding of both practical and theoretical finance can be your “Trojan horse” to be in a lot of really interesting conversations and decisions. Starting out in Investment banking is not the only way, but it is a great place to start *especially* if you don’t want to stay but just don’t know what’s next.

4. Start writing publicly sooner

I wish I had started writing publicly earlier. I remember starting drafts and editing over and over, never quite feeling like something was ready to publish. Eventually I learned that not enough people read your early content for you to get real negative feedback — the goal is not perfection it’s volume (so long as there is baseline thoughtfulness). Sure it helps to build a brand, but more importantly it makes you a better strategist and communicator. There are a handful of folks who are polite enough not to say they told me so (but they definitely did): Matt Ball, Mike Dempsey, Ryan Caldbeck to name a few. Writing publicly is the advice that I most commonly give to others that is so rarely followed.

5. Prestige vs responsibility

A couple of years out of college I was talking to a close mentor who had finished his MBA a year before. He told me something that always stuck with me: “of the people I graduated with, a year later the happiest ones solved for responsibility at the expense of prestige, and the unhappiest did the exact opposite”. I honestly didn’t understand it but now I very much do. Rarely can you have both prestige and responsibility early in your career, in fact I’ve found them to be quite inversely correlated. It takes confidence to forgo prestige but it can be so worthwhile when you do.

6. Risky vs scary

Jim Koch had a powerful insight when he left Boston Consulting Group to found the Boston Beer Company. While it appeared risky to leave a comfortable and coveted job to launch a beer brand, it actually wasn’t risky at all — it was just incredibly scary. In fact, the riskiest (and least scary) thing he could do was stay at BCG: passively remaining in a job that he knew he would never be happy in long-term. More clearly defining risk and what it really means when discussing personal life decisions has been an incredibly useful learning process for me. I never would have started a business without unpacking and quantifying the risks to my finances, career prospects and self-esteem if it failed.

7. Cold email

Sending cold emails has probably yielded the most asymmetric upside of anything I have done in my career. It directly led to my first job out of college, two of my most successful investments and over 5% of the attendees at my wedding. It has never (to my knowledge) caused me a single ounce of harm. It is the perfect example of something scary with effectively zero risk.

8. Zoom out

Zooming out means two things to me: first, when things are tough zooming out will give me the perspective I need to mentally battle through. I often visualize how stock market volatility can look so intense in a 5-day view and then appear to be effectively a straight line over 5 years. Careers are the same way: as I write this I can’t even remember things that prevented me from sleeping 6 months ago. At the same time, when things are good, zoom out and be long-term greedy. Being younger has the advantage of more time to compound the value of relationships. Play the long game: keep planting seeds and watering them — don’t be tempted to reap the harvest too early.

9. Be easy to root for

No matter how talented, hardworking and credentialed you may be, the most powerful inflection points in your life can be created by somebody choosing to believe in you and taking interest in your success. That might be a boss, a professor, a mentor or an investor. They will root for you not only because they see your potential but because they like you and want you to reach it. Never waste that opportunity by being difficult to root for. Humility, curiosity and sincerity are so attractive to mentors, and yet so often people blow it by trying to appear more successful or knowledgeable than they already are (usually to impress their listener). Knowing who you are and being yourself will be a magnet for good people into your corner.

10. Your mentors are people too

When I was in college and started getting serious about networking I was frankly in awe of my mentors. I looked up to them absolutely; they appeared to have everything I wanted and were so sure about everything. As I’ve gotten older I’ve realized by getting to know them better (and in some cases stepping into the roles they held when I met them) that they have fears and worries just like I do. They may not want to confide in their college mentee, but that does not mean they don’t crave human connection. Simple things like asking about their family, wishing them happy birthday, learning about their interests and remembering those things for next time will fundamentally change your relationship with these people. It sounds obvious, but mentors and mentees can become friends, and when that happens it’s awesome. That may never be in the cards for a certain relationship, but they only way to find out is to remember that they are people just like you.



Kiva Dickinson

Consumer Investor / Founder of Selva Ventures / Proud Canadian Living in San Francisco