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Feedback and support

Now that I have a half-year of successful self-employment behind me, here is a look at what it would take for me to look back.

Chance Strickland headshot

Chance Strickland

December 18, 2018 ·2 min read ·


I had the opportunity to receive feedback from one of my team leads yesterday. It was insightful and helpful as it usually is when I get good, thoughtful feedback (something that is rarely offered unless explicitly requested, it seems). During this discussion he and I discussed my status as a contractor and some hypothetical scenarios under which I might consider full-time employment with the company. I won’t divulge details of the conversation, but it was a good question that made me think about what it would take to draw me back into a 9-5 role.

Since leaving my last job six months ago, I’ve been given more offers than I can remember ever receiving during times where I was actively looking for work. It’s been a flattering and humble experience to be sure. But the primary reason I’ve turned them all down is because six months ago, I decided to bet on myself. For the first time in a big way, I wanted to trust that I could carve my own path, and six months is hardly a long enough period for me to gage the results of this experiment and turn back.

But is entrepreneurship my end goal? Would I ever give up and go back to working for the man? Perhaps! There are certainly tradeoffs and aspects that I miss. Ultimately the choice will come down to a few key questions that I’ll need to answer for myself about the opportunity in front of me. I derived these questions from the core values I hold close and consider any deviation from those values to be a non-starter.

  1. Does the opportunity provide me with a path towards my professional goals?
  2. Do I initially trust the person who would be directed with overseeing this path forward, and is there an accountability structure in place to measure progress and advancement?
  3. Does the opportunity provide the freedom and flexibility I need to live the life I want to live outside of work?
  4. Does the culture promote constructive two-way feedback, and is feedback provided to leadership truly welcomed and taken seriously?

This last question has become, perhaps, the most important in my mind. In my experience, a company’s culture can be made or broken by how bottom-up feedback is facilitated. Consider this all-to-familiar directive:

Well, this is clearly not the right way to do X. But [insert CEO/CTO name here] asks for this and so that’s how we have to do it. Too many team leads at too many companies

Red flag. Approach with caution.

Sometimes this is the manager’s failure; maybe not pushing back is just easier. Sometimes it’s just not a big issue and, well, we all have to pick our battles. But more often I believe it’s because the CEO/CTO in question has indicated, either directly or indirectly, that alternative opinions and feedback are not welcome, so the manager reverts to self-preservation mode. And if the executive team does not trust the folks they hire to bring valuable perspective and insight to key decisions, this is a deep cultural problem that is much, much more difficult to overcome.

If I do decide to dip my toes back in the water of employment, I expect hiring managers to have a good answer to this question.