Emotional Investors' Update #1 (2023-02-13)

Hi! You look amazing today and I’m so grateful for you.

What is this?

The following is the first of what I hope to be many monthly letters to you and other “emotional investors” in my life. The idea being that, like an investor update, sent to keep those that have invested monetarily in the outcome of a business, this would be a similar update for those that have had some emotional investment in my past, present, or future. An attempt to keep them up to date with everything they need to know about the latest goings ons (because we all know how much I love talking on the phone). I’m hoping this will be fun and something people are open to. I’m also (selfishly) hoping to use this as a way to regularly write more for clarity and growth.

My hope is that after reading this, you might reply and fill me in on what’s going on with you or give you a chance to ask any follow-up questions. I’m going to try to do this at least once a month, so if you want to keep getting these updates, you can sign up here.

Hope this all makes sense. Now… on to the updates…

TLDR:

• Work: my team at Able.com recently released our new web-based tool to help freelancers, contractors, and other 1099 workers not get caught off guard with surprise tax bills.

• Life: bought a house in Chicago last April, my son is growing like crazy, and getting to spend this time with him is amazing.

• Productivity: been slowly working on re-organizing my tools and processes for managing my life and building in my free time again. It is going well so far, I think.

• Upcoming travel: Seattle in February, Ireland in April.

• Sponsors: Able.com, Weekofthewebsite.com, Fathom Analytics

For those that want more details…

Work:

For the last 2 years+, I’ve been working as engineering lead for Able.com, which focuses on trying to help make it super easy for freelancers, contractors, or any other 1099 workers to manage their finances and not deal with a surprise tax bill when it’s time to pay taxes. We’ve done an amazing job of building but not a great job of marketing and getting out in front of those that might benefit from our tools. This past month, we finally release a highly requested web-based tool to complement our mobile apps, along with a paid subscription offering for those that find it useful. Really proud of what we’ve been able to build, so fingers crossed that we can find product-market fit with our target audience.

Life:

For those that aren’t familiar, we are almost a year in our new house in Chicago and still loving it. Grateful every day for us to have a place for our son to grow up that is so accessible to tons of the amazing things this wonderful city had to offer like parks, music classes, museums, family, and tons more we haven’t even had a chance to take advantage of yet. He’s about to turn 17 months and doing amazing. Growing like crazy and smart as a whip. His newfound vocabulary is a game changer, and we definitely need to start being more careful about what we say in front of him, as he’s quick to mimic. But we are also still working on handling the frustrations around not being able to communicate all the things he wants. All the new teeth coming in aren’t helping with the irritability. As I’m sure you’re aware, life is very hard for a baby. But he’s got a good support system (including amazing loving grandparents that love babysitting), so I’m sure he’ll get through it.

Productivity:

The hardest part of the last 2 years for me (I won’t speak for my wife) has been adjusting to our life’s new evolution. Before our son, it wasn’t uncommon for us to be working a majority of our time as we tackled ambitious work during the days and then transitioned into working nights on side projects and extracurriculars. But once he came, we quickly learned that was a thing of the past. He and my wife became my top priorities, with a close second being maintaining a stable income to help us continue enjoying our beautiful lives.

In the last couple of months (since about November), after we mostly got caught back up on sleep, my creativity and desire to work on new projects have slowly come back. But it’s been difficult to adjust to my new priorities and limited availability. To help with this, I’ve started to explore how I can adjust how I work to better fit into my new life. I’m calling the project Rebuild and it’s been an opportunity for me to chronicle my investigations into more efficient ways for me to work and prioritize my own creative endeavors.

As part of this, I’ve taken part in a program called “Building an Intentional Life” by Sean Johnson (a Kellogg professor and a prominent part of the Chicago investment community). During his 6 week program, in addition to having a cohort of other successful professionals looking to optimize their lives, the main tenants of the program revolve around establishing your values and 10-year goals and helping build out the tools to help you reach those goals. It’s been incredibly encouraging while also being extremely challenging, but I’m really enjoying it and the friendships I’m building. I’m currently down a rabbit hole of building my personal operating system in Notion (affiliate link). Once I finish setting it all up, I’ll do some sort of walk thru talking about what I’ve done and why I think it’s helpful. But for now, I’m really enjoying the clarity this is helping bring to my process and I’m looking forward to jumping into my next project once I wrap with this program.

Upcoming Travel:

The family and I are flying to Seattle this week to spend some time with friends from Portland whom we haven’t seen in years. They have a son a little older than ours whom we’ve never met. We are renting a house on an island, bookended with overnights in Seattle.

In April, we are going to Ireland with some family. We will spend some time in Dublin but mostly down country in Kilkenny, Waterford, and Wicklow. Excited to spend time exploring the beautiful countryside and spending time with family.

That’s it for now. Hopefully, this is interesting to you and you’d like to continue hearing these updates. If so, feel free to subscribe, but if not, I won’t take it personally.

Sponsors:

Fathom Analytics - an amazing privacy-focused analytics tool from my friend and former cofounder, Paul Jarvis.

WeekoftheWebsite.com - my brilliant and beautiful wife’s company, which helps creatives build a beautiful and easy-to-maintain website in just one week (or two if you’re doing something really fancy).

Able.com - my current employer, which helps freelancers, contractors, and other 1099 workers not get caught off guard with surprise tax bills.

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