Ask most entrepreneurs how their business is going and you’ll get a revenue number, a headcount, or some other KPI. Ask them how they’re doing, and the answer I often receive is “fine”. The question I wrestle with is “fine” enough, why not “good” or “great”.
The reason is somewhere in the entrepreneurial grind we feel this lingering question “is this business actually making my life better?”.
Wellbeing research gives us a useful map here. Psychologists distinguish between at least three distinct kinds of wellbeing: hedonic (feeling well); eudaimonic (living well); and, a newer, less familiar addition, psychological richness (living a life of variety, novelty, and perspective-altering experience). Oishi and Westgate (2022), who did much of the foundational work on the third category, argue that a genuinely good life probably needs all three.
I’ve spent the last several months thinking through what each of these looks like in an entrepreneurial life, my own included, and I want to walk through all three here, because I think there is power in recognizing our own definitions of wellbeing.
Hedonic wellbeing: the milestone that never quite lands
Hedonic wellbeing is the most intuitive of the three. Hedonic wellbeing is the feeling-good, moment-to-moment pleasure and satisfaction most of us mean when we say “happiness.” It’s also, for entrepreneurs, the one most likely to betray us.
I was recently meeting with a client who had just hit a substantial new milestone in her business. We talked about giving herself permission to actually celebrate it, to soak in the moment, take the win, give her team a collective pat on the back. Good advice. Advice I am, personally, terrible at taking.
There’s a name for the pattern I fall into, and I’d bet you recognize it too: the hedonic treadmill, where happiness is never a destination, we arrive at, only a pace we keep chasing. Dr. Tal Ben-Shahar calls the specific version of this the “arrival fallacy” which is the false belief that hitting the goal will finally bring lasting happiness. Entrepreneurs are especially susceptible because the same trait that makes us effective, the ability to delay gratification, or skip it altogether, also makes us terrible at stopping to enjoy milestone moments as our ambition moves us mentally to the next task.
Here’s the problem with that instinct: hedonic wellbeing can’t be stored up like grain and sold later. The moment is fleeting. Miss it, and it’s gone, permanently, not on layaway for some future date when you’ve “made it.” So, consider this a field report from someone still in treatment for arrival fallacy: the next time you hit a milestone, actually invest the time to celebrate it. Your employees and your family may need that celebration even more than you do. And for an hour, a day, a week run a self-experiment and see if you can just let yourself be content and soak in the achievement.
Eudaimonic wellbeing: the business that means something
If hedonic wellbeing is about feeling well, eudaimonic wellbeing is a concept that goes all the way back to Aristotle and it is basically living well. It’s less about the high of the win and more about whether the whole enterprise adds up to something that matters.
Many of us build businesses, hit numbers, achieve what looks from the outside like real success yet still feel a void. We ask quietly: what is the purpose of all of this? For some entrepreneurs, Elon Musk being the obvious example, the purpose seems self-evident and drives everything else. But most of us hit an inflection point where the deeper questions surface whether we invited them or not.
I hit that point myself, before we sold Wade Sales and Service. I started pushing our organization to be more impactful at the human level, and it led to something small but meaningful: through our bottled water division, we began delivering free water to any patient undergoing chemotherapy treatment, in honor of one of our founders, Janet Wade, who lost her own battle with cancer. It was a modest financial sacrifice. But being able to show our customers and community that we stood with them gave the work a sense of purpose that no revenue number ever had.
If you find yourself asking “what’s the meaning in this,” give yourself more credit than you probably are. The meaning of your business might be as straightforward as providing employment in a place that wouldn’t otherwise have those jobs, raising the tide for an entire community. Or it might be as simple as treating your customers like people to be served, not resources to be extracted from. When you started your business, you knew your why. It’s entirely possible that why doesn’t need replacing it just needs to be rediscovered.
Psychological richness: the difficulty is the point
The third piece of the picture is the one you’ve probably never heard named, even though you may already be chasing it. Psychological richness, as defined by Oishi and colleagues, is a life characterized by variety, novelty, and perspective-altering experiences. The experiences that create real arousal, in the sense of feeling fully alive, engaged, enthusiastic. And here’s the counterintuitive part: Oishi and Westgate (2022) found that it’s the perception of difficulty, not the outcome, that produces richness. You can fail completely and still walk away psychologically richer for having tried.
I think this is what gets a certain kind of entrepreneur out of bed at 4am, notebook in hand, chasing the next idea, division, product, or customer experience, not the promise of a payoff, but the pull of the difficulty itself. But I’d take the theory one step further: I think the most successful entrepreneurs go looking for psychological richness outside their business too. They do difficult, exciting things that stretch them physically and mentally. The stretching builds skills and resilience that boomerang straight back into their entrepreneurial life.
This one is personal to me. When I signed up for a half Ironman, I was drowning in doubt before I’d even started training. Could I actually put in the work? Did I have the mental and physical endurance to finish? How, exactly, was I going to survive 1.2 miles of open-water swimming? But that fear and doubt turned out to be fuel, the fuel to get up at 4am, do the work, and control what I could control. I didn’t have the language for it at the time, but that was a psychologically rich experience, full stop.
If you find yourself in an entrepreneurial funk, bogged down by the grind and the monotony of it all, it might not be a business problem. It might be a richness deficit. Sign up for a race. Learn to fly a plane. Take the trip that scares you a little. Finally go chase the degree you always thought you didn’t have time for. These experiences aren’t a distraction from the work. They might be the force multiplier you’ve been looking for both professionally and personally.
Putting it together
None of these three, feeling good, living meaningfully, or seeking richness is sufficient on its own, and that’s really the point. A business that only chases the next milestone will burn you out on the treadmill. A business built entirely on meaning, with no room for adventure or difficulty outside it, can start to feel airless. And a life that only chases novelty, with no anchor in purpose, risks becoming scattered rather than rich.
The entrepreneurs I’ve seen build something durable, in their businesses and in themselves, tend to hold all three at once: they let themselves celebrate the win, they stay tethered to why the work matters, and they keep deliberately putting themselves in difficult, unfamiliar situations that have nothing to do with the business at all. That combination, more than any single framework, might be the real definition of an entrepreneurial life worth having and is the basis for my academic research.