I'm Struggling With The World's Worst Boss

“If you have everything under control, you’re not moving fast enough.”

— Mario Andretti

I'm Struggling With The World's Worst Boss

Photo by Gabriel Matula on Unsplash

A close friend is struggling. He's feeling overwhelmed in his job. It's affecting his home life. His boss expects a lot and never gives credit for the little wins. He's expected to work long hours, have perfect execution and know exactly what to do at all times. He feels like he has to say yes to everything that comes across his desk. Do you feel sympathy for what he's going through? Of course you do! You're not a heartless bastard. We can't help but feel compassion for a friend being in a position like this. Here's the problem... we all have a boss like this. The world’s worst boss is you (and me).

As a recent guest on the Tim Ferriss podcast, marketing hall-of-famer Seth Godin did not disappoint. He's damn good at talking in near perfect simplicity about overly complex problems that plague creatives. Godin has worn many hats over the years, but it's his role as a teacher that changed my relationship with business and self in ways I never imagined possible.

One such example is a 2010 blog post titled the world's worst boss. Ferriss gave Godin an opportunity to dive into his thinking behind the memorable piece. Godin said, "Even if you're not self-employed, your boss is you. You manage your career, your day, your responses. You manage how you sell your services and your education and the way you talk to yourself. Odds are, you're doing it poorly."

His words can bludgeon even the most confident of creatives. His simplicity is free from needless ingredients we throw in just so we can swallow an honest truth.

Ferriss and Godin, serial entrepreneurs with some serious street cred, know a thing or two about what it takes to survive and thrive in navigating the obstacles of running a successful business. But here's the part that applies to everyone, your (career/business/life/goals) only grow as much as you do. It's not your external circumstances that are preventing you from moving forward, you are. And it probably has a lot to do with a fear of failure.

Ferriss and Godin have expectations of themselves that far exceed many of us. That they don't like wasting time is an understatement. Yet they both contend with the world's worst boss every day. Their projects fail at a rate that makes most of us feel like a contestant on Fear Factor, living in constant dread of what's next.

I'm the same in that I expect more from myself than a boss would ever dare ask. The idea of extending compassion to myself when I first started a business was non-existent. I had unrealistic expectations and never built in wiggle room for life. I didn't realize that embracing failure is like a bloody superpower. I avoided it like a second helping of broccoli. One serving was enough.

In Tim Ferriss's Tribe of Mentors, author, playwright and overall badass Steven Pressfield gave a poignant answer to the question "What advice would you give to a smart, driven college student about to enter the 'real world?’ What advice should they ignore?"

"Believe me, you've got all the time in the world. You've got ten lifetimes ahead of you. Don't worry about your friend 'beating' you or 'getting somewhere' ahead of you. Get out into the real dirt world and start failing. Why do I say that? Because the goal is to connect with your own self, your own soul. Adversity. Everybody spends their life trying to avoid it. Me too. But the best things that ever happened to me came during the times when the shit hit the fan and I had nothing and nobody to help me. Who are you really? What do you really want? Get out there and fail and find out."

Ferriss, Godin and Pressfield all do the unconventional, they embrace failure. It took awhile for me to understand why, because I was too busy wrestling to hang on for dear life as the emotional rollercoaster screeched around hairpin bends.

Would you expect someone who works for you to be perfect and hold them to near impossibly high standards? If your answer is yes, remind me to never work with you. But how often do you hold yourself to these standards?

The struggle is not talked about nearly enough. A client recently shared a different approach she's taken with running her business Instagram. She felt it had become too curated. It didn't feel like her. She decided to be vulnerable and share her personal struggle. Immediately she received messages of encouragement. I'm so happy you decided to share what you're going through as a business because I'm struggling with all the same stuff. It's refreshing to see an authentic perspective. She came into her own not because she learned a new strategy or business tactic but through her willingness to be vulnerable and show compassion, not just for herself but the countless others who face an uphill battle in doing work that matters.

We can't help but look at people like Ferriss, Godin and Pressfield and assume they never face these challenges. Or that they made it over some hump that dispels any and all future worry in a land of care-free fun. But here's the thing, people who do work that matters will always face uncertainty. You're doing work that puts you in a constant state of challenge. Entrepreneurs seek out problems. Every successful business solves a problem. Which takes a double serving of empathy. If you can't put yourself in the shoes of your customer, you have no right being in business.

People who are driven to grow, both personally and professionally, open themselves to far more opportunities for the impostor syndrome to settle in. The more exposure you have, the less power it carries. It becomes nothing more than background music on an elevator. You know it's there but you can't be bothered to listen. You can become healthier, happier and more productive when you embrace discomfort for the right reasons.

Andrew Garfield talks to Sam Jones about how finding the balance between fear, confidence, and vulnerability is essential to being an actor and artist.

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