Looking for some career advice.

I work in SaaS sales and now approaching 7 years with my current employer. The company overall is great, but recently I've felt burnt out and ultimately have been mulling over exploring opportunities externally.

While it hasn't been formally announced, the writing on the wall makes it fairly obvious that the company is looking to go public in the next year. I do have some equity in the company. Nothing crazy or life-changing but still something.

If I left the company today, they would still buy my shares back at the most recent price valuation. Would I be crazy to leave now and forfeit the opportunity to sell my shares at the IPO price?

What is the opportunity cost by staying?

Is it the start-up environment causing the burnout or is it a combination of daily life and work? If it is a combo, then your next job isn't going to satisfy the burnout.

If purely work... if you aren't leaving life changing equity behind then why wait? Can you find a new job that up-levels your career over night to make up for some of the difference?

I know quite a few people who instead of having 7 years at a pre ipo company, now have 10, 15, or 20. They keep waiting for their big payoff and it just doesn't ever come. To make matters worse, while the owners have promised them payouts (vague promises), they have nothing in writing... which means they have nothing.

I personally wouldn't use the possibility of a future payout in considerations a whole lot unless I had written guarantees.

Someone who has gone 0 for 3 on that fantasy of "going public and getting rich", I would move on with your life.

If you have a great relationship with a leader, I'd first talk to them about how you are feeling. I joined a startup in 2003 and it popped 10 years later, but I tried a couple more that I would have never purchased my options. Take a look at your option grant sheet to see what happens if you do decide to leave. Typically you have a window to purchase the vested shares within a certain amount of time or you lose them. Or maybe I'm confusing that with vested shares once the company goes public.

When you leave the shares you lose just go back into the company to do as they please.

If you don't have a ton of shares and are great at what you do (sounds like you are), you'll more than make up for walking away with a job you love and the commissions you'll earn.

Just my 2 cents. Once you leave just don't look back and think "what if". No difference between that and not buying a unicorn stock that ends up going big.