I plan to leave my job in 2023 and move into entrepreneurship/coaching (I’m currently getting certified thru LCS).

I have had a goal of moving back into entrepreneurship for several years (I was previously a solopreneur before moving into this corporate role about 12 years ago)…. But….lately, I find myself second-guessing my decision. My question is about what is really behind me second-guessing.

If it is about fear…..I get that, because as much as I do want to leave my role, there is also a part of me that thinks, “Are you crazy? You have such a great job… why would you leave? A recession is coming, it’s a terrible time to do this… You’re already 50, you’re too old to start a new venture, etc etc” So those voices are loud, no question about it. I have done (and need to continue to do) models & coaching to look at these.

Recently, the CEO of our company approached me about staying on after 2023 & taking on a bigger role. Normally, I would think, “Thank you, but no… I am going to leave at the end of 2023 when my contract is up for renegotiation…” Part of me is still of that mindset.

However, through Scholars, etc., I’ve also begun to see how I have a pattern of avoiding certain challenging situations (i.e., I skip a work dinner because I don’t want to ‘deal’ with some of the difficult people attending… I feel frustrated in certain meetings because I struggle to find my leadership voice… (PS – I lead a big part of this company right now, which is ironic…)

I thought I had made a very clear decision: “I am leaving after 2023.” Lately, it just doesn’t feel as clear to me. Is it because I’m afraid, or am I just hitting a wall with certain behaviors of mine at work?