Dear Kimberly: The Fear of Failure Is Holding Me Back

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Kimberly McGlonn is back with gentle wisdom to help you navigate life’s tough situations. Have a Q for Kimberly? Fill out the form here and we’ll do our best to feature it in an upcoming column.

Dear Kimberly: I’m in my 30s and have been working on a new business idea that I’m really excited about, but I’m scared to take it further and risk failing in a way that other people will see or talk about. I’m generally a successful person, but at the same time, I feel all this pressure to prove myself, to achieve even more, and to be a successful business owner. You seem like you have everything together. Do you have any tips on managing failure, or at least the fear of it? — Afraid to Flop

Dear Afraid to Flop,

Thank you for that kind assessment, but I’ve got to be clear: No one has it all together — at least not all the time. Sometimes we find ourselves walking through experiments that are actually incredibly lonely, projects that we believe in but where we feel ill-prepared or unsure of how it’s all going to work out. In these moments we often imagine that we’re on this huge stage and that everyone’s watching us, but in reality, people are all on their own stages. In all likelihood, no one else is judging you as harshly or as frequently as you may imagine. And even if they are? Respectfully: So what?

That said, I get that we live in an image-conscious, social media-driven world, where it can feel like people are watching our every move and judging us. To be honest, I think we invite this on ourselves, but that doesn’t make the anxiety that it can produce any easier. It also doesn’t mean you shouldn’t shoot your shot.

Almost a decade ago, I launched my first business in this high-visibility climate. For eight years, I ran a fashion company called Grant Blvd, which included online and brick-and-mortar stores in West Philly. To your point about image, I’m often told that on the outside, it looked like everything was a-ok – but what no one could possibly know was that, in addition to all the joys and highs and success of feeling that I was leading a business that aligned with my values, I was faced with a series of what felt like “micro-failures”: an investor not coming through, a collection not taking off with our customers, math just not math-ing when it came to overhead. But I have no regrets about trying, and doing all of that in public. No, things didn’t always go the way my team had hoped, but I learned so much from the experience and the people who that effort led me to.

Failure — even the possibility of it — can paralyze us from trying. It brings up irrational fears of embarrassment and regret. But once you try something, you’re always gonna be learning more about what to do next and how to move forward. Staying still (not trying at all) doesn’t move us forward — putting one foot forward, one step at a time, does. If we only focus on what didn’t work out and all the losses, then we don’t see the lessons. It’s like Nelson Mandela once said: “I never lose. I either win or learn.”

Many of us are conditioned to think that we have to move through life in huge leaps, but sometimes, it’s the baby steps that add up. Are you scared to launch your new venture because you don’t want to give up a secure paycheck and health insurance? That’s a rational concern. Perhaps you can instead dip your toe into your business as a side hustle while you research alternative income streams and affordable insurance options. Are you scared to take out a loan and be beholden to the pressures of another monthly payment? Maybe you can investigate grant opportunities or reach out to your social network for smaller investments of support. Do you feel like you just don’t know enough? Maybe you can take a local or online class to fill the gaps in your knowledge. None of us know what we don’t know, but asking questions is one way to start answering the questions we don’t even know we have.

I’ll never forget the day I closed my store on 34th and Walnut. It felt like going to a wake for a creative baby I had dreamed up and nurtured and birthed into the world. On that last day, people who had been with me on the journey for the previous eight years showed up to sit with me as we collectively mourned what was ultimately a failure of our economy, of our culture, of the moment. Somehow, I lasted the entire day with no tears. I was emotionally composed, and found myself trying to make space for other people’s emotions as they expressed to me their gratitude, or their disappointment that it was closing, or their sadness that it hadn’t worked out differently.

Then, at the end of that day, a woman who understood just how hard I had fought, Tess Hart of Triple Bottom Brewing, appeared. I knew she understood how hard I’d been working, and what it was like to sit on the precipice of saying I couldn’t do it anymore, and that was when the floodgates opened.

As we face moments of change in the face of unlikely odds, we have to make sure we surround ourselves with people who have the capacity to hold us when we are afraid or when we may feel like everything is lost. We also need to be there for people and be in a lasting community, helping others when they need us and leaning on them in our moments of need, too.

Work to preserve the relationships with people who are rooting for you. There will be moments of disappointment and frustration and learning as you seek to launch this new venture. But there will always be an opportunity to honor what you pursued and to celebrate the lessons that are unique to your story of trying. And regardless of the outcome, it will all be really rich soil for whatever you choose to plant next.

With courage and care,
Kimberly