When it comes to growing your career, there’s long been a thriving debate over the merits of building generalist vs specialist skill sets. Spoiler: there is no right answer. In reality, whether to build a generalist or specialist skill set (and therefore career path) relates much more to two things: What do you enjoy? What […]
Talent-Company Fit is the Career Equivalent to Product-Market Fit
What do the people with the most fulfilling career trajectories have in common? The most obvious trend: top performers act like owners. Performance leads to leverage. Leverage creates career opportunity. It’s common advice. In order to make the biggest impact on your company, treat it like it’s your own. See a problem? Solve it. Have […]
Five Techniques for Chasing Your Unanswered Callings [Research Summary]
In Every Good Endeavor, Timothy Keller introduces the book by referencing back to Robert Bellah’s Habits of the Heart, starting with a passage on the perils of individualism at the expense of all else: “We are moving to an ever greater validation of the sacredness of the individual person, [but] our capacity to imagine a social fabric that […]
What are you optimizing for? (Or, why I want more moments of joy)
I get in bed and pull the covers up around me. I roll over to tell my wife good night. She’s already fast asleep and cuddling our younger dog like it’s our child. I take a moment to simply watch them sleep peacefully before turning the light out. We invite ourselves over to our close […]
Am I Enough?
When things are going well, it’s easy to wait on the other shoe to drop. “See, I knew I wasn’t doing enough,” I expect to say some day in the future when it all falls apart. I don’t have what it takes. I’m a fraud. When things are going poorly, it’s easy to ride the […]
Define Your Flywheel to Fuel Faster Business Growth
In his classic management book, Good to Great, Jim Collins shares an idea called a flywheel. That concept can help you and your company define what drives growth and then do more of those things over time. It’s a powerful tool for strategic clarity. Collins recently expanded on the concept in a recent manifesto called […]
A Simple System for Creating Community Based on Dunbar’s Number
My wife was busy on that Saturday afternoon in 2014, so I pulled out my list of my friends in Atlanta and sent a flurry of texts inviting 10-15 of them to grab dinner with me in Virginia Highland. Five or six of them said yes and we ended up grabbing wings and beer at […]
How to Plan a Team Retreat for Your Remote Company
19% of remote workers say that loneliness is their #1 struggle with working remotely according to Buffer and company’s 2019 State of Remote Work report. I can relate. While there are so many strategic advantages to running a remote team, there are also some parts of working remotely that really suck from a personal standpoint. […]
How to Recover from a Mistake as a Leader
March 1, 2018. I won’t forget that date any time soon because it was the day I made my first major mistake as COO… and it had taken less than 6 hours in the role to happen. “We can’t keep letting this happen. We just lost one of our largest customers to a completely avoidable […]
How We Structure the 50-Person Team at ConvertKit
As a team grows from the early stages when everything feels fun and crazy into a more mature phase of predictable growth, team structure has to change to support that growth. When I joined the ConvertKit team in 2016, we had about 20 teammates and $3.5M in annual recurring revenue. Today we have almost 50 […]