Where you wonder if this entrepreneur thing is actually worth it.
You've spent the last 8 hours working on some mundane thing like a blog post, or some crazy technical research into how Postgres JSON querying works, knowing that one day this will pay off, way later down the road.
But then you just cringe at how much time you spent on something like that. Nobody else is doing that. They are living normal lives, but you are putting yourself through some masochistic pain because you're an entrepreneur.
In 2018 I ran for 100 days in a row, but towards the end of the year, I pretty much stopped running.
In 2019 I really wanted to make running a habit. So I set the following goals:
Run 1000 miles
Run a 1:45 half marathon
Run a 3:45 marathon
I signed up for a half marathon at an active volcano in Indonesia around February and started my training.
Running in Southeast Asia was so hard. They don't really have sidewalks there, so you either have to:
Find a soccer field to run circles around
Run in parks or big public areas
Run on the road and die (jk, don't ever run on the road)
The first half marathon in Indonesia was really hard, my time was over 2:00 and it was so humid, and it was the opposite of flat.
But later in the year, I did run a 1:44 half marathon, which was a personal record and felt so good to do that and hit my goal!
A humbling marathon
I ran the Lisbon marathon in October and did HORRIBLE. I wanted to hit 3:45 but didn't even crack 4:25. At mile 18, I hit a wall and could not run anymore. My legs gave out and I pretty much walked the rest of the race.
I never felt pain like that before. I literally could not run anymore.
The whole experience was really humbling. To be totally honest, I went into that race with hubris, overconfidence, and I got kicked in the ass. It was actually kind of nice to be humbled like that.
I also didn't take my training seriously. I skipped and skimped on lots of long runs, and I thought I would be fine.
Regardless, that failure has given me the motivation to turn around and do the LA marathon in March. My goal, again is 3:45.
Just getting used to it
I remember running every day feeling really hard back then, and especially in 2018, but thing I loved about 2019 is that running just became so much easier because I was running every day.
Nowadays, I can run every day with no problems at all.
Generally, I'm in really good running shape after all this running. I'm not a great runner though, but for me, I'm the best I've ever been.
Goals for 2020
In 2020, I want to run a 3:30 marathon. 3:45 in LA and then I would like to do the New York marathon, but I need to figure out how to get in.
I'd also like to run 10 miles a day for a month, or a 10k/day for a month as a fun thing.
In 2019 I ran in so many places! Here is everything I can think of on the top of my head:
Ran on 3 continents (North America, Asia, and Europe)
Ran in 8 countries (USA, France, Portugal, Spain, Indonesia, Vietnam, Thailand, Singapore)
Ran in countless cities
Favorite city to run in: New York City Least favorite city: Canggu, Bali
As far as miles and stats, according to my Strava:
I ran 221/365 days, or 60% of the year.
I was also running for 200 hours, or 8 full days, more than a week! I was running for 2% of 2019, that's insane!
I forgot to write a journal entry yesterday, I need to start writing these in the morning, or at least drafting them.
As a part of my rule, any missed journal entry means I have to donate or support someone or something.
Today, I'm donating to Postgres, an open-source database tool I have used extensively over the past 4 years. I've used it for every single project I've ever worked on. It's an amazing tool that has saved me thousands of hours of work and indirectly generated thousands of dollars.
I'm glad I made that YouTube video because it really got me thinking.
And furthermore, the 2 hour run I went on today had multiple revelations and "aha" moments. That's what I love about running. You just think, for a really, really long time and you can't distract yourself. You just keep thinking.
But I thought about it, and why do I separate the success and money between Starter Story and Pigeon? They are very complementary businesses, and I should treat them that way.
Part of me doesn't want to "mingle" them together because I don't want to muddy the waters, and for example, Pigeon is only successful because of Starter Story, but that is just counterintuitive. I should leverage Starter Story to grow Pigeon.
Why create new blog posts on the Pigeon website, when I could just do it on the Starter Story website, and link back. That solves a couple of really big problems - I don't have to wait as long for blog posts to start hitting because Starter Story has a really strong domain ranking.
And, in the event that Pigeon goes sour, I'm still growing Starter Story and can pivot to new software. Because if I work harder on Starter Story, it will help that platform grow a lot, too.
So, from a high level, I will start looking at my revenue as a whole. As Pat Walls LLC. More focus on Starter Story and bridging the gap for Pigeon.
So, what's the new plan?
Stop blogging on Pigeon's website
Stop doing Quora answers - it's not working
Start writing blog posts on Starter Story
One blog post/day
Write really high-quality stuff, learn a lot more about SEO
Get good enough to start outsourcing and automating that
Start driving some traffic from Starter Story blog posts to Pigeon
Start doing outreach to events managers, "string quartet" types, and interview sites
When that outreach doesn't work, turn around and put them through Starter Story - maybe we can get something out of that
Put off the side project marketing until February
keep doing case studies
focus on the tools SEO project, and generally more "automated content"
Today was the first "real" (non-holiday) day of the new year - and I was able to work from the Salt Lake City library - probably my favorite place to work of all time.
As stated in a previous post, I'm going full-on on Pigeon marketing. Less product development and more marketing.
I'm trying to be more cognizant of how I spend my time, so that I'm not falling back into the trap of only doing product stuff. My goal is to be spending 75% marketing and customer support and 25% product development
So, here's the big things I did today:
Posted 5 Quora answers + 1 lookalike Quora blog post
Reached out to 6 Pigeon customers to ask them to do case studies
Finished the draft for my big outsourcing blog post
Worked on Pigeon file attachments feature
Overall, I felt less productive. I don't like working on the marketing stuff as much as I do the product stuff, so it's something I need to get used to. The more I do it, the more I will get better and focused.
(this is an email I sent to some stakholders for Starter Story)
Happy new year! Usually I send out a monthly report, but for this month, I want to share some of the numbers for 2019, as well as our plans for 2020.
Unique visitors: 709,605
Total Interviews with founders: 744
Total Mailing list: 10,535
Email newsletters sent: 567,180
Revenue generated: $63,926
Those are just the numbers, there are so many amazing things we did that can't be measured as easily, like building a team, our growth in SEO, and the countless people we inspire every day to start and grow their own businesses.
Focusing on 2020, here are our big goals:
1. Increase content output to 180/month by the end of year.
By the end of the year, our goal is to get to 180 interviews/pieces of content per month. Currently, we are doing about 60/month, so that's a marginal increase of 10/month. To do this, we will be adding more people to the team, building more automated ways to publish content, expanding to new content types, and expanding to new business domains/topics/and countries!
2. Reach 500K monthly visitors by the end of the year.
In 2019, we grew from 30K visitors/month to 120K visitors/month, a 4X increase. By the end of the year, I think we can hit the 500K number.
3. Increase revenues to $15K/month by the end of the year.
To do this we will keep working on the premium membership, affiliate revenue, and opening up more opportunities for sponsors.
Those are the big goals! Simple, but lots of work to get there!
With that post, I felt like I was coming out to the world about some really big life and career changes (quitting my job, starting my own business, going digital nomad, etc). It was a really exciting time for me.
Fast forward to today - there’s just one day left in 2019, and I feel like I have to write one for 2019.
But 2019 was not “the best year of my life” - maybe I wish it was - so I could write a post that would top last year’s.
2019 was just very different. It was my first year working full time on my own business, setting up the foundation for a (hopefully) prosperous next 20 years as a founder.
This recap probably won’t be as exciting or inspiring as last year’s, but here it goes…
I met countless other people I had only known through Twitter and made some amazing friends and relationships.
But I’ll be honest, I sucked at being a “digital nomad”.
I found myself getting pretty depressed. I had this weird dichotomy where I really wanted to travel and experience new things, but I also really wanted (and needed) to work on my business.
So, although I was in these new amazing countries and cities every month, I was pretty much just working all the time.
Looking back, working on my own and not having a job was just so new to me, that I couldn’t comprehend or justify not working. I couldn’t relax.
I worked a lot.
Since I didn’t have a “real job” I lost the concept of normal working hours, and of weekdays, holidays, etc. All the days started morphing together into this crazy blob.
Looking back, I feel like I needed to go through that pain and confusion and learning “how to work”, because nowadays I have a far better sense of how to be productive and feel like I’m in much more control of everything.
Through that trial by fire, I’ve become much more productive with less hours, learned how to outsource and build a team (more on that later), and started running a lot.
Killing off all the extra projects
In March, I found myself overwhelmed with the amount of projects I was running.
Fresh off 2018, I had launched multiple 24 hour startups and I was running 4-5 different projects at the time.
It was cool to build and launch so many new things, and it looked great on my Twitter, but it was not realistic, and it did not result in a lot of money, which I need or else I’m back to being a software engineer.
So I decided to make some hard decisions and kill off all my extra projects.
I knew it was time to pick one project and focus nearly all of my energy on it. That was the very early beginnings of what turned into Pigeon (more on that later).
In March I also ran a half marathon at an active volcano in Indonesia.
I really started to get serious about running this year. I ran over 1,000 miles this year! I ran two half marathons, and a full marathon!
Focused in Vietnam
In April, I got to Vietnam, where I immediately got food poisoning.
I spent most of April building and launching my new app Pigeon. I had committed to a small group of customers that it would be ready May 9th. There was so much work to do.
I just remember being really focused in Vietnam. Same routine, nearly every day, for almost two months.
I quit social media (complete cold turkey) for a whole month which was a really fun experience. I quit EVERYTHING - Instagram, Facebook, Linkedin, Reddit, YouTube, everything!
I found myself with so much extra time, and I started reading lots of books! I think I read over 10 books in one month.
Digital Minimalism by Cal Newport
Can’t Hurt Me by David Goggins
Never Split the Difference by Chris Voss
The Millionaire Fastlane by MJ Demarco
What I Talk About When I Talk About Running
Start Small, Stay Small by Rob Walling
Principles by Ray Dalio
Shoe Dog (Nike memoir)
Zero To One
I’m not off social media anymore, but I still don’t have the Instagram or Twitter app installed on my phone. I also muted every single person on Twitter, so I no longer have a feed and I’m pretty out of the loop these days.
I also started a YouTube channel which was really fun. Although I haven’t uploaded in like 6 months (will get back into it in 2020!).
And on May 9th, I also “officially” launched Pigeon to a small set of early customers.
It was a small, “soft launch”, but it felt like a massive milestone.
Building a team & learning how to manage
I spent most of June hiring and building a team for Starter Story.
While Pigeon was new and fresh, it was taking up a lot of my time, all while Starter Story was (and still is) going really strong.
At this time, I was still doing all of the work myself for Starter Story. I realized the only way to scale (both Starter Story and Pigeon), was to get help.
So I spent most of June hiring and onboarding a small team of freelancers to help run the business.
Nowadays, the Starter Story team consists of 3 (+ me) people who do outreach, review and publish the interviews, manage email, and handle most of the day to day tasks.
It was one of the best decisions I ever made, and I can’t imagine being sane without this team (thank you to Gemma, David, and Ella if you’re reading this!).
Starter Story is now a machine that runs on its own, and I think that’s really cool! We are publishing more content than ever before.
At first, it was hard for me to imagine anyone else being able to do these tasks that seems so “proprietary” to me, but I quickly learned other people could do it, and they could even do it better.
I also learned a lot about how to hire people, manage, and onboard them! This process gets me excited about the future and how I can take myself out of a business once it’s running smoothly. It’s really fun.
In July, I decided to end my “digital nomad” journey and come back to the USA.
What I thought would be many years traveling the world ended in about 6 months.
For me, I realized that what’s important to me is freedom from a job and to build my own thing. I don’t need to be in Thailand to have that. I can still have that in the United States, but I can also have all the benefits of being around family and friends.
When I realized that, I knew it was time.
What’s beautiful about it all is that I’m still a “digital nomad”, because I can still work from wherever I want.
After coming back to the US, I spent a month in New York with friends, a week in SF, and a week in San Diego too. I also went to Europe for a month!
In August, I went on the Indie Hackers podcast, which was a pretty surreal experience because it was the website that inspired everything for me.
In September, I also had a very, very lucky opportunity to work with none other than Kanye West, who is my #1 idol in life.
I got to meet him and help out at his new Wyoming ranch for a week.
And I finally made my way back to New York for a whole month. It was amazing to get back.
I took the whole month of October off and traveled through France, Spain, and Portugal with my dad.
It was a great trip, and I’m grateful to be able to take this kind of time off and be able to spend it with my parents.
Rejected from YC, again!
I applied to YC, just for fun (kind of) for my new app, Pigeon.
After my YC rejection a couple years ago, I never thought I would actually get an interview.
But while traveling in Europe, I woke up to this email:
I spent a couple weeks preparing, doing mock interviews, all that stuff, and found myself extremely stressed out about the whole thing.
It was honestly a really hard time for me. As a solo founder, I had to explain to really, really smart people about how Pigeon is a company that will make hundreds of millions of dollars.
And that was really hard. I didn’t think about those things until I got the interview, so I was scrambling.
I felt like I was “faking it”, acting bigger or smarter than I actually was, and they could probably see that.
I was rejected.
The interview was a really intense experience, but I’m glad I did it. I learned a lot.
I know Pigeon will be big, but it’s going to take time. I was sad for a couple days, then I moved on. Back to building a business.
YC HQ in Mountain View on interview day.
In November, Starter Story crossed 100k uniques and almost 140K visitors!
The newsletter also crossed 10,000! Starter Story continues to grow every month!
Starter Story traffic in November, our biggest month ever
In 2019, we published over 500 interviews, and that is all thanks to the team and the work we’ve done to scale the project.
We also became one of the biggest websites in the world, our Alexa rank reached 30k at one point. A bit of a pointless stat, but it does mean that we are in the top 0.002% of websites in the world. Kind of crazy to think about.
I’ll be honest, December has been a bit tough - mainly because Pigeon hasn’t had the success that I wish it had.
Although we had a solid launch, we suffered some big setbacks like the Google security audit, and experiencing some churn.
When users churn, I take it personally, because I put so much of myself into the product and into the future of the business.
But, I’m getting better at that. I’m trying to focus more on the things I can control and I’ve been feeling really good these last few weeks.
With the Google security audit out of the way, Pigeon is now out of beta and open to the world, and I feel really good about 2020.
Over the year, I’ve definitely gone through a few slumps. I don’t think it’s depression, but I think it’s part of being an entrepreneur and the highs and lows that come with it.
When my business is doing well, I’m on top of the world, but when something bad happens, it can ruin my day. I attach myself to the business, it is a part of my ego.
I’m trying to work on that and be more mindful and detached from the day to day of the business.
If you haven’t noticed, I also went a bit quiet in 2019 in terms of social media and how much I share about my business. I still do monthly updates, I just don’t tweet about them or tell many people.
I went quiet for a couple reasons. I’m trying to stay away from social media because it genuinely makes me feel shittier. I often compare my own success to others success and that always brings me down.
The other reason, to be totally honest, is that I wish I had a better story to tell - I wish there was more growth, success, money to talk about. But that’s life.
I also started writing more and plan to in 2020. About a month ago, I started writing an online daily journal, you can find that here.
I’m really excited for 2020.
As far as the business side of things, I am confident 2020 will be the breakout year for Pigeon, and Starter Story will continue to grow and scale.
I’m running the LA Marathon in March.
I plan to move to New York City for the summer, I miss that place and want to live there again. So if you’re out there give me a holler.
This is a follow up to this post and this post, which both address some of my plans and ideas for taking Pigeon to the next level in 2020.
The idea is to actually go and find a "market" for Pigeon.
Pigeon is a great universal tool because it lives in Gmail, but as a bootstrapper, it makes a lot more sense to start with a more targeted niche. One day it will be great to have Pigeon serving hundreds of different use cases (and I genuinely think it can be that) but I need to get real with myself a bit here. I'm not a VC backed startup, but I'm acting and like one in terms of the "go to market" strategy.
In my post from a few weeks ago, I talked about how I scoured the reviews for Streak in the Chrome web store and logged all the different use cases that came up (and how many times).
I finished up with that and built a scoring index in Google sheets based on a few questions like "how big is the market?", "how easy to get in front of them?", etc.
Here are the 3 use cases that we will start with in 2019.
Freelancers and contractors scored highest based on my scoring system, and realtors didn't score that well, but they appeared the most in the reviews.
I will test these markets for the next 3 months. January, Feb, and March. After 3 months, based on my results, I will decide to keep targeting these markets, potentially drill down further into a more specific niche (i.e. commercial realtors) or go for a new niche altogether.
Last year, I set really ambitious goals for 2019. Although I hit a lot of them, the goals were too expansive and specific, like hitting $X/month in revenue, running 1000 miles, publishing X YouTube vidoes, etc.
It was good for last year because I didn't really have a good vision for what I wanted to do in life. But in 2019, I figured out my more "overarching goals" which are to build a successful business, spend time with family & friends, and fitness stuff. My goals are more about the next 5-10 years and I'm very focused on that.
I'm also a lot more confident in what I want out of life and I really don't need "goals", because I'm dedicated to working on these things every day and they are basically habits for me now. So, I'd rather set monthly goals and these often become weekly and daily goals embedded into my brain.
So, for 2020, I'm not going to set goals like that. I'm not really going to set any goals.
However, one thing I want to get better at is spending my free time on more interesting things and improving myself as a person, as well as learning new things and keeping my life interesting and my day's invigorating.
So in 2020, I want to dedicate each month to learning a new hobby or subject, or trying something new, and just "immersing" myself into it.
This is my personality - I find something new and get obsessed with it. I really enjoy learning about new things. So, I want to take advantage of that (but also not let it take over my daily life).
So, on evenings after a long workday, I want to have some new hobby to look forward to that is productive. Something to do with my extra hours that gets me excited.
Each month I will pick a "thing" and research it and execute on it.
I don't know exactly what they will be yet, but here are some ideas:
stand up comedy
learn an instrument
learn a new language
Run 10 miles/day
5am wake up
Read x books
get into anime
get into short stories
schedule my entire day
something with vlogging/Youtube
As the year goes by, I will keep thinking of more based on new things I learn and get excited about.
At the beginning of the month, I will pick something and create a mini-plan, and plan to dedicate some time to it every day, if needed.
For January, I pick cooking. It's good timing for me because I am living at home with full access to a kitchen and I'd like to save money, learn more about meal prepping, and I'm counting calories to lose weight for my marathon in March.
I came across this blog post yesterday which felt like a bit of a wake-up call.
Especially, this excerpt:
To keep growing, to keep living even more deeply and authentically into what makes you come alive, invite yourself to risk what brought you to where you are today.
2018 felt like my breakout year. I took massive risks, built a new business off the ground, quit my job, launched some huge projects like the 24 Hour Startup.
But 2019 didn't feel like that.
It felt a bit like I crawled into a hole and hid away. I picked a new product to work on and didn't talk much. I didn't tweet much. I didn't put myself out there as much.
I think this is partly due to fear of what people thought about me.
I'm not regretting it, but I think my success shocked me a bit. It made me feel like I needed to keep "one-upping" myself.
This is not necessarily a bad thing - the new project I was working on was the antithesis of this mentality. It is a project that takes time, and there will be no breakout success. So, going heads down is essential sometimes, all creators do it. 2019 was about working hard and not talking much.
I'm really hard on myself. Because I'm so focused on building Pigeon, I tend to forget about my success and all of the things I've done in the last couple years.
When people ask about how things are going, lately, my answers are something along the lines of "good, not great". But the reality is that things are going great if you compared them to 1 year ago.
It's just that the novelty has worn off that "I started my own profitable business, live my own life on my own terms, and make almost $100k/year doing it." I don't even want to tell anyone anymore that.
It's never enough - sure that is a good poisition to be in right now - but will it be there next year? Could it all fall apart? Yes, that's why I need to focus on bigger to make up for that. I don't want to "do OK for myself" but have to go back to the corporate world in 10 years. I work so fucking hard right now so I don't have to work ever again past 40 years old.
All I care about is the success of my new project, and I won't be happy until I can tell people that it's successful.
The issue is that the "success" of Pigeon has taken longer than expected, and may take another 1-2 years. I can't sit in silence that long. I think about how I'll finally "come out and tell the world" when I hit $5k or $10k/month, but that might be a really long time, and I need to figure out a way to put myself out there while I work on that.
Because the reality is that putting myself out there is the best thing I can do, both for myself or my business.
I need to remember that nobody actually gives a fuck. I have this impostor's syndrome that my Twitter following will see me as a fraud, because I couldn't be successful with my new project as fast as the next wildly successful SaaS founder.
I need to be comfortable with losing it all. With losing all my "cred".
From the article:
Who are you willing to continue to become, even after you’ve accomplished some success? What are you willing to risk, to continue going in the direction that is calling you?
Will write about this more. I think there is an easy solution to conquering this, just need to think about it a bit more.
(this is a note I wrote today as part of my plan in 2020 to focus on marketing for Pigeon)
While I was traveling for a couple months, I didn't have much time to spend on development. I think that gave me a glimpse into all of the shortcomings of Pigeon, especially with onboarding, design, and features.
So when I got back, I decided it would be a good idea to focus solely on product. It's been about two months, and we have come very far. Added some massive features, way better documentation, etc.
It was great timing because of the security audit, but now that is finally about to be over.
Product is important, but I think marketing and customer support is more important right now. We came a long way in the last few months with product, I feel so much better about the product right now.
Product is also relatively easy to improve. We can always improve product. But getting the foundations for the marketing is more key right now.
But I remember what it was like when we were posting on Quora every day. That was a bit of a "validation" phase, but it also was great marketing. A lot of experimenting, but now I see the benefits of that relatively small marketing push.
In other words, it's time to focus on marketing. It's time to change my mindset about how to grow this thing.
I know I have some of the skills to have a marketing success, and I think those skills are:
Automation and outsourcing - use those skills to build a marketing machine
I know how to pump out content (from my experience at Starter Story)
How much time should I be spending on marketing? I need to keep myself accountable.
I should be spending 75% of my time on marketing and customer support. 25% of my time on product development.
I need to keep myself accountable for this.
TODO: add a weekly reminder to roughly track activities
How much budget can I be spending?
Put all Pigeon revenue into marketing. Which should mostly be for paying for writers (for content). will address that in a bit.
What are the ways we can "kill it" in marketing in marketing?
It's important to stay focused on a few different ways, but still keep it diverse and try new things, and of course keep it fun!
Here are the things we should focus on:
1. Quora post & blog strategy (25%)
Just like we did before, post on Quora 5 times per day. Find the blog posts that perform the best in google search, where Quora performs the best and build blog posts around those. really easy to automate this one. Outsource/automate as fast as possible. Just need to be careful about spamming and that kind of thing.
2. Blog posts and tutorials (how to X) (specific to use cases) (25%)
These are blog posts that show off the power of pigeon or show users how to do something that would be beneficial, like how to get on podcasts or something similar. These will also be specific to use cases that I pick and deem worth going after (which will be determined soon). Do this myself until I find systems to automate/outsource.
3. Case studies with customers (10%)
This is an easy one. Offer users a free month of Pigeon if they can answer a small questionnaire. This gives them a nice backlink, and I also get to learn more about what they do and how Pigeon helps them. It's a win-win. Easy to automate/outsource.
4. YouTube videos (tutorials) (25%)
These will be mostly recycled from the blog posts and tutorials (always do both). YouTube is a massive channel. let's plan for some fun stuff here too, like emailing all congresspeople or something like that. Take advantage of memes!!!
This is a huge one but should only be done as weekend projects because I don't want to get carried away. First example will be "Block Sender". Launch on Product Hunt, Hacker News, etc. Do it all on my own site, and with Pigeon branding, like "Block Sender by Pigeon"
7. Email marketing / build an email list (5%)
Send update email every week, no matter what. Stay humble, be funny, keep it interesting.
Find use cases and get specific
One huge problem with Pigeon is we don't have a specific market, my plan for that is to find some. So, the goal is to go after 3 different markets with the Quora, blog posts, and YouTube videos, and many more.
I will test these for 3 months. If one doesn't pan out, will pick a new one - if one is working out - then just keep going with it. Always have 3 different running at a time.
(those use cases / segments will be determined by the end of the year)
Set a plan
At the beginning of the month, create and set a plan for how much content we will do. A plan could be like this:
I put about 60 hours / week into Pigeon or 240 hours per month. 75% of that 180. Meaning I should be spending 180 hours on marketing things.
In the first month it might look something like this:
Fully automate and outsource quora strategy
10 blog posts (that are Quora copycats)
4 case studies with customers
4 pillar blog posts / tutorials
4 YouTube videos
Release a chrome extension
Deploy alternatives pages
What should I be doing (every day)?
My focus should be to automate and outsource as much as possible. I should be trying things, seeing if they work, and then building process and outsourcing them. As always, learn myself and start small with a limited budget, having people work on the smallest things first.
Since some big life changes over the last couple years, my "going out" and drinking life pretty much evaporated.
I used to be a big drinker, going out at least twice a week and sometimes having 6+ drinks.
I'm not really sure why this happened, but overall, I just started feeling way less interested in going out. Even when I was with friends and we went out to dinner, I would often bail out before the "big" drinking started.
Or I would just opt out of events that were clearly "drinking just to drink". That's the difference to me. I enjoy going out and doing things, but if it seems like drinking is the focal point of the event (going to a club, house party, etc) then I'm way less interested.
However, I love going to concerts, sporting events, dinners, or even just going to bars with friends where you can actually talk.
One reason why I went out less is I couldn't really justify the hangovers anymore. Having a hangover all weekend is OK if you have a 9to5 job because your schedule is basically built for it. But if you run your own business, your hangover is a liability. Each night out (+hangover) steals 8-10 hours that you could be using to improve your business, or to take some quality time off.
As I stopped going out, I would watch my roommates in pain every Sat/Sunday morning at 10am, vegging out on the couch, ordering takeout. Meanwhile I woke up feeling fresh, got a couple of hours of work in, or even a good run!
And although I might have had some FOMO the night before, I never regretted it after hearing what actually went down because I realized never really missed anything.