Project Recap: September 2023 – March 2024
Before losing my tech job last August, becoming an independent consultant had lived rent-free in my brain for years.
“Will going independent help me live the life I want? “
“Will it help me work on projects I’m energized to work on? (Knowing that not every project will be as exciting?)”
“Will it allow me to use my expertise in a way that helps organizations and people whose values I align with?”
“Will I burn out like how I did at my last job?”
Since going indie, I don’t know that I have the answers to these questions. Just more questions:
“I like the flexibility I have right now. How can I sustain myself financially to maintain this flexibility?”
“Seems like nonprofits have an opportunity to build a tighter feedback loop between their strategy and operations/execution. Can I help nonprofits here?”
“What can nonprofits learn from product? What can product teams learn from nonprofits?”
From product managing complex website projects with Google, Stripe, and IBM to now doing org development work with organizations like Donors of Color and the Global Climbing Initiative… it’s been exciting an leap thus far.
Here are some projects I’ve worked on.
I’m currently taking clients! If you want to work together, I’d love to hear from you.
The Global Climbing Initiative — Organizational Development
Last January & February, I worked with the Global Climbing Initiative to support two existing climbing organizations in the Philippines: the Cebu Rock Climbing Community and the Iloilo Climbing Community.
Veronica Baker Amores — GCI’s Executive Director — and I supported the CRCC and ICC in crafting their vision, mission, and priorities. Both orgs were so down to do the work.
Both organizations love climbing. (So do I.) And they faced similar challenges: what do we want the future of our crags (rock climbing areas) to look like? What type of climbing community do we want to foster? How can we better steward our areas? What political, societal, and cultural barriers are in the way of us seeing through the future we want? And how do we overcome those barriers?
This work has had a few knock-on effects. Iloilo was inspired to formalize their team with an officer election, Cebu Rock Climbing’s crag improvements inspired climbers in Manila to initiate a similar effort.
I mean. Dream project right here. To say the least! As a Filipino American, and as a passionate climber, I feel honored to have played a role here.
Shoutouts to Veronica for being an awesome collaborator and friend. She’s continuing to steward this org development work. I’m constantly impressed by the different horizons she operates from.
And shoutouts to Cebu Rock Climbing and Iloilo Rock Climbing for laying their foundations.
More photos here.
Donors of Color Network (DOCN) — Organizational Development
DOCN is a space for high-net wealth donors of color who want to advance racial justice. Their staff is all BIPOC, majority female. They just finished their 2024 strategic plan. I was fortunate to be brought in to help them think about how they want to work to achieve this plan;
I facilitated the staff through two questions:
What can you do now to move forward your 3-year strategy?
The staff framed work efforts for 1 year, 1 quarter, 1 month, and 1 week with the strategic plan they made. (Inspo: John Cutler’s 1-3s approach to structuring work.)
The template they used looked like this:
What organizational challenges are in the way of doing this work?
They then reflected on organizational challenges in the way of their strategic plan. Where are we stuck? What patterns aren’t healthy that we want to change? We used the Tension and Practices cards to have this conversation.
The team didn’t work cross-functionally but knew they needed to. Well… why? Ah… because priorities weren’t super clear. Each role was accountable for its own “function”, but it wasn’t clear how it all laddered up to DOCN’s larger outcome of nurturing a community for high-net wealth donors. Now that the strategic plan was in place, it was a good opportunity to install some new practices that would catalyze the team to work across functions.
The staff crafted three experiments that they’d try for eight weeks. We used this framework:
The experiments were:
All deadlines would be on the company-wide calendar.
Why? To help make priorities more clear.
Everyone refers to and updates a single doc for all DOCN-related events.
Why? To avoid overlapping events and increase support for each event producer.
Weekly meetings would be structured such that anyone can bring a problem or challenge that the team can collaborate on together.
Why? To prevent solving the problem on your own and increase problem-solving.
Grateful for the DOCN team. They are doin’ the work.
Developmental Editing for the Strategic Independent
I’m thankful to have done some developmental editing for Tom Critchlow’s upcoming book, The Strategic Independent! I’ve been a reader of Tom’s blog for years now. It was awesome to bring my experience as a consultant and as a writer to help out someone whose work I admire.
What’s unique about this book is that Tom has been publishing each chapter on his site. I mean, who else publishes chapters of their book before it’s even a book? Tom’s a big believer in working in public and his book is a testament to that.
Since the content was all there, we focused on nailing the throughline and flow of the book. Developmental editing! Our goal was for the book to feel cohesive and flow before he brought the manuscript to another editor focused on detailed work.
We had four working sessions, with two main goals: nail the big idea and the “acts” of the book. I won’t go into too much detail here, but both of us felt the big idea and acts landed at a good place.
His current editor read the manuscript and was impressed. 🔥🔥🔥
Thank you Tom for the collaboration!
Rock and Rice
I started a podcast! It’s a podcast where Filipino climbers tell their story.
I’ve gone deep into climbing in recent years. And I’ve met tons of Filipino climbers in the States and now in the Philippines. There are so many of us who have our own unique stories and lived experiences. And yet, traditional climbing media doesn’t really feature Filipino climbers. So… why not have a podcast about us?
3 episodes are out now. 257 followers on Instagram as of this writing and 477 downloads so far. Most listeners are in the Philippines! And the feedback has been awesome.
Taking new clients
If you’re interested in working together, I’d love to hear from you: timcasasola@gmail.com.
I’m also open to introductions! If you think of someone that might benefit from working with me, let me know.