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Transformation Through Rest: A Conversation with Olatunde Sobomehin

Date: August 30, 2022

Chloe Heskett

Senior Writer, Editor & Content Strategist, CEP

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A little more than six years ago, Olatunde Sobomehin co-founded the organization StreetCode Academy, a California-based nonprofit that provides technology access, skills learning, and mentorship for communities of color. Since its founding, Sobomehin has led the organization as CEO, overseeing its rapid growth from serving 25 students locally to reaching 3,000 students globally, being named a 2021 California Nonprofit of the Year, and launching the world’s first Philanthropic NFT series.

Now, he’s ready to level up — by taking a step back.

Sobomehin embarked on a year-long sabbatical at the beginning of this year. He sat down with us recently to discuss how the idea came about, how it’s going, and why he believes this time of rest is important — both for him and for the organization — as well as to share some advice for other nonprofit leaders (and their funders) considering the value of sabbaticals.

This conversation has been edited for length and clarity.

Chloe Heskett: Tell us how the conversation around your one year sabbatical came about? 

Olatunde Sobomehin: I’ve been most concerned in life with how I honor God, how I walk with God, first, and second with how I show up to my family and the people I love most. And then, lastly, how I show up to my calling and my work. And I realize I fall way short of those pieces much of the time, so I’m hungry to try and improve on those areas and do better.

I thought I was putting God as the captain of my life, but I realized I was doing that a lot with work, but I was not doing that a lot with rest. I was hit with, what has that done for my family? What’s the return on that for my family? What’s the return on that for me as a husband, what’s the return on that for me as a father? And I was determined to try and right what I feel like I’ve done so wrong.

So, I was extremely committed to doing this .

CH: Yeah, thank you for sharing that. Why, one year, why not something shorter?

OS: I mean I don’t think the timing was a major emphasis for me. I think it’s the rhythm, right? It’s, what is the work-rest cycle in my life going to be?

But the second thing was that when I talked to our board of directors, the year had a very practical approach, too, and the practical approach was this: I had three goals. First was in my personal life: I wanted the to give life to me personally — spiritually, with my family, there were some personal goals I had. Second was professional. I wanted the to open up new professional areas in my life that hadn’t been opened up because I was so consumed with a particular work cycle with my job. Lastly, I wanted it to be redemptive for our company. I wanted StreetCode to be different as a result. And when you have those three major goals, it would be very hard to do that in just two months, or in just one month.

And so we separated the in three areas: the first three months of my sabbatical was a transition. It was literally for me to assist the other pieces of the organization to be able to equip them for the leadership that they were going to take on. The next 6 months was the bulk of the sabbatical, and we call it the academic sabbatical. That was for me to really publish, something that I wanted to do professionally. So, for me it meant writing a book and it also meant me thinking about the business opportunities that I wanted outside of StreetCode Academy. And the last three months, which is what I’m about to go on, is the actual rest piece of it, for me to rest and for me to understand sort of the condition of my soul — to do some real soul searching.

CH: As you’re about three quarters of the way through this time, what’s the experience been like so far?

OS: The last time I reflected about my experience with sabbatical, I was in uncontrollable tears. I was in uncontrollable tears. And the reason why is because it really has been transformational.

And what brought me to tears was the transformation that occurred with my family. The time that I was able to spend, particularly with my youngest son, took me over the over the top emotionally, and so I would say that first and foremost — I would remind the readers, that I had three goals right? It was personal, professional, and it was for the organization, and I wanted it to be transformational in all those areas — and it has been.

The first was transformational in that family time, in that personal time, in that spiritual time.

And then it’s been transformational for me professionally: it’s opened up doors for me to finish a book project, it’s opened up doors for me to level up as a professional in the things that I’m able to do — and to see myself not just as an executive of a nonprofit, but also as an entrepreneur, and also as a researcher. I mean these are things that now I get to see about myself that I didn’t get to see before taking a sabbatical.

And lastly, and probably most important to those of us that care a lot about our work, it’s been transformational for our work. I’ve seen a founding COO become a CEO and run an organization. I’ve seen the organization live and thrive outside of my leadership. That’s really remarkable, and that’s really transformational for an organization to think about its longevity and to think about success, because you have no success without succession. It can’t be just one person, and we’re seeing, and we’re not just seeing but we’re experiencing and we’re witnessing, an organization that is living that out beyond just a founding CEO and I think that’s also transformational. That’s how it’s been for me.

CH: What do you hope will be true both for you and for StreetCode as a result of this journey?

OS: I think the number one thing that I want to be true is for us to understand that rest is a part of the creation process and part of the healthy cycle.inline I do not want to be a person, nor do I want to be part of an organization, that does not understand the role rest plays, and so I want us to understand what that looks like.

CH: Do you have any advice for nonprofit leaders and, importantly, their funders as they consider offering a Sabbatical like this?

 OS: Yeah, I think I think my advice to them is , as we think about the long term, the longevity of our organizations, when we think about the long-term impact on the people we serve, starting with our employees and ourselves, when we think about the whole impact of our communities, I think we should consider the role rest plays in all of that.

And I think when we consider that, I don’t think there’ll be any question about the value that rest .

So that’s number one. And the second piece is that I would encourage people to think boldly and to think courageously about the way in which we can support rest, because there is a significant return on that investment — that’s been my experience thus far.inline

And for those people who believe in God, I would say to allow this conversation around rest to be an exercise in our faith, and to be an exercise in trust, and to be honest about that.

It’s a journey — I’m not prescribing anything to anyone … my feedback to investors and to nonprofit leaders is to consider the longevity, to be bold in our approach.

Olatunde Sobomehin is the co-founder and CEO of StreetCode Academy. He is co-author of “Creative Hustle – Blaze Your Own Path and Make Work that Matters,” available for pre-order now everywhere

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Editor’s Note: CEP publishes a range of perspectives. The views expressed here are those of the authors, not necessarily those of CEP.

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