Success is a Feeling, Not a Destination

And how your feelings can guide you on the windy path to being “enough”

“What we strive for in perfection is not what turns us into the lit angel we desire.” — David Whyte

Success. It’s this illusory thing we all seem to be striving for, but how do we know it when we’ve reached it or become it?

I was talking with an entrepreneur at an event recently about his goals and dreams for his current venture and his life. As we chatted about his vision and values, a string of his words made me pause. And deeply ponder.

“Once I am successful,” he said, “I will be worthy enough to have the kind of mentor I want and need.”

From my perspective, he was by every measure a self-made entrepreneurial “success”. He had gone through several successful exits, created multiple thriving businesses (including his current venture) and a long history of proving he had the talent, grit and resilience to find a solution to a problem, bring an idea to life and develop it into something truly exceptional.

“So how do you define success?” I asked. “And how will you know when you’re successful?”

He paused. He thought. He explained that he wasn’t sure he knew other than it probably correlated with his earning status (in the millionaire/billionaire realm) and possibly included being on the cover of a business magazine.

“And that’s what would make you worthy of the mentorship you want?” I asked. “Or the life you want?”

“YES.”

That part he was sure of.

How do we define success?

My conversation that night really struck me and led me to reflect on many levels. First, I wondered how I would have answered my own question and if I truly knew my own definition of what would constitute a successful life. Of course I also had ideas that clearly fit into my version of the success bucket, but the edges of that container were still a bit blurry and indistinct.

Second, I wondered how many others of us were out there, the doers and dreamers putting our heads down to forge ahead with the next idea and toward the next iteration of life, one that would lead us to achieve this amorphous thing that could somehow make us “worthy”. And if our worthiness depends on achieving a version of success that we aren’t truly able to define, then how will we ever be ENOUGH? Let alone be successful?

Enough already.

The trap of “not enough” is one of the most common of self-sabotaging beliefs among the entrepreneurs I work with, myself included. It often starts with my thoughts the moment I wake up tired: I didn’t get enough sleep. Or the other version when I’m well rested: I didn’t wake up early enough.

Then there is the cascade of thoughts throughout the day: There is not enough time. I don’t have enough money for that. I didn’t produce enough today or finish enough on my to-do list. I didn’t say enough in that meeting. I haven’t thought this through enough.

The list goes on and on, day after day, each disparate idea adding up to the exact same conclusion: I am not enough.

While there are psychological tricks to practice our way out of that trap, starting with how we engage with our inner critic (or what I like to call my mental “shitty committee”), this conversation made me realize that there is another route to finding “enoughness”: getting crystal clear on a definition of success. Because if we can’t clearly define success for ourselves and fully feel the truth of it in our own mind and heart, then society, family, colleagues, marketers or {insert just about anything else here} will define it for us. And generally those definitions are unattainable by most (starting with the six-pack abs and ending with the billionaire status) each designed to make us buy into an accepted illusion of success that’s not realistic and likely won’t match what’s truly meaningful and important to us as individuals.

Now I’m certainly not saying it’s wrong to want to be part of the billionaire club. (But personally, I’ve stopped caring about the abs). What IS clear is that if we don’t know where our “successful” destination lies, we will never, ever reach it.

The essence of success is a feeling.

When I started my organic prepared meal delivery business in 2009, I wasn’t chasing success necessarily. I was heeding my entrepreneurial calling because I saw a need in my community and I wanted to help meet it. Mainly I saw entrepreneurship as a path to freedom, a pursuit that would allow me to make my own schedule, be my own boss and fully own my life choices. It was that feeling of being free that I was really after.

By many measures my company was successful and by default you could say that I was successful too. The problem was, the type of business I built never really allowed me to have that free feeling. Food production and delivery was grueling work and often complete operational chaos, my commercial kitchen and cafe was open six days a week, I was managing 20 employees, I typically worked 12–14 hours a day, and commonly I was equal parts CEO and equal parts plumber/wearer of every other imaginable unglamorous hat. For the first five years, any “vacation” I took simply meant I worked a mere 6–8 hours a day but in a different location. Even when my company was more stable and my life was more balanced, the business I had built never quite fit me. I couldn’t shake the feeling of the weight of it and the many ways it tied me down in my life.

Years later, after selling that businesses and starting a new one, and after many conversations with both aspiring and highly effective entrepreneurs, I’m beginning to truly understand the foundational place our desired feelings should take in any goal we are chasing or in any definition of personal success. It’s what author and teacher Danielle LaPorte calls “goals with soul,” or where your intense striving meets absolute alignment with the essence of your spirit. As she says, “You’re not chasing the goal itself, you’re chasing the feelings that you hope attaining those goals will give you.

So, if we don’t get to feel the way we want, achieving the “thing” or getting to a certain “place” will ultimately be unfulfilling and misaligned.


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While this isn’t an entirely new reflection for me, I’m grateful that this recent conversation reminded me of this important lesson, especially during a stretch when my internal “not enough” saboteur has been especially vocal (you happen to know that voice too??). And since I’m in the habit of taking these things I notice and actively integrating a way to engage with what I’m learning — so maybe I can help you do the same — here are three things I’m personally practicing:

#1. I’ve recommitted to actively cultivating the ways of being that make me feel my best — when I’m healthy, curious, creative, playful and connected to myself and others — and intentionally evaluating the projects, people, and personal practices I choose to engage with (or not) through that lens. Reminders are super helpful too (think: sticky notes, daily mantras, phone reminders, drawing on the bathroom mirror. Whatever floats your feelings-driven boat).

#2. I’m working on telling my shitty committee, “Hey, thanks for sharing! Now take an effing hike.” That one’s pretty self-explanatory. And feels pretty damn good too.

#3. Most importantly, I’m reminding myself daily that if I succeed at feeling the way I want to feel more often than not, that I’m moving my life’s most significant barometer of success in the right direction. And THAT is enough.

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What will you do today to cultivate how you want to feel? What rituals can you create to support the development of those feelings in your business and your life?

I’m curious how the evolution of that inquiry may shape or reshape your own definition of success. And whatever that definition is, I hope it gives you all the feels you want.