I took a year off.

Writing that feels weird, almost like confessing to a crime. After I left Fundera/Nerdwallet at the beginning of this year, I committed to taking 6-9 months of time with one rule: I couldn't make any decisions about what to do next. I had never taken an extended break before - I had always known what I was going to do next and let momentum carry me from one place to another. It generally has served me well, but I wanted to try something new in the hopes that a break would allow me to reset and give me more clarity and confidence.

Taking time off is most certainly a privilege. I did all the cliche things one does: travel, spend time with family, read, exercise, pickup old hobbies, spend time with friends, etc. All of that was absolutely wonderful. It was also genuinely shocking and borderline frightening how fast days would go by. But the downtime can also be extremely difficult. All I've known is forward motion and planning for what comes next, so this was unfamiliar territory (although, perhaps committing to clearing my head and making no decisions was preparing for what comes next).

I learned a lot about myself over the past year. I found that so much of my identity was tied up in what I did. Telling people "I'm taking a year off" was a really strange thing to do. It made me question who I was. My whole professional career I identified as a tech entrepreneur, and all of a sudden I was in between things.

I went deep on a series of ideas that could have easily turned into startups. One was around programmatically enabling any company to build a world-class SEO program, another was a "roll-up" of internet businesses that had indestructible product market fit around people's various passions, and another was on preventing heart disease (which I will publish some more thoughts on soon because I'd really like to help someone accomplish this). I came within inches of starting one of them, but it was within my "No Decisions" window and I'm glad I stuck to it. The easiest thing for me to do would have been to start another company. It's all I've really known, and it's the thing that I most identified with. Not starting something during this period was very difficult.

I did my best to go with the flow and embrace the idea of wu wei to see where it would take me. I'm very happy with the process and thrilled with where my journey concluded. Next month I'll be tackling something new for me with a group of people I've long admired and respected. I'm equal parts thrilled and nervous. It's an evolution of what I've been doing, and I am eager to step outside of my comfort zone and embark on a new adventure. I don't think this opportunity would have emerged had I not sat still for a bit. After ample time off exploring, I feel like I have boundless energy to deploy. I'm ready to go.

Reflecting on the experience, these are some of my most important takeaways:

• Hobbies bring great joy. I rekindled my love with tennis, joined a club, and hit 1-2 days per week. I'm playing at a 4.5-5.0 level with ex-D1 players and I love being competitive again.

• The world is big and beautiful and should be explored in a variety of different ways if you can. Traveling to new places by myself, with family, or with friends was wonderful. I'm committed to adventure.

• There's nothing better than quality time with family. I got a lot of it over the past several years and had the opportunity to watch my kids grow.

• While working from home had its benefits, I am very over it. I need to be in an office with people making things happen. There's no substitute for it for me. People have different styles. Mine is in person. I also find that being in the office during the day makes me more present when I am home.

• It's easy to mentally atrophy if the break is too long. I recommend time off to anyone who can do it. But 12 months is too long for me. Somewhere between 3-6 likely would have done the trick.

I entered this hiatus with a great deal of uncertainty. And while there's more clarity about some things, there are still countless unknowns. I'm looking forward to continuing to explore them, whatever they may bring.

One of the worst feelings in the world is having a sick child. Nothing eats at your heart and soul more than the feeling of helplessness that is watching your kid feel ill. Like all parents, I’ve had plenty of harrowing experiences with my children ranging from hospital stays with viral meningitis to a one year old turning into a blue balloon with serum sickness. Nothing makes me more sad and anxious than seeing one of my kid come down with a bug.

Another unfortunate thing about kids being sick is having to physically go to a doctor's office for just about everything. Some pediatricians do some form of telemedicine, many through Klara in my experience, but they'll seldom diagnose or prescribe anything without seeing the child in person. At first I thought it was understandable, but so many of these diagnoses are rather rote and can be done with a photo or video. The other downside of having to physically go into your pediatrician is that you can never see them when you want, which is always as close to Now as possible. The options are normally wait a couple days or make your way to urgent care. More often than not what a parent wants is to simply know that things are fine and that tylenol/ibuprofen are good for now.

Last year I learned of a service called Summer Health that enables you to text with a pediatrician 24/7. The communication is pretty much synchronous and I love it because it nearly instantly provides me peace of mind. Every time I text Summer I'm sent a link where I can view the credentials of the pediatrician I am speaking with, and I enter a real-time SMS conversation with them within minutes. I've talked to them at all hours of the day about things ranging from head bumps, questions about strep throat, how to remove excess silver nitrate on one of my kid's faces from a procedure at an ENT, whether you can administer antibiotics if they're expired but have lived in the refrigerator, what medications are okay to take with norovirus, how to know if your child is a carrier for strep, and many more things from the mundane to quite serious. They also call in prescriptions and frequently ask for photos or video to better understand a condition. All of my interactions have been pleasant. And while the doctors don't always nail the condition (eg maybe they think something is croup instead of another respiratory issue), I get an educated opinion quickly and know whether I can wait a day to take my kid in or if I should get a move on things. The service is roughly $20 per month which is an easy price for me to stomach paying for the peace of mind I get from it.

Watching Novak Djokovic play tennis is a pure delight, but I love listening to him talk about tennis even more. He's the GOAT - a perfectly tuned machine with a deeply intrinsic sophistication when it comes to the game. I always look forward to watching his post-game commentary. He has become an exemplar of sportsmanship, remarkably gracious when he wins and loses.

Earlier this week he played an incredible match against Jannik Sinner where he lost in three sets. You can watch the highlights here (they're incredible). What stood out to me more was Djoker's analysis of the game. Listen to how he talks about it, remembering every critical point and juncture throughout the match, reciting specifically what happened and when.

My favorite part is how he attributes Sinner's win to the fact that he was "more decisive and courageous in the moments he needed to be." He also notes, "In these types of matches very few opportunities are presented and if you don't use them the other player will."

So much about these comments remind me of company building. When I talk to entrepreneurs and look back on my own journey, so much of the story and outcome is usually attributed to having the courage to be decisive in the most important moments, which are almost always filled with ambiguity at best and more often absolute existential chaos. It's incredibly frightening to step up in those moments - it's much easier to let them pass you by. But having the courage to make decisions during these defining times, whether they are right or wrong, is oftentimes the thing that makes or breaks a company. It's one of the most important hallmarks of entrepreneurship.

I took a year off.

Writing that feels weird, almost like confessing to a crime. After I left Fundera/Nerdwallet at the beginning of this year, I committed to taking 6-9 months of time with one rule: I couldn't make any decisions about what to do next. I had never taken an extended break before - I had always known what I was going to do next and let momentum carry me from one place to another. It generally has served me well, but I wanted to try something new in the hopes that a break would allow me to reset and give me more clarity and confidence.

Taking time off is most certainly a privilege. I did all the cliche things one does: travel, spend time with family, read, exercise, pickup old hobbies, spend time with friends, etc. All of that was absolutely wonderful. It was also genuinely shocking and borderline frightening how fast days would go by. But the downtime can also be extremely difficult. All I've known is forward motion and planning for what comes next, so this was unfamiliar territory (although, perhaps committing to clearing my head and making no decisions was preparing for what comes next).

I learned a lot about myself over the past year. I found that so much of my identity was tied up in what I did. Telling people "I'm taking a year off" was a really strange thing to do. It made me question who I was. My whole professional career I identified as a tech entrepreneur, and all of a sudden I was in between things.

I went deep on a series of ideas that could have easily turned into startups. One was around programmatically enabling any company to build a world-class SEO program, another was a "roll-up" of internet businesses that had indestructible product market fit around people's various passions, and another was on preventing heart disease (which I will publish some more thoughts on soon because I'd really like to help someone accomplish this). I came within inches of starting one of them, but it was within my "No Decisions" window and I'm glad I stuck to it. The easiest thing for me to do would have been to start another company. It's all I've really known, and it's the thing that I most identified with. Not starting something during this period was very difficult.

I did my best to go with the flow and embrace the idea of wu wei to see where it would take me. I'm very happy with the process and thrilled with where my journey concluded. Next month I'll be tackling something new for me with a group of people I've long admired and respected. I'm equal parts thrilled and nervous. It's an evolution of what I've been doing, and I am eager to step outside of my comfort zone and embark on a new adventure. I don't think this opportunity would have emerged had I not sat still for a bit. After ample time off exploring, I feel like I have boundless energy to deploy. I'm ready to go.

Reflecting on the experience, these are some of my most important takeaways:

• Hobbies bring great joy. I rekindled my love with tennis, joined a club, and hit 1-2 days per week. I'm playing at a 4.5-5.0 level with ex-D1 players and I love being competitive again.

• The world is big and beautiful and should be explored in a variety of different ways if you can. Traveling to new places by myself, with family, or with friends was wonderful. I'm committed to adventure.

• There's nothing better than quality time with family. I got a lot of it over the past several years and had the opportunity to watch my kids grow.

• While working from home had its benefits, I am very over it. I need to be in an office with people making things happen. There's no substitute for it for me. People have different styles. Mine is in person. I also find that being in the office during the day makes me more present when I am home.

• It's easy to mentally atrophy if the break is too long. I recommend time off to anyone who can do it. But 12 months is too long for me. Somewhere between 3-6 likely would have done the trick.

I entered this hiatus with a great deal of uncertainty. And while there's more clarity about some things, there are still countless unknowns. I'm looking forward to continuing to explore them, whatever they may bring.

One of the worst feelings in the world is having a sick child. Nothing eats at your heart and soul more than the feeling of helplessness that is watching your kid feel ill. Like all parents, I’ve had plenty of harrowing experiences with my children ranging from hospital stays with viral meningitis to a one year old turning into a blue balloon with serum sickness. Nothing makes me more sad and anxious than seeing one of my kid come down with a bug.

Another unfortunate thing about kids being sick is having to physically go to a doctor's office for just about everything. Some pediatricians do some form of telemedicine, many through Klara in my experience, but they'll seldom diagnose or prescribe anything without seeing the child in person. At first I thought it was understandable, but so many of these diagnoses are rather rote and can be done with a photo or video. The other downside of having to physically go into your pediatrician is that you can never see them when you want, which is always as close to Now as possible. The options are normally wait a couple days or make your way to urgent care. More often than not what a parent wants is to simply know that things are fine and that tylenol/ibuprofen are good for now.

Last year I learned of a service called Summer Health that enables you to text with a pediatrician 24/7. The communication is pretty much synchronous and I love it because it nearly instantly provides me peace of mind. Every time I text Summer I'm sent a link where I can view the credentials of the pediatrician I am speaking with, and I enter a real-time SMS conversation with them within minutes. I've talked to them at all hours of the day about things ranging from head bumps, questions about strep throat, how to remove excess silver nitrate on one of my kid's faces from a procedure at an ENT, whether you can administer antibiotics if they're expired but have lived in the refrigerator, what medications are okay to take with norovirus, how to know if your child is a carrier for strep, and many more things from the mundane to quite serious. They also call in prescriptions and frequently ask for photos or video to better understand a condition. All of my interactions have been pleasant. And while the doctors don't always nail the condition (eg maybe they think something is croup instead of another respiratory issue), I get an educated opinion quickly and know whether I can wait a day to take my kid in or if I should get a move on things. The service is roughly $20 per month which is an easy price for me to stomach paying for the peace of mind I get from it.

Watching Novak Djokovic play tennis is a pure delight, but I love listening to him talk about tennis even more. He's the GOAT - a perfectly tuned machine with a deeply intrinsic sophistication when it comes to the game. I always look forward to watching his post-game commentary. He has become an exemplar of sportsmanship, remarkably gracious when he wins and loses.

Earlier this week he played an incredible match against Jannik Sinner where he lost in three sets. You can watch the highlights here (they're incredible). What stood out to me more was Djoker's analysis of the game. Listen to how he talks about it, remembering every critical point and juncture throughout the match, reciting specifically what happened and when.

My favorite part is how he attributes Sinner's win to the fact that he was "more decisive and courageous in the moments he needed to be." He also notes, "In these types of matches very few opportunities are presented and if you don't use them the other player will."

So much about these comments remind me of company building. When I talk to entrepreneurs and look back on my own journey, so much of the story and outcome is usually attributed to having the courage to be decisive in the most important moments, which are almost always filled with ambiguity at best and more often absolute existential chaos. It's incredibly frightening to step up in those moments - it's much easier to let them pass you by. But having the courage to make decisions during these defining times, whether they are right or wrong, is oftentimes the thing that makes or breaks a company. It's one of the most important hallmarks of entrepreneurship.