Struggling to make a decision


For almost 10 years, I’ve worked at a specialized consulting firm – we coach and advise CEOs at big companies and their teams. I lead our consulting practice. About six months ago, we were acquired by a much larger company. The acquisition was a surprise to me….but the timing was good in some ways, because I had been planning to leave my job. Previously, I was an entrepreneur (coaching + training inside companies) and was ready to go back out on my own coaching and doing more personal/life coaching work with clients. I was ready for a change, to go back to being an entrepreneur. I am not a life coach but was exploring getting certified for this reason.

Long story longer… When I resigned, my CEO approached me and asked me to stay on for 1 year. She offered me a retention bonus to do so – this also included me renegotiating my contract with the bigger company that acquired us (I had a pretty brutal non-compete agreement initially) – so that helped. In my mind, the thought was: “OK, I’ll stay on for another year and get rid of my non-compete agreement…I’ll take the bonus at the end of the year, and I’ll go.” The bonus is not nothing, but it certainly isn’t something huge (about $100K)

So, we’re getting towards the halfway mark of my year and my CEO approaches me again. She says: “I know you want to leave. I will write you into our earn out …. so, you’ll get a substantial payout if you are willing to stay for about 2.5 more years.” She knows I want to leave to go out on my own and is supportive. Her point to me – “Stay… and then take the money after 2.5 years and use this to fund your dream.” The earn out is a much bigger payment that a few of us get if we hit certain numbers, profitability targets, etc. So the earn out is not a guarantee…. but it is likely because we are hugely incented to make this happen.

So, I am struggling to make this decision. I am already contracted to stay in my job leading the team until April 2022. If I take her offer, I’m in the role until about 2024.

A few other points: I am about to turn 50. That is not insignificant… part of me thinks, “You are running out of time!!” And, I don’t know exactly how much money we are talking about when we say “you are part of the earn out.” So, I need to find that out. I like my job and also would love to go out on my own…. I believe that ultimately, I would make more money on my own, but I currently earn around $350 – $400K a year. The acquisition is a roller coaster – I am in a ton of meetings, on calls constantly. I am married, two kids. There are pockets here and there in my week and on weekends to do “personal work” – which I take advantage of, but doing a major side hustle with this job is challenging given the schedule and the demands of the job.

Here’s the other thing: I was an entrepreneur before, in my early 30s – I had a 3-year-old and newborn at that time. As an entrepreneur, I did…OK. Some big wins. Got a book deal & a few big clients. AND – it was hard. Some big losses. Total emotional roller coaster. Wish I had Brooke’s wisdom at that time 🙂 So no question, part of my brain is telling me: “Remember last time and how tough it was? Do you really want to go back and do that again?” I should also say: In my current job – I coach, I work with clients, and I have to sell. I have been the top seller at our firm for almost 10 years…so that’s a big reason why my CEO doesn’t want me to go.

I was talking with my husband. His advice: Just do the math on this. Figure out how much you’d need to get in the earn out for this to make financial sense. For instance – if they offer you $4M to stay 2 years, do it. If they offer you $10K to stay, don’t. Figure out what the right $ amount is. That did make sense to me.

I also know that there are things I can work on while I am in my job. For instance, I joined SCS – I am considering getting life coach certification. Would be super fun…and these are things I can do ‘in the meantime’ – so I am preparing myself for when I leave.

When I think about this and apply the model, it goes something like:
C = I stay in my job about 2.5 more years, in exchange for a payout.
T = If I do this I am selling out.
F = sad/guilty
A = Swirl! Not sure what to do. Second-guess myself.
R = Stay and feel like I sold out.

Here’s another model:
C = I stay in my job about 2.5 years.
T = I’m getting money to fund my dreams.
F = Peaceful
A = take the deal.
R = win/win.

And another:
C = don’t stay in the job, leave in April 2022.
T = I’m making a mistake to turn down a big payout.
F = scared
A = take less action because I didn’t take the payout
R = business could get off to a slower start.

Part of me says: You know that either way, this decision will be fine….and I suppose I also know that my dreams can come true if I do or do not stay in this job. Not sure why this feels like such a tough decision to make. Any insights/thoughts would be so helpful – thank you!