Why Do You Work?

“an illustration of a mountain made up of many layers in the style of roy lichtenstein” | Midjourney

I visualize my relationship with success a lot like the image of the mountain above.

I can see the layers of experiences, beliefs, and stories that, over the course of my life, constructed the mountain of greatness I endlessly climbed.

The foundational layers were laid as a kid when success was the currency through which I earned love. It wasn’t that I wasn’t loved if I failed. My parents loved me no matter what. The love just felt better when I succeeded. It was brighter. Warmer. I was told I was special, and I believed it.

The next layers formed as a teenager when success became how (I thought) I could earn acceptance. I didn’t think my personality would earn me the belonging I craved, so I tried to “win” respect by being good at sports, school, video games, wherever I could find a competition to conquer. Of course, the foundational layers of love and admiration I received from parents, teachers, coaches, and gaming fans continued to glow brightly as my mountain of success grew taller.

The top layers formed as a young adult, when success became a path to the financial freedom I’ve always yearned for myself and my family. The belief that I was “special” still deeply rooted, I bypassed the traditional career path and dove head first into startups and entrepreneurship. To this day, I’ve still never interviewed for a job. Social media was growing rapidly and I was a natural at it. The first two layers of my mountain continued to glow bright, and I earned love, attention, and admiration at incredible scale.

Work became my life. It became my identity. If I wasn’t working, I was thinking about work, or numbing myself enough that I could actually give my brain a rest. My company was my “baby”. I was my company.

I worked to feel like I was worthy of love, acceptance, and security. Of course, rooted in that story was the belief that I wasn’t already worthy of those things and that external success was the solution.

This brought me a great deal of angst. My well-being ebbed and flowed with my perceived success. If I did well, life was good for a moment, but I’d be waiting for the other shoe to drop. If I wasn’t doing well, life was bad, and I was convinced that I just didn’t have what it takes.

Anxiety was ever-present. Depression a regular visitor. And a dark hole of emptiness grew and grew until, eventually, I lost all motivation, all passion, and found myself “hollowed out”.

Look, it wasn’t all bad. I built great things. I helped thousands of people, and positively impacted millions. There were points where I had a lot of fun and got to work alongside incredible humans. That was there too. But the undercurrent of “not-enoughness” was too strong. No matter how hard I swam, I drifted ever closer to the abyss.

The last two years has been a process of excavating the layers of my mountain of success.

As I dug, the layers revealed themselves. I became familiar with the stories that have been fueling me. The belief that I needed to succeed in order to be worthy of love, acceptance, and security. The “lack” that drove me to work so hard.

I dug, and dug, and dug, with the support of my “excavation crew” of teachers, guides, coaches, friends, family, and therapists until I reached the core of my mountain. And at the core, I discovered the truth:

I am already enough. I don’t have to work for enoughness. It’s always been there, inside me.

This was an earth-shaking realization.

Slowly, as I let go of the idea that I have to earn my worth, success’ grip on me loosened and my reason for working began to shift.

This led to a period of time where I lost all motivation. No longer driven by not-enoughness, I couldn’t find a reason to work. The “chip on my shoulder” was gone. My “dirty fuel” emptied.

If you’re already enough, what’s the point of working?

Slowly, the universe started to bring me the answer.

Opportunities for work started to come to me. It started small. A book to read. An article to write. A request for a conversation.

With each opportunity, I had a choice. Do I say yes? Or do I say no?

I knew what my criteria would have been before: Does this work make me feel like I’m enough?

This time around, my criteria was different: Does this work give me life?

If the task made me feel alive, if it gave me a feeling of expansion, I would say yes. If it felt like it was taking life out of me, if I felt a sensation of contraction, I would say no.

Eventually I did a values exercise, the same one we do with our clients at Downshift, and it helped me bring more clarity to what gives me life today.

I landed on four which I keep on a note on my desk at all times:

• Connection: I want deeper contact with other humans and

  beings on this planet. Whatever I do, I want it to bring depth of connection.

• Joy: Whatever I do, I want it to bring me joy. I should feel the energy in my body rise as I consider investing my gifts. I want to have fun.

• Health: I want to be alive and capable as my kids grow old. I want to wake up feeling strong and energized.

• Security: I want to provide for my family and my community. Whatever I do, I want to make sure that our basic needs are taken care of.

So as I was presented with work to do, I could feel into my body if it made me feel alive, and I can run it through these values to make sure it aligned with at least one of them, and didn’t conflict with any of them.

I said yes to the work that was aligned. I read that book. I wrote that article. I took that call. I did that again and again and again until I looked around one day and realized that I’m working full time again.

I’m now fully “upshifted”. I’m busy. I’m working five days a week. I’m hustling.

But this time around, work has felt entirely different. My work is much less driven by the “lack” of my ego. It’s much more driven by a yearning to live fully and be of service.

I notice that I no longer need external measures to tell me that I’m on the right path. I used to need to measure everything, and compare it to others. Now, I can just feel it. I know in my body and my heart when I’m in alignment. My mind, heart, and body are my compass. I trust that it will lead to the outcomes I need to be okay.

Of course, old patterns still show up. I am not a “fully integrated being”.

I still have fears of loss of love, of abandonment, and of financial ruin if I fail. Not-enoughness still rears its head on multiple occasions every day.

My practice now, when those parts arise within me, is to notice them, acknowledge them, listen to them, and thank them for the ways they’re trying to serve me. Usually, when they feel heard, they soften back. As a result, I don’t get as lost in them as I used to. I can then tune back into that steady sense of being enough sitting at the core of my mountain, and work from that place.

This practice brings me a kind of confidence, a fearlessness that allows me to keep moving forward. No external setback can take away my enoughness—it’s something that’s mine, unconditionally.

If I could go back and speak to my younger self, who was working so hard to become enough through work and success, I’d tell him that the goal isn’t to eradicate his pain by throwing himself into his work, but to lean into his suffering and let it be his teacher. Eventually, he’ll learn to love the parts he’s most ashamed of. I’d remind him that he’s already enough, already whole, just as he is.

So, why do I work? At the end of the day, it all comes down to this:

I work to give myself life and be of service during the short time I’m on this beautiful green emerald soaring through space.

Why do you work?