The gap between how we imagine the world works and how it actually works becomes visible when something fails. That gap runs through much of my conversation with Seth D. Allen. We talk about choosing a life that fits who you are, learning from failure, understanding where you work well, building with other people, and giving yourself enough time to become better at what you do. His experience offers a useful way of looking at entrepreneurship as a process of learning about the world while also learning about yourself.
Seth describes himself as an entrepreneur whose work has been shaped by three ideas: freedom, choice and curiosity. He studied law, moved into IT sales and eventually discovered that the professional path he had inherited from the people around him did not fit the life he wanted. That realization led him toward startups, innovation and a series of projects built around human needs. At the time of our conversation, he was developing Medeo, a company working on supply-chain innovation in the vanilla industry in Madagascar, alongside charity and consulting work.
A large part of our discussion revolves around the difference between choosing a career because it looks attractive from the outside and choosing work that fits the way you actually operate. Seth grew up in a family with Caribbean roots, with a father from Jamaica and a mother from Barbados. Education represented a route toward social mobility, and law appeared to be a sensible professional direction. University eventually gave him enough distance to examine that choice for himself.
His first attempt at building a startup became one of the experiences that changed how he thought about entrepreneurship. He developed an education business aimed at universities and students in African markets, reached the MVP stage and traveled to Namibia to present it to universities. The response was encouraging. Then came the harder part: turning an idea and early validation into an operating company. He began looking closely at the sales cycles, relationships, resources and capabilities the business required. The distance between the company he imagined and the company he was prepared to build became difficult to ignore.
“For me, that’s the biggest gap I’ve had in my life between my perception of what I was able to do and the reality of what I was able to do.”
Seth D. Allen
Failure, in Seth’s view, becomes useful when we examine what our assumptions missed. A failed project gives us information about our understanding of customers, markets and our own abilities. That perspective also changes the questions we ask afterward. Where did our picture of the situation differ from what happened? Which capabilities were missing? What would we approach differently the next time?
The experience pushed Seth toward greater self-knowledge. He began paying closer attention to the environments in which he performs well. One discovery was particularly relevant to entrepreneurship: working alone did not bring out his best abilities. He describes himself as an observer and an abstract thinker who listens closely, connects information and works well around other people. Once he began designing projects around those characteristics, collaboration became part of how he worked rather than an addition made later.
“The minute I realized in my life journey that I worked best with other people and I actively sought out that collaboration, that cooperation, that back and forth, that team approach to to things. You know, from an external perspective, that’s when my kind of success hit rate on projects on whatever I was doing really started to climb.”
Seth D. Allen
This leads us into another theme of the episode: the temptation to copy somebody else’s model of success. Entrepreneurship gives us endless examples of founders whose careers appear to provide a template. Seth’s experience suggests a different question: what type of environment allows us to contribute at our highest level? Two people can pursue a similar business outcome through very different ways of working. Understanding that difference saves energy and helps us choose collaborators, roles and projects more intelligently.
Books have played a large role in Seth’s thinking. He mentions Principles by Ray Dalio as particularly useful because Dalio connects abstract thinking with systems for making decisions and operating in the world. He also discusses Turn the Ship Around! by L. David Marquet, whose account of leadership aboard a nuclear submarine led Seth to think about organizations capable of functioning beyond the person who created them. The idea fits naturally with his growing interest in collaboration and in building structures that continue to create value over time.
Patience enters the conversation from the same direction. Building a company takes longer than the early excitement around an idea suggests. Developing ourselves takes longer as well. Seth connects the two processes and raises a question that business conversations sometimes leave in the background: what kind of person are we becoming while pursuing the result?
“That to kind of be a great person is is a worthy goal as well, and that’s really the work of a lifetime, and it has takes a lot of intention. So, the objective success, yeah, great, not built overnight, but don’t forget the self-development, and don’t forget that, you know, we we owe it to the world to to be net positive and wherever we are, not just we built a great business, but are a horrible human being.”
Seth D. Allen
Toward the end, our conversation returns to people. Deals end. Projects change. Careers move through several versions. Relationships, collaboration and the way we affect the people around us remain part of the story long after an individual project has disappeared.
Seth’s journey also leaves us with a practical way of thinking about failure. We can treat each difficult result as information about the distance between our expectations and reality. Then we adjust. We learn more about the environment, become more accurate about our abilities, involve other people where their abilities complement ours, and continue working with patience. Over time, the picture becomes more accurate. And our choices become better aligned with the person we have learned ourselves to be.
Main ideas
- Failure shows you where your perception differs from reality. When a project fails, examine the assumptions you made before it started. Ask what you expected to happen, what actually happened and where the difference came from. Failure becomes useful when you process it and use what happened to improve your understanding of yourself, the market and the situation you are working in.
- Know yourself well enough to choose work that fits you. Pay attention to what gives you energy, where you perform well and which environments bring out your abilities. A career that looks attractive from the outside can still be a poor match. The better you understand how you work, the easier it becomes to choose projects, roles and environments where you can contribute at your highest level.
- Build around your own abilities instead of copying somebody else’s template. Two people can pursue the same outcome through very different approaches. Look at how you naturally create value. You might work better independently, through collaboration, by connecting ideas or by organizing people. Design your way of working around those characteristics and improve them through experience.
- Collaboration expands what you are able to build. Being honest about your limitations helps you see where other people belong in the picture. When you recognize what you do well and where you need support, you can choose collaborators whose abilities complement yours. This changes the way you approach ambitious projects and reduces the pressure to handle every part yourself.
- Give worthwhile work enough time to develop. Companies, careers and personal abilities develop through repeated effort over long periods. Patience becomes part of the process. Stay consistent, keep learning from experience and adjust when reality gives you new information. Along the way, pay attention to the people around you and to the kind of person your work is helping you become.
Links & Resources
- Seth’s Website
- Seth on Linkedin
- Principles by Ray Dalio
- Essentialism by Greg McKeown
- Turn the ship around by David Marquet
- The Bible