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Issue #11: On Being a Leader


James Costa

May 9 · Issue #11 · View online

A batch of thoughts, resources, and motivation from a friendly digital agency owner delivered every Monday at 6am ET.

Taking the step back to be a leader is scary. For those of us running agencies, we mostly started them the same way: we were creating for fun or for a company, decided to take the plunge into freelance, and then things started snowballing. We’ve always been an intrinsic part of the DNA of our businesses, and find it hard letting others take over. While part of our fear of leading comes from not thinking that others could care as much about our businesses as we do, I think a larger part of this fear comes from thinking that there isn’t any value in being a leader.
I believe if we’re doing our jobs right and hiring the right people, we should be playing ourselves out of our job. It’s not to say that we’ll never have work, but our job will change. And that’s scary. Anyone who has had a major life change from work or personal knows that there’s a fear of the unknown that tends to drive a lot of people from leaving the jobs they hate. But overcoming that fear and taking the leap is incredibly important.
And after ignoring that fear for a brief second to take the leap into being a leader and empowering your people, guilt is likely to set in. Suddenly you have days where you feel that you have nothing to do and you feel like a slacker. You still get paid the same (or might have even taken a raise), but your to do list seems smaller than ever.
This past couple weeks, I honestly have been the least involved in my company than I have been in 7 years of running it. It’s not to say I haven’t done anything, but my team has stepped up in a big way to help me go through running a massive event, buying a house and moving into it, and preparing for marriage and all of the things that will be coming with it. And throughout the entire time they’ve not only been respectful of my time, but have been handling every problem that has come their way with the same care that an owner would. They’re not partners. They don’t have a share of profits (yet). But they have a profound sense of ownership that is inspiring.
I think that’s what being a good leader is about. It’s about building a team that have a common vision and care for everything they do, regardless of whether you’re there for every decision. That’s something that was the outcome of small actions over months and years, and teaching the team that they can make decisions without me, and that failing is okay as long as we learn from it. The decision to move into a more strategic role was one that was unanimously agreed across our team as being important. I never thought it would be, but I think people need a good leader.
A few weeks ago I wrote about what it meant to be an entrepreneur in tech, and how the term “entrepreneur” has become connected to ego and a profound sense of immortality (as long as someone else is footing the bill). In reflect on that issue, I think running a good business is consistent with being a good leader. Yes it’s great to continue growing your headcount and sales pipeline, but I think an even more important metric we should look at in businesses is how much ownership our team feels they have.
It’s okay to be a leader.
P.S.: I’m going to be taking a break from the newsletter for the next two weeks to get married, go on a honeymoon, and try and recover from a crazy couple months. I plan on getting things back to normal on May 30th for everyone. Thanks again for continuing to read and support. 😘
P.P.S.: If you have a moment and enjoyed this week’s issue, I’d really appreciate your support sharing this newsletter. Whether it’s a forward, a Twitter post, or etching my name into a piece of wood, it would mean the world to me.

Good Reads
On the dark art of software estimation
How we hire at Scrivito
Employee Onboarding is BROKEN
Is your company really only doing $45,000 per month?
The real reasons you procrastinate — and how to stop
Inspiration for the Week
A leader is best when people barely know he exists, when his work is done, his aim fulfilled, they will say: we did it ourselves.” - Lao Tzu
In Closing
I put out the garbage for the first time as a homeowner on Friday which was pretty exciting. That was, until the local raccoon(s) decided it was a good idea to ransack my organics bin. (Bastards.) I took my fury out on Twitter and have been getting daily messages from the local raccoon Twitter account. I’m glad you all love me enough to be able to laugh at my pain. 
If you have any questions or I can help you in any way, all you have to do is respond to this email.
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