Member-only story

10 questions to ask before going on an entrepreneurial journey of self-employment.

2 min readMar 11, 2025
  1. Am I self-motivated when everything around me is giving signs that it would be easier and less stressful to receive a paycheck in contrast to making one?
  2. Am I able to sustain a decade or longer without attending important family gatherings in order to gain the long-term benefits of independence that come from designing a paycheck, in contrast to receiving the default value of whatever price/rate the boss assigns to the position I work for?
  3. Do I have the emotional stability to take and sustain tremendous amounts of uncertainty, as well as the overall pain of frustration and incompetence of those who do not have the desire to work as long and as hard as I do?
  4. Am I patient enough to be judged and misunderstood by friends and family for an unreasonable amount of time without getting distracted by people-pleasing?
  5. Can I mentally deal with days or weeks with zero results despite my best efforts and highest level of discipline?
  6. Am I naturally intellectually honest with myself internally?
  7. Will I be able to manage the social obligations that come with being independent when no one is telling me I have to do anything at any particular time?
  8. Do I understand the art…

--

--

Steve Douglas
Steve Douglas

Written by Steve Douglas

Steve is a Canadian polymath whose pro music career officially began at age 4 when he performed live @ Wembley Stadium. His focus = tangibly benefiting youth.

No responses yet