The Entrepreneur’s Shift From Yes to No
One of the areas where I’ve had to improve is saying no to things. For many years, I defaulted to yes. I would try a new networking group, meet a new person, or evaluate something where I had no prior

One of the areas where I’ve had to improve is saying no to things. For many years, I defaulted to yes. I would try a new networking group, meet a new person, or evaluate something where I had no prior experience. That proved useful because it helped me learn what kinds of people, organizations, and opportunities I actually enjoyed being around. I could quickly determine whether a group was a good fit for my interests or not.
Over time, as I developed a better understanding of what I enjoyed and what I did not, I started taking a more critical view of incoming requests. After having a successful startup, it’s easy to become inundated with invitations to join the boards of nonprofits, charities, and organizations. Initially, I defaulted to yes and would spend time learning more about each opportunity. Eventually, though, I started asking myself a different set of questions: What kinds of organizations do I enjoy most? Where do I add the most value? What types of involvement are most meaningful to me?
On the nonprofit and community side, I learned that my primary interests are economic development, quality of life, and entrepreneurship. Once I viewed opportunities through that lens, decision-making became much easier. I could compare requests against the areas I already knew energized me and make more intentional decisions.
On the entrepreneurship side, I receive requests related to all kinds of businesses. In some cases, I have highly relevant experience. In most cases, I do not. When I do have relevant experience, I can share lessons learned and discuss what worked and did not work in prior ventures, especially in the context of stage, size, and scale. When I do not have relevant experience, my default answer is now, “Sorry, but I can’t really help.”
As a result, I say no far more frequently than I used to. There are certainly entrepreneurial lessons that apply across almost every business, such as culture, scrappiness, hiring, and market dynamics. But I generally do not find it worthwhile to engage if that is the full extent of the value I can provide.
I’ve also learned that I enjoy maintaining a more flexible schedule. Having the ability to dive deeply into whatever the important topic is that day or week, or immerse myself in a new idea or venture, brings me far more energy than having a calendar packed with back-to-back meetings. This perspective also shapes how I think about requests for my time, because every additional yes creates a more constrained schedule.
My current philosophy is similar to Derek Sivers’ idea that something should be either a “hell yes” or a no. Most of the time, it ends up being a no.
I do not think this is necessarily the right approach early in someone’s career. Early on, saying yes to many different experiences can be incredibly valuable. But with time, experience, and introspection, I’ve personally arrived at a place where being more selective creates a better balance and a more meaningful use of time.
Saying no is not easy for me because my natural inclination is to be helpful. But I’ve learned that saying no is often the right decision.
My recommendation for entrepreneurs, especially as they achieve some level of success, is to spend time figuring out what truly gives them energy and fulfillment, and then become much more intentional about saying no to the things that are not the best use of their time.

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