Losing yourself in building an organization

Derrick Duplessy
3 min readFeb 14, 2021

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Why you should care

Do you know a couple who have been in a dysfunctional relationship for 10 years? The kind that love each other but they need some outside help to get all their mess sorted? Well that was me and my life's work for so many years. I had a big intention to change the world but I was just too disorganized to get anyone to follow me long term. This post will share my evolution and the key changes that helped me get clear and get help.

Falling in love with Mission

Walking into the local library I was directed to meet a 23 year old who wanted to turn her documentary photography into a book to sell. We agreed to meet at a coffee shop to discuss her future in business.

"I'm a lesbian" was her opening line. She wanted it out there in case I didn't want to work with her. I was actually more inclined to help her with that kind of honesty.

For the next few years, I taught her what I knew about sales process. She taught me a lot about mentoring, teaching, and coaching. Eventually, she was able to move out of living with family and figure out earning enough with art. Inspired, I took on more artists to teach them sales.

Painful Success

Over the years, lots of cool things happened. Helped launch two million dollar companies. Helped non artistic biz owners grow their sales. I just couldn't bottle up what was successful and apply it to people who had good hearts but no business savvy. The accomplishments felt hollow. My family wanted me to stop. Loved helping folks but I never asked for enough money. I even contemplated jumping in front of the train one night late at the office.

Stumbling into a focus of helping women, immigrants and minorities grow their business gave me motivation to keep going. The results pushed me to read books like Essentialism, 12 Week Year, and 4 Disciplines of Execution. I was starting to figure out what I wanted my organization to become.

Just couldn't get people besides myself to commit long term to building the org that exists somewhere in my brain. Board members, interns, volunteers came and went. Last year, once I got down to one board member besides myself, I knew something had to change.

Getting clear and getting help

Journaling daily and Essentialism got me clear on an event in October to focus on. A sales summit where corporate volunteers work 1 on 1 with diverse business owners on their sales process. 12 Week Year gave me a deadline to execute. The most impactful change by far was deciding to hire my first staff member.

She balanced out my focus on helping others with questions focused on how we were going to help me build an organization. I had to prepare for our weekly meetings with increasingly clearer plans of execution. The cadence of reporting to someone else changed my relationship to the org. I was working for her success and she was working for me.

Tricking my brain to focus on my first staff member quieted the dysfunctional and destructive relationship I had created with my org. I had to become clear with my communication so everyone could do their job. Daily execution no longer relied on me trying to overcome being isolated in my thoughts. Simple follow up questions from her got me out of my trance and focused on "shipping".

The Aftermath

6 months after the first staff hire my org has generated more revenue than ever, we rely on systems, and the relationship between me and the org has slowly become functional. This marriage has a chance to work with more outside help.

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Derrick Duplessy

Founder of Duplessy Foundation - Sales Coaching for Women, Immigrant, and Minority Entrepreneurs