Back of Mind

The Best Career Advice I’ve Ever Gotten

Though I didn’t know it at the time, a partner at Bain Consulting gave my 24 year old self what is still the best piece of career advice I’ve ever received: change your role, or change industries, but never both. The underlying logic is that new roles and new industries have steep learning curves, and you’re better off climbing one learning curve at a time, while leaning on competence in the other to be a contributing and valued member of a team. I got this advice on my way out of Bain, after my search for an operational role at a cleantech startup didn’t bring the opportunities I had hoped. The companies I applied to recognized what I did not, that I had neither the operational experience nor the cleantech expertise to deliver enough immediate value.

After the wisdom of this advice took to heart, I joined Village Ventures, where I could immediately take advantage of the business skills I had learned at Bain, while being thrown into the deep end of this new and unfamiliar startup ecosystem. I had comically little understanding of the VC-startup dynamic, the various flavors of startup wisdom that I now take as given, and perhaps most importantly no knowledge of, or certainly connections to, the influential thinkers and doers in the NYC startup world. However, what I could do was quickly and competently boil down the dynamics of a business or market, prepare a professional and compelling presentation, and chew through and make sense of mountains of data and information. While I was a startup baby, I relied on these abilities to make a place for myself on the Village Ventures team.

Through four years at Village Ventures, and with the generous mentorship of so many, Bo Peabody and Matt Harris particularly, I was able to move from a baby to an adolescent in my knowledge of the startup ecosystem and dynamics, and perhaps even young adulthood in a few markets, digital media and advertising technology particularly. With whatever startup and industry acumen I’ve been able to develop, I found myself with a far more exciting opportunity than the operational roles I had lunged for at 24 when I was lucky enough to join SimpleReach as President.

Again the same dynamic played out, though in reverse of Village, in which I struggled mightily, and continue to struggle, up the learning curve of my new role, while using my knowledge of digital media and venture capital to immediately contribute to the team. As SimpleReach CEO Eddie Kim will attest, I wasn’t much of a salesman when I joined, but I quickly added to the strategic, market, and fundraising thinking.

I’m cognizant of the way in which this highly practical and seemingly conservative advice contradicts the ‘you can do anything’, ‘find your passion’ ethos we often rightly celebrate in the startup ecosystem. However, I’ve found that by tackling steep learning curves one at a time, you maximize the value of your past experience and knowledge while placing yourself well outside your comfort level and forcing yourself to learn and adapt. This approach also keeps you from the grass-is-greener phenomenon we are all vulnerable to, in which ignorance of a job or industry makes it seem more attractive than it truly is. You can only be so uninformed about roles in your industry or functional area.

This approach marries two core, shared human dynamics: we want our efforts to have meaning, and we learn best when pushed to the limit. By combining our strengths and weaknesses in new opportunities, we balance the need to learn with the need to matter. And there’s nothing contradictory about that.

16 Factors To Consider In Choosing A Cofounder, From Hunter Walk →

• Timing re availability and when to start the company
• Working with any life circumstances (geography, significant other, etc)
• Who is CEO
• How hard to work
• Skills maturity alignment
• Alignment on what core competency you want to build a company around
• Complementary on optimism v.s. paranoia tendency
• Complementary on details v.s. big picture focus
• Preferences on enterprise v.s. consumer
• Aiming for big swing v.s. base hit
• Having basic functions covered: hiring, marketing, product design, eng, finance, management, etc
• Able to communicate well (similar mental primitives, compatible styles of disagreeing)
• Similar levels of commitment to the startup
• Able to share burdens / support each others’ psychologies and stress levels
• Anything else that goes into trust
• Anything else that goes into how you feel about being in the room with the other person for 12 hours a day

Desiderata

Go placidly amidst the noise and haste, and remember what peace there may be in silence. As far as possible without surrender be on good terms with all persons. Speak your truth quietly and clearly; and listen to others, even the dull and the ignorant; they too have their story.

Avoid loud and aggressive persons, they are vexatious to the spirit. If you compare yourself with others, you may become vain and bitter; for always there will be greater and lesser persons than yourself.

Enjoy your achievements as well as your plans. Keep interested in your own career, however humble; it is a real possession in the changing fortunes of time.

Exercise caution in your business affairs; for the world is full of trickery. But let this not blind you to what virtue there is; many persons strive for high ideals; and everywhere life is full of heroism.

Be yourself. Especially, do not feign affection. Neither be cynical about love; for in the face of all aridity and disenchantment it is as perennial as the grass.

Take kindly the counsel of the years, gracefully surrendering the things of youth. Nurture strength of spirit to shield you in sudden misfortune. But do not distress yourself with dark imaginings. Many fears are born of fatigue and loneliness.

Beyond a wholesome discipline, be gentle with yourself. You are a child of the universe, no less than the trees and the stars; you have a right to be here.

And whether or not it is clear to you, no doubt the universe is unfolding as it should. Therefore be at peace with God, whatever you conceive Him to be, and whatever your labors and aspirations, in the noisy confusion of life keep peace with your soul. With all its shams, drudgery, and broken dreams, it is still a beautiful world. Be cheerful.

Strive to be happy.

http://en.wikipedia.org/wiki/Desiderata

How I Learned To Love The Rain

As a kid, I hated the rain. We humans are terrible at reconstructing why we thought or felt anything, but my best recollection is that I hated the way it dirtied my world. I hated the way all that water would pick up grime and dust and flotsam and spread it to my floors and shoes and the bottoms of my pants. Through childhood and adolescence, I’d scowl at the ugly dark grey storm icon on Pittsburgh’s KDKA six o’clock news, fearing each day that the rain would steal the fun from my childhood love, anything involving a baseball.

That all changed one day in the Spring of 2000. That day I found a mental secret weapon that has helped me since more times than I can count. I’m a high school Junior driving through a hilly suburb, the kind of place where there are large undeveloped stretches of grass, maintained by unseen municipal workers, or neighborhood groups, or one thoughtful citizen, I never knew or asked. I’m halfway home when the sky opens up. On comes one of those Spring rains that my Oldsmobile Bravada windshield wipers had no chance against. One of those rains that makes you wonder how so much water could ever have been held in the sky. So over I pull into an undeveloped stretch of grass to wait out the worst of the storm inside my water-tight, plastic-clean, air-conditioned box.

After a minute or two, out of nowhere, comes an urge to be out in the midst of all that rain. There was something so primal about the ferocity of the deluge; I suddenly wanted to be in it. So out of the car I step, phone and wallet left behind, not quite trusting this odd instinct. Within 30 seconds I’m drenched to the bone, and it’s…GLORIOUS! Drops rolling down my face, I turn it upwards, opening my mouth like a child catching snowflakes. I spun, and lept, and yelled…and that hated rain turned to joy. When I came to, fingers pruned, I got back into the car and slowly pulled out of the grass.

Thinking of this odd behavior over the next days and weeks, when I wasn’t paranoid a high-school classmate had seen me (as one does about any out-of-the-norm behavior in HS), I realized that all of those scowls, all of that dread, were not from the rain, they were from me. And I had the power to change them. 

All these years later I still catch myself scowling at rain clouds, and I still dislike dirty floors, but then I remind myself that I can choose to love the rain, turn my face to the sky, and open my mouth.

What’s your rain?