How do you know when it is time to retire?

General
1

Financially I believe I am there. We are 100% debt free including our home and have enough investments to yield a six figure income forever assuming a 4% withdrawal rate.

My business is debt free and as a result is extremely profitable with no payments. We are extremely busy right now and I would guess I can add 50k per month to my nest egg.

I am only 46 but am sick of working. 100% of it is traveling and it is hard on the family.

i feel like I would be an absolute moron giving up 50k/month income but when is it enough? I really am sick of my current situation but every month I work is $250/month additional in retirement funds. Basically every four months I work is $1,000 per month in retirement income for the rest of my life. Every additional year I work is $3,000 more per month in retirement.

It is pretty easy to say I will work three more years and have 9k more per month in retirement but how do you decide when to stop?

2

That’s a tough spot to be in. I had a smaller version of this dilemma a few years back—business was thriving, but I was completely burned out. I kept telling myself, “Just one more year,” but that turned into three. The money was great, but I was missing out on time with my family. Eventually, I realized no number was ever going to feel like “enough” unless I set a hard exit plan.

One thing that helped was outsourcing more, even bringing in a debt collection agency (Frontline Collections) to chase overdue invoices so I wasn’t dealing with that stress. If you’re miserable now, will extra cash really make up for lost time with family?