When You Come to a Fork in the Road, Take It

Zion National Park, Utah; photo by the author

About a month ago I told the Smartling team that I’m leaving the company at the end of this year. I plan to take some time off to recharge after having spent the better part of five years giving my job everything I have.

Smartling has just scratched the surface of its potential. The market for translation and localization is massive, and the company has a stellar customer roster and team, which means the best is yet to come. And, I can think of no one better than my friend and colleague Kunal Sarda to take over responsibility for leading its customer-facing team.

I’ve been humbled—and overwhelmed, to be honest—by the number of people on the team who have asked me for career advice since I announced my departure. Here’s my answer to the most common question I’ve been asked: “What can I do to advance my career?”

Many of my posts have touched on the importance of simplicity: The One Sentence / Paragraph / Page Framework, Four Great SaaS Visualizations, and Understanding “Closed Lost” are three examples. And more are coming: in the new year I plan to write about the importance of simplicity in pricing, incentive compensation plans, and product roadmaps.

As Dave Kellogg says: simplifiers go far, complexifiers get stuck.

If you’re given an opportunity to take on new responsibility, find a way to say yes — even if it’s uninteresting to you, if it feels overwhelming, or if you’re concerned that you might fail. Actually, say yes especially if you’re concerned that you might fail. I’ve found no better way to advance my career than to gain exposure to many different areas of a business, particularly the ones with which I had little or no prior experience.

Or, to quote one of my favorite baseball players: When you come to a fork in the road, take it.

A prerequisite is that you work for a company that will give you opportunities. I’m lucky to be batting 1.000 so far: both Atypon and Smartling gave me opportunities that I probably wouldn’t have been given elsewhere.

Actually, this isn’t exactly correct. The key is to work for a manager who will give you opportunities: someone who realizes your potential and makes it possible for you to work towards achieving it. For this I’m forever grateful to Georgios Papadopoulos, founder and CEO of Atypon, and Jack Welde, founder and CEO of Smartling.

While pursuing all of these opportunities, just remember not to lose sight of your work–life balance. I’ve made that mistake before (for my first five years at Atypon I was in the office at least six days a week—entirely by choice, I should make clear) and don’t care to repeat it.

Somewhere along the way you’re going to let someone down; get a promotion for which you weren’t the only candidate; displace one of your colleagues from his or her position; have to terminate an employee; or do something else that makes you unpopular. If you treat business like a popularity contest, you may find that results are suffering, or that you’re the one getting passed over for the promotion or displaced from your position.

To be clear, I’m not advocating for a self-above-all mentality. That’s a toxic mindset. And, business almost never is a zero-sum game: successful companies and teams find ways to expand the tent, rather than accept a culture of fighting for the limited space inside. Being selfless is an essential behavioral trait. As Sandler teaches, “You can’t have true rapport and trust until you say something that isn’t in your best interest.”

Still, your professional development will slow or stagnate if you constantly reign in your ambition out of fear of breaking a few eggs. Much of striking the right balance boils down to how you communicate and build trust. I’m guilty of having done things the wrong way on occasion—not because I cared only about myself, but because I was inexperienced and didn’t place enough emphasis on striking that right balance. I’m working on it.

Finally, it would be remiss of me not to recount the story of an exchange I had a number of years ago. An hour into a one-on-one conversation with a multi-billionaire, I asked how much of his success he attributed to luck. His response: “Ninety-nine percent luck and one percent super luck.”

This was a man with a true rags-to-riches story. It would have been easy and quite reasonable for him to say that while he had gotten lucky along the way, it was hard work and determination that created his success. His answer was telling, and it sent a clear message:

Be humble. Nobody achieves success alone.

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Chief Customer Officer at Brightflag. I write about issues relevant to and situations faced by SaaS companies as they scale.