10 Questions to Ask Yourself Before 2026

I've done this every year since 2015. Here's why it's the most valuable thing I do all year.

👋 Hey, it’s Andrew.

I want to start by saying how grateful I am for you. Thank you… for reading these emails, for showing up to our events, for trusting me with your time. Being in your inbox is a privilege I take seriously.

This is my last article of the year. I hope 2025 was significant for you - and that 2026 is even better.

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It’s hard to believe 2025 will be over in less than a week.

It feels like yesterday when I was doing the same annual reflection exercise, but for 2025.

The theory of time compression states that your perception of time exponentially speeds up as you age, so that at thirty, a year passes 7 times faster than it did when you were five.

One way to slow down your perception of time is to hit pause, look back, and reflect whenever you get the chance. The end of the year is always a nice moment to do that.

For the last 10 years, I’ve always done a personal annual review. It’s been a pretty life-changing exercise to help me identify patterns and make better decisions.

The process is simple and quick. Here’s what I’ve realized: most reflection processes take HOURS, and that’s too much for most people. But this one is simple. 10 questions. 5-10 mins each. Totally doable in one sitting.

How to use this:

Don’t just read these questions and move on - that’s pointless.

Block 2 hours on your calendar, go somewhere quiet, and put your phone in airplane mode. Maybe your Spotify Wrapped will jog your memory?

Then answer each question, but not in your head. Make sure to write it down.

I do this every year between Christmas and New Year’s. It’s become one of my most valuable rituals. Some questions will be harder than others. Have fun with it.

Here are the 10 questions that may change your life.

1. What were your most meaningful moments?

Write out ALL the significant moments from this year - the good, the bad, the ugly. This serves as your starting point for everything else to come. If you do it right, you should have anywhere from 5 to 20 moments to reflect on.

If it helps, look through your photo album, calendar or journal. I find it helpful to list out moments in these categories: Personal, Work, Health, Relationships & Personal Finance.

I actually keep a rolling list throughout the year - something my first mentor taught me. When something happens, I write it down immediately.

For me:

• Taking my family on vacation to Portugal

• Speaking in front of 600+ people in Greece

• Visiting home in Hong Kong after a decade abroad to say goodbye to my grandmother

My keynote on the power of community building in Athens, Greece

2. What are you proud of?

If you’re anything like me, you immediately move on to the next thing after hitting a big goal. Stop doing that. Instead, acknowledge it, pat yourself on the back. You deserve it.

As a classic, type A ‘achievement’ chaser, I’ve gone down this path many times and learned that life starts to feel pointless if you’re just collecting wins.

Instead, slow down to reflect on it, and WRITE DOWN the things you were most proud of this year.

I’m proud that all our employees stayed throughout the entire year, no matter how hard it was. Half our team has been with us since the start two years ago, and the other half has been with us for over a year. They’re excellent at what they do and have options, and I’m grateful they chose to stay with us.

Our Fibe team at the end of 2025. Our team: Jacob (Partnerships), Danielle (Events), Sangavi (Marketing), Maks (Operations), and Vitoria, Anna, Anya, and Akash (Fellows). Also featured: Bailey, CEO of Cal.com - our friend at Fibe!

3. What were the biggest challenges you faced?

What was hard this year? These are the things that kept you up at night. And it’s totally okay if you haven’t solved them yet.

The point isn’t to dwell, but to understand - and be honest - about the thorns in your life right now. I’m also a big believer that if you hold a problem long enough in your head, your subconscious will eventually come up with solutions.

For me, it was dealing with shiny object syndrome. It’s hard to stick with building something like events when literally everyone around you is building AI and asking you when you will too. But I stuck with it - and now I’m more bullish than ever.

4. Which of your strengths has best served you?

I’ve learned that most people assume they’re average at everything, but that’s not true.

Over the course of my decade-long career, EVERYONE I’ve worked with excels at at least one skill - or has a unique combination of 2-3 skills they’re really good at.

It wasn’t until I left Google that I realized my biggest strength was ‘organizing chaos.’ No matter how complex a problem was, I could put a structure in place to help my team solve the problem. Even in the complexity of startup land.

5. What did you avoid because of fear?

Sometimes fear disguises itself as ‘being realistic’ or ‘waiting for the right time’. Your ego will seldom admit that you’re scared.

This question forces you to be honest about what you didn’t do and why. Write it down. Then ask yourself if the fear was justified or if you just chickened out.

There are dozens of people I’ve admired and wanted to meet. But I avoided reaching out to them because I didn’t know how to add any value. It’s probably one of my limiting beliefs, but next year, I won’t think twice about sending them a note. I like this quote: Move in the direction of your fear, and the death of it is certain.

Interviewing Sahil Bloom on stage in front of 800 people (someone I’ve admired for a long time)

6. What created energy this year? What drained energy?

Nobody can sustain doing something for long periods of time if it drains them. And it’s never productive to try.

The smarter way to approach it is to identify the activities that drain you early on.

For this question, make two lists. One for things that gave you energy (certain projects, specific people, activities). One for things that drained you (meetings that went nowhere, toxic relationships, obligations you hate).

Then do more of column A and less of column B in 2026.

For me: I’m energized when I meet weird, quirky, and contrarian people who are up to extraordinary things. Drained when I spend time with people who are single-dimensional, overly transactional, and uninspired. Two sides of the same coin.

Our co-hosted dinner with Henrik Werdelin, founder of BARK (BarkBox), Audos, Prehype for a group of 10 entrepreneurs.

7. What will you bring with you into the new year?

Not everything from 2025 should come with you, and this question helps you identify what’s worth keeping. Think through the habits, relationships, and mindsets that served you. If something helped you in 2025, make sure it’s part of your 2026 plan.

My goal this year was to see my parents four times (read: The Tail End), no excuses - and I did exactly that. I took them to Portugal, invited them to New York, and joined them in Hong Kong and Toronto. It’s the most time I’ve ever spent with them post-college, and something I want to continue doing for the decades to come.

I love these guys

8. What will you leave behind?

The other side of question 7. What needs to stay in 2025? Bad habits, toxic people, obligations that don’t serve you anymore, self-limiting beliefs. Write them down. Maybe even on a piece of paper, then burn the paper. You’re not bringing this stuff into the new year.

My realization: My calendar this year was an absolute mess, and next year I want to be more ruthless with how I manage my time. I was perhaps a little too generous with my time, said ‘yes’ to too much, and need to cut back.

9. What are you excited about?

You don’t need to ‘reflect’ too much on this one; it should be immediately clear.

If not, that’s a different issue (you should participate in more things that genuinely excite you)

Maybe it’s a new business idea. Maybe it’s finally getting healthy. Maybe it’s something totally different from what excited you 12 months ago. Whatever it is, pay attention. Your excitement is a clear indicator of where you should spend your time.

Mine: We’re launching a few new projects next year that I’m pumped about. More to come soon.

10. What is one moonshot goal you have for next year?

At Google, we had an entire department called Moonshots dedicated to working on the delusionally optimistic, but unrealistic ideas that, if successful, would have extraordinary positive impacts.

You should have a moonshot, too - a goal that, if accomplished, would change everything for you.

For the last few years, I’ve been thinking about starting a new project beyond events, beyond media, beyond community. It would involve me investing a significant amount of my personal capital and time, but the outcome, if successful, would be asymmetrically enormous. I hope to have an action plan together by Fall 2026.

Take Action

I’ve done this exercise every year for the last decade, and it’s frankly changed my life.

Some years, the answers surprise me. Other years, they confirm what I already knew but was afraid to admit. Either way, it works.

If you want to get even more out of it, do it with a small group. Go through it individually, then get together and share your answers to come up with a plan to keep each other accountable.

This is how you prepare for 2026 to be the best year of your life.

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📌 Andrew’s Bookmarks

My favorite links to help you be wiser and more creative.

Steam, Steel, and Infinite Minds – A short essay on the history of ‘innovation’, where we are in the AI cycle, and what the future might look like by Notion CEO, Ivan Zhao.

So What’s Going to Happen to Product Management Anyway? – A valuable read for those working in PM - esp. if you want to see where the puck is going. With AI, ‘Product Management’ as we know it may be one of the functional areas that will transform the most over the next decade.

How to be Legitimate – ‘Kingmaking’ and the hidden art of building credibility and influence from the lens of Venture Capital and Silicon Valley.

Flounder Mode – A profile on Kevin Kelly (Co-founder of WIRED magazine, author, advisor to Steven Spielberg, polymath community-builder, artist, athlete) on how to follow your curiosity and build a multi-hyphenate career. Naval Ravikant called him the modern-day Socrates.

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🖼️ Behind the Scenes

I went to a different kind of event the other day - a meetup for Alaskan Klee Kai dogs and their owners.

Most fun and hilariously cute thing I’ve done in a while..

It was hosted in the beautiful Madison Square Park - my favorite landmarks in NYC. The history is fascinating btw: the stunning park we see today used to be a swampland, before turning into a refuge for juvenile delinquents. It wasn’t until the 2000s that Danny Meyer (Founder of Shake Shack, Eleven Madison Avenue, Union Square Cafe) raised money to transform it into what it is now - and built New York’s best restaurants around it. Thanks Danny.

P.S. If you have a young dog in the area, Jasper is always looking for new friends.

Spot the difference