8 things I wish I’d known before working at my first startup.

Six years ago I was ready for a different work experience. My resume was chock full of traditional administrative positions that paid the bills but held little interest or excitement. After years of managing books and executing other people’s ideas with which I felt no affinity, I was ready for a shift.

I wanted to be deeply connected to my work, work with a product I felt invigorated by, and to be a part of the bustling startup community I had fallen in lust with from my internet spectator seat.

When I was lucky enough to land an interview for a role that fit my-work-at-a-startup objective, I allowed my excitement, assumed good fortune, and some deep rooted personal issues to distract me from taking the time to reflect on if the job was a fit for me. …

To practice self-inquiry is to experience and move through discomfort.

Sometimes the work to a whole life feels limitless and broad. An ever-expanding field of opportunity ripe for exploration.

Sometimes the work feels raw and vulnerable. Petrifying, aggravating and overwhelming.

I’ve been cultivating a practice of self-examination for over eight years. I am committed to a life-long process.

But today — today I wish I could just graduate already.

A few weeks ago, the fruit of all my self-work was to bear witness to a dysfunctional pattern in myself and my family. The first taste was exhilarating, exciting. More to learn. Potential for change and growth. …

Less hustle. More authenticity.

Less strategy. More purpose.

Less hours. More efficiency.

Less outcomes. More experiments.

Less secrets. More transparency.

Less instructions. More understanding.

Less happy. More whole.

Less fear. More inquiry.

Less politics. More productivity.

Less culture fit. More conscious conflict.

Less people performance metrics. More vulnerability.

Less diversity. More inclusion.

Less us and them. More empathy.

Less management. More Leadership.

Sensitivity is a virtue, not a disgrace.

I was seated across from my new boss, just 90 days into my new role overseeing operations and community for a professional network. I was trying my best to follow proper managing up techniques to express that I was feeling the crush of an Everest of work on my plate. It was just too much to expect one person to do. Pomodoro technique, reprioritization after reprioritization, logging hours on weeknights and weekends — nothing was moving the needle toward a place where I felt the role would be sustainable.

I had found long ago that it’s best for me to come into anything remotely resembling confrontation with a clear plan. And I had mine. On a four by six notecard was a clear definition of what I believed to be the problem alongside potential solutions listed tidily in descending order of preference. Grow the team and split the role. Recruit an intern. Reduce the scope of work for the next six months to better suit the capacity of our small team. Move tasks from my plate to his. And least of my favorite, but a realistic option nonetheless: admit I wasn’t the person for the role after all. …

Finding the service in going first

A year and a half ago I dove back into the pool following a twelve year absence. My formative years had been filled with swim meets, practices and awkward poolside team photos. Once my hips arrived in my mid-teens, I simply was no longer fast enough to be a real competitor and stopped practicing. I set swimming aside and only missed it occasionally, often when wafts of chlorine made their way down a hotel hallway on a work trip.

Following the birth of my son, my now preferred exercise of running felt cumbersome and hard with my changed body. Our fancy new gym had a pool (and excellent childcare!) and offered Intro to Masters and Masters classes. Masters is a nationwide organization that in a nutshell is swim team for adults. Despite being terribly intimidated by the standards for athletics in Boulder, I started attending the Intros classes and fell in love with swimming all over again. …

It’s not just founders struggling with burnout, depression or mental health at startups. I should know. It happened to me.

My startup story starts in Loveland, Colorado. I had shimmed my degree in electronic media into a project management position at a fast-growing, then fast-failing company. Founded by a dot com success story, the company sold educational resources to aspiring entrepreneurs.

It was my first taste of the entrepreneurial adventure. I loved the fast pace, experimental nature and rollercoaster descents of fast success. My years there were also littered with dysfunction (a fair share my own), poor leadership and management. Eventually that company’s growth bubble burst and I was laid off alongside a large number of colleagues.

It was during that role that I first learned of the burgeoning Boulder startup scene. I cultivated an obsession over startuppers’ Twitter feeds, devoured episodes of Techstars’ “The Founders” and I was soon making regular trips to attend Ignites, meetups, and the first Boulder Startup Week. …

Know That You Are Not Alone

Depression lies. It tells us that we are the only person who has felt loss, who has felt failure, who has felt desperation, who has felt nothing. This simply is not true.

There are litanies of other people who have felt this way. And progressively more and more people in the startup community are opening up to share their personal experiences every day. Brad Feld, Tim Ferris, Ben Huh, Jason Calacanis, Rand Fishkin, Andy Sparks, and many more have shared their experiences.

Connect

It is one thing to intellectually know that you are not alone. It is another to feel it in your heart. When we open our heart and mouth to share with another, we move and transform energy. …