Self Determination Theory - The Long View
Much like the graphic accompanying this blog, the path of entrepreneurship is anything but linear.
I started this business with very little—just a dream, a dangerous neighborhood, and a young family to support. In those early days, I operated entirely from a scarcity mindset. Every dollar mattered. Every minute mattered. And if I’m honest, that mindset is hard to shake.
Even now, I find myself questioning: Are those same constraints still real? Or is it just habit that makes every small decision feel like a life-or-death calculation?
Lately, I’ve been feeling a particular kind of frustration. We’re still in the phase where setting the vision and executing it mostly falls to the same few people. There’s a noticeable gap between sensing market opportunity, translating it into executable strategy, and then actually getting it done.
This creates friction on two fronts:
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It slows our ability to scale.
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The only real solution is developing more people—which is expensive, time-consuming, and comes with real risk.
Still, we’re leaning into that challenge. Hard.
Building the Internship Program
One of our biggest current initiatives is scaling up an internship program that we hope becomes a long-term cornerstone of our business. Our reasons for investing in this program are clear:
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To infuse the company with fresh energy and ideas
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To give back to the community by developing the future workforce
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To add bandwidth during a demanding season
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To grow the leadership skills of our managers
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To create a pipeline of future talent
We’re building on the momentum from last summer’s interns. This year, we’ve expanded the program and are partnering with the Warner School at the University of Rochester to train our team—myself included—in how to create a more autonomous, motivated work environment. Eight of us are participating in this training.
Self-Determination Theory: A New Leadership Framework
The training is grounded in Self-Determination Theory (SDT), a framework for understanding human motivation. At its core, SDT argues that people are driven more by intrinsic motivation—things like meaning, growth, and mastery—than by extrinsic rewards like pay or praise. And intrinsic motivation grows when three needs are met:
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Autonomy
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Competence
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Belonging
Scaling intrinsic motivation across a team is proving to be a real challenge.
Personally, I thrive on autonomy. I’ve developed strong competence through years of grinding it out. It’s why I started the business and why I often operate at a pace that intimidates others. But leading a team that’s still finding its rhythm requires patience. And that’s where my old scarcity mindset gets in the way.
I find myself torn between two conflicting mental strategies:
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One part of me is building a business for decades to come.
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The other part still worries about this quarter’s cash flows.
The Long Game
If we’re serious about long-term success, understanding and mastering frameworks like Self-Determination Theory won’t just be useful—it will be essential. Especially as younger generations enter the workforce with different expectations, values, and motivations.
So for now, I’m learning to give the team what it needs most: time. Time to grow, time to learn, and time to develop into leaders who can one day set the vision and carry it forward—without me. I need to establish an operating cadence that prevents irreversible failures while creating space for experimentation, risk-taking, and transparent reporting... I currently do not have that figured out, it's just as much my own mindset as it is the procedural cadence of the company.
As always, thanks for the read!
- Ben
Ps. I am curious how other entrepreneurs went from working in the business, to working on the business, to CEO/Operate the business, to chairman/shepard of the board.
