The Founder’s Paradox

The Founder’s Paradox: The Shame of Failing at Mindfulness

Founders Paradox Mindfulness

The thrill of achievement is irresistible. It is gratifying to set a goal, work hard to accomplish it, and then start to look forward to what is next. Thinking beyond today is part of achieving and yet we are often shamed for not being “in the moment.” The paradox between mindfulness and ambition can be disconcerting. This is especially true if you are someone who enjoys constantly striving. You know the best version of you is still coming.

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The Founder’s Paradox: How to Make Clear Decisions When the Future Is So Cloudy

I never imagined that I would talk with our company about a pandemic. But for many leaders, last week brought the unimaginable. It did for me on Wednesday, which I typically set aside for deep introspection and strategy. I spent that afternoon going through my own assumptions about the potential impact of coronavirus on the world, our company, our customers, and our team. Those reflections were the basis for a heartfelt conversation with the entire Aha! team last Friday.

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The Founder’s Paradox: How to Make Difficult Work Desirable

difficult work

Difficult work gets a bad rap. Tough to scope, complex to explain, and hard to deliver — I am sure you can think of some projects that would fit this description. When you are deep in it, the effort to break through can be tortuous. But I would wager that these projects are also some of the most impactful too. Either because of what you achieved or what you learned.

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The Founder’s Paradox: The “Future You” Might Not Like the Choices “Today You” Is Making

founders paradox future you

The guy with the laptop. This is how I am known by one of my kid’s soccer coaches. Let me explain. The kids need to be there 45 minutes before games to warm up. There is not much for parents to do during that time except chat with each other. So I pull out my laptop, find some shade, and work. Once the game begins, I put the laptop away to be fully present for the game. This is a conscious choice. But I do miss out on those pre-kickoff conversations with other parents.

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The Founder’s Paradox: How Do You Grow Really Fast Without Losing Your Soul

grow fast startup culture

It was our third Aha! onsite. Twice a year our entire remote team gets together in a destination location. This onsite was in Park City, Utah. After a week of meaningful sessions, many great meals, and even some bobsledding, everyone lingered to chat on the final night. As I looked at the talented folks on the team who were excited to be doing something different and great together, I could not help but feel a bit wistful.

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The Founder’s Paradox: How to Know When to Change Course and When To Keep Going

Founder's Paradox: Change Course

I love the adventure of travel. I am always looking to see and learn something new about a place and the people who live there. Right now, I am writing this from Italy where I am vacationing with my family. Driving here has been an adventure itself. The streets are ancient — narrow, wildly winding, and punctuated by faded signage that confuses more than guides. There have been quite a few “Are we sure this is the right way?” conversations with my wife and kids.

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The Founder’s Paradox: How to Work on Vacation and Still Have Fun

founder's paradox: work vacation

The idea of a “vacation” has always somewhat bothered me. Not because I do not like to travel. (I love exploring new places. I am actually writing this post while in the San Diego airport.) And not because I do not think people deserve a break. We all need time to focus on other obligations and hobbies. Mostly because the way we talk about vacations infers that you need to escape your regular occupation — completely.

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The Founder’s Paradox: How to Balance Certainty With Uncertainty

Founder's Paradox: Uncertainty

We are living in uncertain times. You could say this has always been true — life is unpredictable and so are we. People are complex. And as much as technology has brought us closer together, it has also drawn in stark contrast all the ways that we are different. Social media, in particular, has been used to amplify those differences. There is confusion and chaos, conflict and turmoil. It can be hard to project calm strength when uncertainty rules the day.

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The Founder’s Paradox: How to Stay Focused When Other Opportunities Keep Tempting You

founder's paradox opportunity

It takes courage to have a single focus. I have been thinking about this a lot lately. Because while it takes chutzpah to set really ambitious goals, that is not where the bravery comes in. No, that comes later, when you have to recommit over and over to the vision you have set in order to realize it. This kind of focus is not always easy — especially in rapidly-growing companies where there are so many promising new opportunities to pursue.

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The Founder’s Paradox: How to Know What Decisions to Make and What Should Be Left for Others

founder's paradox decisions

We make decisions all the time. Some are small, subtle, you could even say reflexive — grab a coat in case of rain, scoop up the kids’ backpacks rather than waiting for them to do it themselves. (Getting them to make that choice would require years of coaxing.) There are of course more middling everyday choices, like what to eat for dinner. (Ad infinitum.) But what about at work, where even your subtlest decisions can impact so many? Read more…