Why Do I Feel Guilty and Inadequate About My “New Rich” Life?

“Develop the strength to do bold things, not the strength to suffer.” — Machiavelli

For years, I have driven up and down Coast Highway as part of my daily commute… and for years, I have been jealous of the people I would see jogging 🏃🏻‍, biking 🚴🏼‍ and surfing 🏄🏻‍ while I was sitting in gridlock, drinking cold coffee and dreading the day ahead of me.

When I made the choice to leave my full time job and build my own event management company, I promised myself that I would become one of “those” people enjoying the benefits of a Southern California lifestyle (it was time to take some benefit from the sunshine tax!). And for the most part, I have stayed true to this with a.m. jogs along the coast.

Morning Jog on the Beach in Encinitas

But somehow, I still feel shackled… Instead of enjoying my new found freedom of time and mobility, I feel guilty. I feel like I am doing something wrong. I feel like I should be back in the car commuting somewhere.

“Most people will choose unhappiness over uncertainty…” — Tim Ferriss

On an intellectual level, I know that returning to a 9 to 5 is a dead end. It is not what I want for myself and is a step in the wrong direction. A J.O.B means my income potential is capped and I would be giving up the flexibility of time and mobility… but still… the myth of stability calls me… The false construct of busy = productive continues to play tricks with my head.

“Being busy is most often used as a guise for avoiding the few critically important but uncomfortable actions… Being busy is a form of laziness- lazy thinking and indiscriminate action.” — Tim Ferriss

Even after my awakening I find artificial comfort in work for work’s sake. I know though, that I am doing what I want and what is best for my family. I am building a company that is inherently valuable and delivers on my unique talents and interests.

“There is more to life than increasing its speed.” — Gandhi

I have exited the rat race, removed the non- profitable elements of the daily routine and am spending more and better time with the people who are important. Maybe most significantly, I am finding myself again.

Despite this… feelings of inadequacy pop up and a sense of panic rushes in on an almost daily basis. I am proud of the choices I have made and the progress I am making, but still feel like I need to qualify or downplay my entrepreneurial ambition when talking about it with others.

I guess this is both the engine that drives entrepreneurism and the tether that restricts it.

After the first quarter of operating Stylehawk Event Services on a full time basis, I have some reason for optimism.

  • My business model is built on repeat and referral business. That is holding true so far. All of my clients have booked multiple events through me and my venue partners are creating referral opportunities.
  • I have been able to significantly increase the quantity of venue partners in the Stylehawk Venue Directory with diverse and engaged sport event venues.
  • I have established a number of new strategic partnerships to amplify our service offerings. Production partners, hotel sourcing partners, ticketing platforms and drone photography are new elements in the marketplace.
  • I have created a ton of new educational content and have developed a publication schedule to improve search engine rankings but more importantly to establish myself as a thought leader in the event and venue management industry.

I learned from Grant Cardone in The 10x Rule, that the thrust of my attention as a small business owner needs to be on customer acquisition. In concentrating on this element of business development, I have quickly become passionate about content marketing. It may go back to my experience on a college campus and accepting my role as an educator… I love the idea of creating content that educates my client base and strategic partners. That I can share information that is helpful. That my business is authentic and fills a need. I also happen to enjoy the writing process. It has been really cool that the pursuit of one passion has led to the discovery of another passion and that both contribute to the growth of Stylehawk.

Progress… Stylehawk is taking shape in ways that are different than I envisioned and this is exciting. I see it growing as a virtual venue management platform and as a marketing vehicle. I have developed tremendous admiration for different venue types and venue management structures. I am inspired by the generosity and entrepreneurial spirit of the service providers I am working with. I am challenged by the new skills and educational material I am learning to grow my business and I am thankful for my past experiences that have led me to where I am. I also hope that I am a better father, husband, son and friend now that I have had the opportunity to reprioritize. Progress…

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