Despite a deep history of success at companies I’ve started or joined, I find myself struggling with imposter syndrome.

I’ve recently embarked on an incredibly challenging adventure where I slowly grow an executive consultant business. At the same time, simultaneously launch a SaaS (software as a service) company focused on marina management software.

By any measure, things are going well. I should have nothing to complain about nor doubt at this point. I’ve been at this for a year and a half. Yet, some days I honestly feel like I’m playing pretend and have no idea what I am doing.

I know it is an irrational fear. I know this is an incredibly familiar feeling to many. Including individuals who are orders of magnitude more successful than anything I’ve accomplished. I also know my career to date is not a giant accident or coincidence. For my new SaaS company, I have multiple customers already. They have signed contracts and are eagerly waiting for the software. So it is not “made up”.

Yet, here I sit, feeling like a giant phony and everyone is going to see me for what I am a phony.

I’ve noticed these emotions and irrational thoughts spike at times of unanticipated execution stress. For example, I spent the last three days fist fighting with the following.

  • PostgresSQL suddenly stopped working on my work machine. It took a day to troubleshoot and resolve.
  • Webpacker, by default, has issues running on Heroku with Rails6 and is a nightmare to troubleshoot.
  • Capybara is having trouble interacting with a Bootstrap plugin I’m using. I need this plugin as its UX is…. perfect. I also need integration tests … so insert unanticipated execution time.

None of this is out of the ordinary; however, it has put me behind schedule. Being behind schedule makes me feel like I don’t know what I’m doing. Ergo, I must be a giant fake, and my entire career has been a sequence of fate mixed with luck, and now the whole world will know.

Bonkers how my brain works sometimes. At least I know the fears and anxiety are irrational.