Entrepreneurs are often told to work hard. Less often are they reminded to play hard, not as an escape from the work, but as part of the life they are trying to build.
On The Complete Entrepreneur, hosts Colin C. Campbell and Michael Gilmour explored that tension in a conversation about energy, ambition, family, rewards and the strange reality that, for many entrepreneurs, work does not always feel like work.
“Nothing existed without the work of an entrepreneur”
“For me, I view my business as basically an amazing game,” Gilmour said. “There’s no computer game in the world like my business.”
That idea became one of the central themes of the discussion. Entrepreneurship is not a tidy nine-to-five existence. It often spills into evenings, weekends and vacations. Campbell noted that when a major deal is on the table, “there is no such thing as evenings and weekends.” The work must get done.
But the question is not simply whether entrepreneurs should work hard. They already do. The deeper question is how they can build a life that does not collapse under the weight of their ambition.
Gilmour argued that entrepreneurs are, by nature, unbalanced people. They are the “tip of the spear,” the ones pushing society forward by creating new products, new companies and new possibilities. “Nothing existed without the work of an entrepreneur,” he said. “Someone, some entrepreneur somewhere said, I think I can build a better world.”
Campbell pushed back slightly, not against the intensity itself, but against letting it consume everything. He described entrepreneurship as more organic than balanced. He may work late at night on a new venture, then spend the middle of a weekday playing cards with family. That flexibility is one of the gifts of entrepreneurship, but it also requires rituals that signal when work is over.
For Campbell, that ritual might be the hot tub. For Gilmour, it was once putting on moccasins at home, a signal to his family that “Dad’s at home.” These small transitions matter because entrepreneurs rarely switch off naturally.
Guest Jason Kinte added another important layer: life stage matters. A young founder may be able to work around the clock with few responsibilities. But someone trying to build a family may want more stability, more structure and the ability to go on a date or honeymoon without worrying whether a deal has closed.
That does not mean ambition disappears. It means the business must fit the season of life.
One of the strongest ideas from the conversation was that entrepreneurs should design their companies around the life they want. Gilmour chose to build a work-from-home business when his children were young. Campbell has leaned into ventures connected to his passions, including dogs and life at sea. Kinte spoke about wanting control rather than being driven by investors.
The point is not to avoid hard work. It is to make sure the work serves a larger purpose.
Celebration was another recurring theme. Campbell warned younger entrepreneurs against waiting too long to enjoy the journey. Do not wait for the final exit, the huge valuation or the perfect moment. Celebrate the first distributor, the first product launch, the first meaningful win.
Gilmour agreed, admitting that he often struggles with this himself. “You have to reward yourself as an entrepreneur,” he said. Rewards can be large, like a long-awaited trip or conference, or small, like great seats at a show, a family outing or even paying for a stranger’s groceries after a good week.
In the end, “work hard, play hard” is not about reckless hustle followed by reckless indulgence. It is about building a life where work, creativity, family, rest and reward are not enemies.
For entrepreneurs, the work may always be intense. The challenge is to make sure the life around it is rich enough to be worth the effort.
