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Why Do I Feel Lost When I Need to Move Forward?

As entrepreneurs, we have no existing trail up a mountain to follow. When we feel lost it's because there are large boulders & trees - our own belief systems - that stand in our way.

Woman in black walks past large yellow wall
Photo by Rodion Kutsaev on Unsplash

Earbuds in, I slumped over crying. At 32, I was sitting on the stairs to the basement of my parents’ house desperately searching for a video or podcast that could help me understand why I was feeling lost, anxious and depressed.

Listening to this one podcast, the interviewee, Jerry Colonna, goes on to talk about the journey of the entrepreneur in terms of hiking a mountain. The entrepreneur has no trail to follow. Sometimes the peak is visible and the entrepreneur heads towards it. Other times, the entrepreneur can’t see which way to go. They very well may hack away in one direction for hours, days, or weeks before learning the way they chose was wrong.

On those stairs, I was deep in the woods, I could not see the peak, and the sun was setting quickly. I was finishing my second year self-employed as an independent contractor and I had absolutely no idea what I was doing. After 4 years in NYC, I moved away from the claustrophobia, loneliness and the life-restricting cost-of-living. My plan was to stay a month at my parents’ house in the Philadelphia suburbs for the holidays before heading to Colorado where the fresh air and the snow were waiting.

Yet, life had different plans. The day I was packing my storage unit, my beloved 93-year-old grandfather passed away. Shortly after, my grandmother had a stroke and was put in hospice. My Mom was losing both of her parents and I was losing two grandparents that brought an intense amount of light and joy into my life. 

As the mountain grew dark, I felt successive earthquake tremors. I lost all foundations that provided stability: my apartment, grandparents, social network and a fruitful job market in NYC. The racing thoughts I had did not allow me to enjoy a December off, to mourn or to celebrate any of the accomplishments from the year before.  My thoughts ceaselessly repeated, “You no longer have your own place, you’re jobless, you’re 32 and you’re living at home with your parents.”

The Wolves Howl that You’ll Have No Money

Boulders and trees fell all around me. To the west of me, I could not leave my family. But to the east, moving back to Philadelphia was akin to giving up on my drive to succeed. My younger self always felt a move back to Philly screamed, “You’ll never be good enough and you might as well get used to being ordinary.”

When I looked north, I was blocked by the anxiety and risk associated with my plan. From my desk in Battery Park, I thought giving myself a few months to be a ski bunny up in the mountains while also looking for my next contract was a fabulous gift. Now, I could not stop worrying, “What if no one hires me? What if I run out of money?” 

The Wind Whispers You’ll Never Be Good Enough

To the south, I thought my spirit was too big for Philly. The chip on my shoulder from my childhood, the chip that said I was never good enough, led me to believe my success hinged on being better than my hometown, not in my hometown.

“You could just get a job and see a therapist to cope with working full-time,” my sister said to me. At that moment she didn’t want to see me distressed so she offered me what seemed like an easier solution. 

The keyword “just” screamed to me that I would be compromising on my goals, minimizing my true direction, and setting myself up for another depressive episode. “Why don’t I just sit at a desk?” “Why don’t I just spend my life working on other people’s dreams?” Just be ordinary, just be average, just be happy with the status quo. Just getting a job and just going to therapy sounded absolutely soul-crushing.

I am suffocated and lost when I have not the bright feeling of progression.

Margaret Fuller
Photo by Doug Robichaud on Unsplash

As December moved to January, relationships with extended family crumbled over how to care for my grandmother. “Should I stay or should I go?” I asked over and over again. “Should I camp for the night and wait for the sun to come up? Or should I set out on this other route that seems promising and ominous at the same time?”

After spending a gloomy day in Center City Philly holding back tears for hours while connecting with a friend that came to visit me, a trailhead appeared. My mom’s cousin walked into Rittenhouse Square with her dog. We hugged, she acknowledged my grandparents (her aunt and uncle), and the endless drama from other family members. 

Then she said, “Come live with me in the city.” At that moment, I saw a small clearing and a glimpse of daylight. I found a campsite for the night. Our serendipitous world made the decision for me. “Stay. I will stay…for now.”

Are you feeling lost?

I’m now reading Jerry Colonna’s new book, “Reboot: Leadership and the Art of Growing Up” for the second time. In it, he asks, “Why do I feel lost while I struggle to move forward?” 

My falling boulders and trees represent embedded belief systems (the fear of being ordinary and the anxiety of financial insecurity) that I need to break down almost every time I want to grow. It’s an ongoing process that has led me successfully through 5+ years as a business owner.

How would you answer Jerry’s questions? What are your boulders and trees? How can you get out of your own way?

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