Lessons Learned From Success

I spent 5 years building a SaaS as an employee, not a founder. It was acquired a few years back. I’ve been trying to write up the good and bad of the experience, and finding it difficult to do so without getting into anecdotes that are more about my own reactions than helpful to other people.

But I did write up some specific lessons learned that might be helpful:

  1. Trust your gut – if a new job doesn’t feel right, it probably isn’t.
  2. Don’t knowingly step into a personality conflict – Dealing with different personalities is hard enough in business and will come along over the course of your work anyway… so there is no need to volunteer for a conflict from day one.
  3. Good leaders are not the same thing as good bosses. If you don’t have a solid relationship with your boss, seek out a new one. That doesn’t have to mean finding a new job – transferring within the company can also improve your working situation.
  4. Companies that feel like family are a double-edged sword – Having a family-like supportive group of people all working together towards a meaningful product is a wonderful experience. Enough so that it makes it easy to fall into the trap of making your self-identity synonymous with your job. This is not wise.
  5. If you feel like your career is stagnating, then it probably is – make an active decision whether or not that is OK with you. There is nothing wrong with staying in a place where you are happy. But if it bothers you, then you aren’t happy. Listen to yourself, and seek out a change.