4 / Captain's Log: October 2020; Letting the Longing Do the Work

Six weeks ago, I wrapped up my last week as CEO of Holloway to pursue a vague new career made up of a mixture of research, writing, and coaching.

I used Rise Sleep to optimize my day for my energy cycles. I made sure not to book meetings before 11am to use my mornings to wake up, meditate, and study. I’d take a meeting or two between 11-12, take my time with lunch in the noon hour, and then a few more meetings before three as my energy dipped. From 3-5, I’d work on a creative project, and I had big plans for creative projects.

Thrilled by the excitement of starting a new chapter, I bit off more than I could chew. I realized I was cramming a book, a newsletter, a podcast, coaching, setting up the back office for the business, and learning how to do all of the above in two hours a few days a week.

It was clear to me that I’d need to readjust my expectations for this new life.

After the last edition of Letters, Dan Putt emailed me with a quote from Reboot coach Jim Marsden. He said Jim tells folks who are in transition to “let the longing do the work.”

Into a few weeks of this new beginning, I find myself loving coaching more than I expected to.

I've shifted my focus to projects that support becoming a coach, and while writing a book and creating a podcast and all that are still things I'm working on, there's only so much time.


I’ve been throwing myself into books on the subject of coaching, and I want to keep studying. Many coaches have been generous with their time and shared their experiences over the phone or Zoom or long DM threads on Twitter. I'm loving this period of learning and am grateful for all the time folks have been giving.

One friend asked if I’d coach them and their co-founder, giving me my first “practice clients.” Today I have eight clients.

I thought I’d be pouring all of my creative energy into a new book and accompanying podcast, but a “too good to be true” opportunity to combine my love of writing with my new career as a coach materialized after a phone call with a friend. It’s a newsletter in collaboration with a highly sought after coach. The first edition comes out next Wednesday.

As for the book, I think it will still happen, but the coaching and the writing will help me get there a bit more informally.

As for the podcast, it’s still happening in the background. My vision is that it will be like How I Built This, but about the people instead of the ideas. I’ve been riffing on the concept of structuring conversations as one part “post-game analysis” and one part “dungeons-and-dragons.” We’ll pull in founders to talk about how they formed a team (Level 7 engineer and a Level 2 marketer?), we’ll talk about significant peaks and valleys in the relationship, and debrief how the founders feel with the benefit of hindsight. An incredibly talented composer friend is working on the theme music, and I think I know the designer I’ll rope in for the art. I have a few founders who have agreed to come on the show. I’d like to book 10 episodes for early 2021, so if you know any founders who would be willing to do a “post-game analysis” of their experience, I’d love to chat with them.

Finally, I’ve been giving myself time and space to think. For the last couple of weeks, I’ve been spending mornings with coffee sitting on the benches at the top of Dolores Park. I’ve felt guilty about this time because it hasn’t felt “productive.” I almost stopped going until a friend convinced me to keep it up. The next morning, inspiration struck, and I power-walked home where I totally redesigned and shipped an update to my personal site that I am absolutely loving. Check it out here, and please send feedback!

Looking forward to what’s next,

P.S. Thank you to all 80+ people who replied to the last email with offers to help. The internet is such a cool place.

How You Can Help

→  If you, or anyone you know are interested in working with me as a coach. Send me a note at hi@andysparks.co.

→  If you, or anyone you know, would be interested in reflecting on your startup experience with an emphasis on the people instead of the idea for the podcast, send me a note at hi@andysparks.co.

→  Check out my new website here and send feedback here to hi@andysparks.co