2025 annual reflection and my plans for 2026

2025 Reflections

After reflection, the annual themes that summarize 2025 are:

  • React

  • Survive

  • Postpone

A family crisis dominated 2025. After an unexpected event, we took over parenting of our niece (Reece, 15) and nephew (Porter, 21). We assumed responsibility for their finances and got them settled, which put a lot of stress on our family, but we stepped up in a big way, and I’m proud of us. Along the way, I learned far more than I ever wanted to about family law and how to gain guardianship through the courts, yet we navigated the system and got what we needed. This was incredibly hard and quickly became the year's top priority, which meant other goals had to take a back seat. I’m very proud of Sable and my efforts here, and even prouder of how well Reece and Porter have responded.

Personally, a few things are going well. I’ve made real progress on weight loss, dropping about 20 pounds. I’ve been consistently reading fiction at night and falling asleep without sleep aids. And I’ve started writing every day again. At the same time, I’m missing some key pieces: I did far less nonfiction reading this year, I’m not publishing my writing as regularly as I’d like, and I still want to build much deeper technical knowledge in AI.

Family-wise, our kids are developing nicely and are a joy to be around—Avery has started chattering and talking in full sentences, Oliver did soccer and ski lessons, and learned how to swim, and I loved driving my niece to school and skiing with her on the weekends. Our new home in Utah has been a real blessing. I’m home for dinner most days, and I’ve enjoyed regularly cooking for the family on my grill and smoker. The highlight of the year was our beach trip to Charleston, which was an awesome family vacation together. Though I didn’t get back to North Carolina to visit my extended family as often as I’d have liked.

At LegUp Health, some things went well in 2025. JD is now at his monthly target compensation, and we hit the $20K MRR milestone mid-year. At the same time, the expiration of Obamacare subsidies created massive uncertainty, and we lost long-time consumer and employer clients as a result.

At Windfall, 2025 was a transformative year. The company raised a $65M Series B, which was a win for investors, for my friends who founded it, and for employees. I’m learning a ton and still making meaningful contributions across the business. At the same time, I’m still very much “in the weeds” and have failed to scale myself (one of my 2025 goals) amid the AI chaos in revenue operations. On the one hand, AI represents a massive opportunity for leverage; on the other, it’s hard to determine which use cases are legitimate and which are hypothetical.

2026 Planning

The annual themes that will drive 2026 for me are:

  • Getting back to basics

  • Going from reactive to proactive (and surviving to thriving)

  • Shifting from a strategy of playing it safe and reducing risk to taking smart risk and being ok looking a little foolish

2026 Personal Goals:

I’ve listed out my personal goals below in a checklist format.

  • Get back to basics in daily personal life

    • Continue weight loss journey and Ski/Bike/Play Bball when I can (target 185 lbs)

    • Daily writing/exercise

    • Up at 5 am, bed by 9 pm

  • Getting back to basics in the family operation

    • Adjust the family budget to meet our current needs

      • Simplify meal planning with pre-planning and explore ways to seek help from family, services, etc.

    • Protect time and space for Sable and me to prioritize our personal health, professional aspirations, and passions

  • Be proactive in supporting the kids’ advancement

    • Help Oliver develop skills in his interests (sports, swimming, skiing, playing, etc.)

    • Regular 1:1 time with Avery doing stuff outside the house

    • Help Reece get into a college she is excited about + take her skiing on the weekends

    • Help Porter transition to living as an independent adult

  • Be proactive about spending time with people I care about

    • Create regular quality time with Sable 1:1, and protect it

    • Take Sable/kids on 2 really awesome family trips

    • Support and be present in Sable’s 10-year sabbatical at Lucid

    • See my Lindquist extended family every quarter (ie, every few months, even if it means I go back solo)

    • Spend time with LegUp Health Partners more intentionally (potentially revisit the monthly cadence/format)

    • Support Julian Castelli with his efforts in his Growth Elevated community

2026 Professional Goals:

I’ve listed out my professional goals below in a checklist format.

  • Outsource, delegate, or automate recurring tasks that I no longer value doing and/or others don’t value me doing

    • This is a more specific, actionable way of saying, "scale myself.”

  • Try to grow LegUp Health by 50%, but do it in a way that excites the partners.

    • Now that we are “default alive” with JD’s target base salary covered by MRR, we have fewer constraints and can start to explore creative paths for our next big bets.

  • Upgrade personal website to a better website structure, and get back to consistent content production + read 10 really, really good nonfiction books and publish notes on them

    • Ship new content, daily while going deeper on fewer topics with reading and writing (vs trying to cover it all).

    • Areas of interest include:

      • Data Science and Statistics (as they related to AI)

      • Increasing chances for good luck / decreases changes from bad luck

      • Human psychology as it relates to decision making

      • Local networking / community / connection / building relationships

      • Improved parenting

  • Experiment with AI to generate 1 additional revenue stream

    • I figure this will be a fun way to force deeper learning and hands on experience with AI tooling in 2026.

Inspiring Quotes for 2026

“A personal metric: how much of the day is spent doing things out of obligation rather than out of interest?”—Naval

“If someone watched you for a week, would they believe you’re serious about your goals?”—Unknown

“My hunger is not for success, it is for excellence. When you attain excellence, success naturally follows.”—Coach Mike Krzyzewski

"The output of clear thinking has never been higher in human history. The output of being busy has never been lower in human history."—George Mack

“Go at it boldly, and you'll find unexpected forces closing round you and coming to your aid.”—Basil King

Questions to Ponder for 2026

  • If you weren't allowed to complain about this thing anymore, what action would you have to take?

  • What is this teaching me?

  • What can I delete/remove?

  • Are your goals big enough?

  • Am I avoiding what I want for fear of being disliked?

  • What am I scared of failing on? And how can I get ok with failing at it faster vs trying to prepare for it?

  • How can I find meaning in my current suffering?

  • How can I create luck for myself?

  • When things go well for others, do you enjoy cheering them on or do you hate to hear about their success?

  • When things go wrong, do you believe it is your responsibility to improve the situation or do you blame others?

  • Which activities, if doubled (or halved), would make your life meaningfully better?

Reading, Writing, Publishing Goals for 2026

13 books to read and take notes on:

  • How to Lie with Statistics

  • Naked Statistics

  • Math Without Numbers

  • Data Science for Business

  • How Not to Be Wrong

  • Storytelling with Data

  • Talk to strangers

  • The Psychology of Money

  • The Snowball

  • The 48 Laws of Power

  • Influence: The Psychology of Persuasion

  • Success and Luck

  • Competing Against Luck

  • The Intelligent Investor

13 notes to revisit update:

8 handbooks to publish and progress

Have thoughts on this topic? I'd love to hear from you on X or LinkedIn.

Reflections, PersonalRick Lindquist