The Small Words of Big Challenges

Do you need me?

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Around 2 minutes to read

The meeting was about to start, and Mike wasn’t there.

I went to his office to find him working at his desk.

“You coming to this meeting?” I inquired.

I was a newly minted associate design director at Big Spaceship, the least tenured of all the design directors. The agency was structured as collection of autonomous teams, and each team had a design director and a senior producer at the helm. I had just gotten promoted, which meant I now had my own team of 6, and I was working on my first account. Being new to the role, my manager—the CEO Mike Lebowitz—came to all my client meetings.

But he wasn’t in this one.

“You coming to this meeting?” I inquired.

“Why? Do you need me?” he responded.

“No…oooo?” I questioned, looking for any signal that this wasn’t the vote of confidence I hoped it was.

“Ok then.” He returned to his work.

No one has ever run a meeting more confidently that I did that day.

Running that meeting, running my team, and running multiple accounts gave me the self-assurance to eventually run my own agency after I left.

I met up with Brian Williams for lunch one day when he was visiting Philly. I was about 5 years into running SuperFriendly, and our revenue hovered somewhere in the mid-to-high 6-figures each year.

Brian asked, “Do you think the SuperFriendly model could scale?”

“I do.”

“Why don’t you?”

“Because I don’t really need to.”

“So?”

Huh. I had no counter for this two-letter challenge. Brian knew I was looking for the next challenge in my business. He knew I thought there was untapped potential that I never really tried to realize to date.

But he didn’t say any of that. He didn’t have to. All he said was, “So?”

Over the next few years, I experimented with different ways to scale an agency, from growing to a team of 65 to curating a network of 700 freelancers to bringing in 8-figures of revenue.

Sometimes the biggest challenges come from the smallest words.

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