🚃 👨‍🍼 When to keep going vs. when to quit, and feeding your soul while getting stuff done

Hey Friends,

I’m returning this week from an around-the-world adventure and feeling lucky to get back into a routine I love. I saw my family in Boston, set off to a wedding in Thailand, stopped in Hong Kong, went up to Cerro Gordo ghost town, and landed back in Colombia a week ago.

Highlights of the trip were, getting the honor to write and read a poem at the wedding, and re-exploring Chiang Mai, a place I had lived in a few months 10 years ago. I loved Thailand much more this time mostly because I had curbed my expectations of being able to connect with the local Thais, and embraced the amazing food, adventure, and convenience available to travelers.

The past year for me was full of trying new projects and figuring out what to continue with, and what to drop. In this newsletter, I wanted to share my framework for experimenting and exploring what’s next.

When to keep going vs. when to quit

The common advice says when you start something, you should persevere no matter what and keep going.

Big disclaimer here, for the most part, “keep going” is usually the right advice when you’re at the beginning of most things. The path is unknown and you’ll need grit to overcome obstacles rather than starting over.

However, there is an art to the pivot and knowing when to quit that people don’t talk about enough. Especially when you’re in a pathfinding phase and hunting for conviction.

For those who are constantly inspired and find it easy to start things, I recommend when you start a new project to put a date in the calendar 3,6,12 months in the future as an off-ramp that gives you a license to drop it, or take it to the next level.

At this pre-set point, you’ll have given yourself the time to get through multiple obstacles, get more information, and open up a broader purview of what’s available, all without the hesitation of second-guessing yourself.

There is so much more energy available to you when pivoting is not an option during your commitment, and you may find you can get much further, so make commitments you can keep.

One year building venture scale web3 company

About two years ago now, I wanted to see what building a venture-backed company would look like. This was especially interesting to me after exiting a business that I had bootstrapped. A venture-backed business felt like a potential next step. (In retrospect now it was much more of a diagonal step, than an obvious progression.)

To set up the experiment, I gave myself one year to get as far as I could on a venture-backable web3 startup.

I created a check-in point when the prototype was done to see if it made sense to continue. I gave it 100% while working on it - I joined an incubator to explore the idea, wrote a white paper, recruited collaborators, attended and won a hackathon, pitched to investors, and shelved any incoming ideas that wanted to compete for my attention.

When the time came to check in it was a very clear "no" on continuing. I shut the project down and walked away with lots of lessons.

Meditation Bowl Project

Another example, this past year I set off on creating a new invention that I would then sell in the way I had made my maps. I gave myself 6 months, a budget, and put a date on the calendar of when I would check in.

After 6 months, I had a custom copper sound bowl on my desk and a whole bunch of new skills and lessons from creating this project from scratch, (including 3d printing which I still love).

I then directed a mini-commercial to test interest in the project.

I was trying to find out whether I could sell the product via direct ads. After allocating ad budget to the video, getting all types of tips, and working with agencies to try administering the ads, I found out that the difficulty level of getting this off the ground was not worth it.

Luckily I had a pre-set time to check in.

It’s hard to kill your darlings, especially after ceaselessly putting energy into them, but I decided to drop it.

In this case, it felt like much more of a pivot. All the learnings, conversations and connections led me to a next project of working on a board game with YouTube channel. I connected the dots, brought the right experts into my life and found a project that I felt aligned with.

One-in-one-out

As an add-on to this framework, I suggest keeping your experiments to a maximum of one or two at time—ideally no more than one in each area of your life.

I've read books and articles that try to encourage creative generalists to embrace constant meandering. I don’t agree with this.

While you have to let yourself do some exploring, the idea of letting yourself completely go is a recipe for feeling unfulfilled and having a shelf of half-finished projects.

If you want to add something new, then remove something at an off-ramp to make time and space.

One-in-out.

It sounds easy but it’s hard for when you’ve already invested energy. The default for most people is trying to juggle everything and add without removing.

80% rule for play!

There is another caveat to this. If you're helplessly curious like me, you will have no choice but to make space to exercise that curiosity, or your soul will shrivel and die 🪦.

I've tried to put myself on blinders, and it's maintainable for a while, and then my soul and body start to rebel. One time I gave myself nerve issues from overusing my self-discipline and ignoring what I was finding interesting in the moment. It took me months to recover.

My solution to this is to create a space where you can shamelessly dabble, meander, and explore.

In my case, 80% of the time I’m working on something I’m taking seriously and the other 20% I do whatever I feel like, picking up and dropping things at a moment’s notice. This is soul space!

This keeps me sharpening my focus and making progress in one direction while feeding my endlessly curious appetite. It also incidentally allows me to uncover new hidden opportunities. Ones that may be slotted in for a main project in the future.

Play is a way to see into the future!

That’s all for today!

Thanks for reading - I hope it was helpful! Happy exploring, and don’t forget to enjoy whatever step you’re on and give it 100%.

---