Baby Steps, Positivity, and Community: How I overcame Feeling Like a Failure

Treat yourself like someone you are responsible for. I recently heard this on TikTok, yes I know, I sound like such a millennial, but it honestly set a firework off in my head. Often it is easier for me to be kinder to others than myself. I do my best to uplift others but I reserve my harshest criticisms for myself. And no year has that been truer than 2020.

My startup entered 2020 by concluding a round of financing and preparing to scale. We were so pumped about our first marketing campaign utilizing billboards throughout Puebla, Mexico advertising our water and gas delivery service. They went up in late-February. By mid-March, no one was on the road. Our meeting with the largest water company in the country was scheduled the day after the lockdown was declared. We are still waiting for them to reschedule. Our team went remote, I returned to Philly to stay with my Mom. We thought this would only be a couple of weeks but I’m still here, living with my Mom.

The prolonged pandemic shocked the world and our company with it. We pivoted and pivoted again and eventually, the company no longer resembled the one I had moved down to Mexico to grow. Intuitively, I knew this chapter of my life was concluding but I couldn’t accept it. I could not accept that all my hard work was resulting in failure.

As a lawyer, I had experienced stress and anxiety but those are totally different emotions than what I was feeling now. I became nihilistic and depressed (I do not use this word lightly). Fortunately, I was able to come out from the shadows by utilizing: baby steps, changing my self-talk, and soliciting feedback.

I confided to my close friend Max Coyne-Green about my growing hopelessness and feelings of failure. I told him how my productivity ground to a halt and felt everything was pointless. I thought he would encourage me to put my head down and fight through it. Instead, he advised me to take a step back in order to take baby steps forward. Rather than beating myself up each night after failing to be productive that day, he suggested I just try and be productive till noon. The next day I circled the most important things I had neglected and told myself that at noon it would be pencils down. That morning wasn’t easy but I forced myself through it and crossed a few things off my to-do list. First baby step. The next day I increased my workday by an hour. Second baby step. I continued increasing my productivity each day. Soon I was ready to take the training wheels off and continue working even after my stop time arrived. In less than two weeks my baby steps helped me feel like I completed a mile. So where else could I apply Max’s advice?

Instead of actively reading my next self-help book, my next baby step was to listen to a book on tape. Searching on Audible, fittingly, I found Gary John Bishops, Unfu*k Yourself. Bishop claims that to unfu*k yourself, you need to stop speaking negatively about yourself. Instead, use positive, uplifting words in your internal dialogue. A passage that really hit home for me was:

Negative self-talk can not only put us in a bad mood, it can leave us feeling helpless. It can make small problems seem bigger — and even create problems where none existed before. Here’s the breaking news, your self-talk is f*cking you over and in ways you can’t even begin to imagine.”

Immediately I pledged that I would not say anything negative — internally or externally — about myself. No self-deprecating humor. No pity parties. No negativity. Just a baby step forward in how I talk to myself.

With more positivity in my life, I began reading The Miracle Morning by Hal Elrod with the goal of jump starting my day. Towards the end of the book, Elrod encourages you to solicit feedback from others to better understand areas of your life you can improve upon. Elrod even provides a template of an email you can copy and paste. I BCCed 25 people (family, friends, colleagues, and people I look up to) asking each of them to list a couple of things that I need to improve on. Then I took a deep breath. What would they say? What if no one responded? What if no one cared? But they did. Soon the responses rolled in. Some of the responses were a few list items. Others were paragraphs. The length did not matter but the content in each did. I organized the responses into a spreadsheet. Now I had a document for how to become a better version of myself. Mannerism, habits, and suggestions that I needed to eliminate, improve upon, or adopt.

By taking baby steps I was able to move forward without the pressure of competing with my former self. By treating myself with love and respect, I gained back my sense of self-worth. By soliciting feedback I have an increased sense of community and individualized advice to help me grow. This process helped me go from feeling worthless to the best headspace of my life. I am no longer feeling the pressure to compete with my former self as I grow into a better me. If someone you know has experienced “failure”, send this to them. Don’t forget you’re not alone. You have a Max in your corner, you just need to find him or her. And finally, remember, if you’re going through hell, keep going. Thank Winston Churchill for that, not TikTok.

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If you are going through tough times and need someone to talk to feel free to reach out to me at jackbtanenbaum@gmail.com