One of the most difficult things I’ve ever done in my life happened on stage at a small conference called Misfit Con in Fargo, North Dakota in May of last year. I was asked to speak about my success as an entrepreneur.

In 2008, I started a unique marketing company called IWearYourShirt, and I’d been running the business for over five years by that time. I’d managed to grow the company from an idea I had while standing in my closet to a business that generated more than $1 million in annual revenue. But, at this particular point in time, I had lost the passion to run my business. Clients weren’t knocking down my door anymore to pay me for my services, and the once rabid community I had built seemed to be getting diluted with the growth of social media networks.

As I sat on stage preparing to speak in front of this small group of passionate creative professionals, a switch went off in my brain. I decided, for the first time in as long as I could remember, that I was going to be vulnerable in front of a group of people. I wasn’t going to regurgitate a story of success and pretend like everything was okay; I was going to be honest.

I don’t remember the details of what I said, but I remember the emotion I felt as the walls I’d built up year after year came tumbling down. At the end of the talk, I was met with a surprising outpouring of support (not just in applause) as people rushed to give me hugs and words of encouragement.

As it turns out, people really respond to the truth. We see story after story of successful acquisitions, IPOs and insert-new-startup-here reaching however-many-million users. But the truth is that business is hard, volatile, and lonely stuff sometimes. When your business doesn’t work out quite the way you thought it would, you’re often left with the frustrating and shameful feeling of being lost.

It took me months after Misfit Con to finally start feeling focused again, but admitting the truth was the first step to finding my way. There were also a few key lessons I learned during that time that helped me pick myself up again.

1. Ask for help.
The first thing I learned is to ask for help. My personal motto in business is “you don’t get what you don’t ask for,” and this still applies when asking peers for help. One of the people that offered me encouragement at Misfit Con was Pamela Slim. Pam was a fellow speaker at the event, and, after hearing my on-stage confession, she told me to reach out to her for coaching help. Unfortunately, it took me eight months to muster up the courage to reach out to Pam because it still felt like admitting defeat. Even though it took longer than it should have, it was one of the best decisions I could have made. Pam helped me finally explore my passions again, find the connective thread in my work and focus my goals moving forward.

2. Identify what’s really important.
Another valuable change following the conference came from the advice I received from yet another speaker named Joshua Fields Millburn (of TheMinimalists.com). Joshua’s story felt similar to mine. He had racked up debt, owned a lot of things he didn’t actually need, and his goals were completely driven by things that society deemed “successful.” While Joshua’s approach to changing his life was a bit more drastic (selling just about all of his things to lead a life of minimalism), he left me with one single question that I ask myself almost daily: Does this thing bring me value? That question not only applies to the things we buy, but also to the work we do and the people we surround ourselves with. I’ve since made a conscious decision to realign my life goals and to think about what brings me value, not what society decides is a mark of success.

3. Remove negativity from your life.
As I realigned my focus during that time, it also became clear to me just how much negativity I was surrounding myself with. My college friends had different priorities in life than I did and didn’t understand the lifestyle of an entrepreneur. Many didn’t actually support my ideas; they just coped with them. Over time, I realized trying to maintain those relationships actually brought me more harm than good.

4. That goes for online negativity too.
I also noticed how much negativity flows through the social networks we subscribe to. My Facebook newsfeed was a breeding ground for complaints, rants, religious/political opinions, and ‘woe-is-me’ status updates. Twitter was riddled with customer service complaints and snarky remarks (while I’m all for snark, too much of it can really impact how you feel). It brought me down so I started intentionally hiding people from my newsfeed who were always negative, unfollowing people who never had anything positive to say, and limiting my overall time spent on social media. By removing negativity offline and online from my life, I was able to feel a huge weight lifted from my shoulders which resulted in clearer thinking for my work.

The path of an entrepreneur isn’t easy. There are times of intense happiness and satisfaction and there are times of struggle and loneliness. Finally admitting that my business didn’t end up the way I planned helped me make major changes in my life that have led me now to a much more balanced way of life and a new excitement for the work that I’m doing.

Published on: Jun 30, 2014
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