When Will Enough be Enough?

It’s never been a secret to me that I am a workaholic. I always approached it from my unique FI/RE perspective with this in the distance dream of never having to work again. As I have reached higher and higher income levels with more and more investments and companies I’ve worked on becoming successful I am once again faced with a question of “Is this enough?”

Since I was 20 years old working as a supervisor at UPS and doing a part-time job during the day I have always, and I mean always had at least 2 sources of income and one of them (except for a brief unemployment) has always been a full-time salary position. That 15 years of continuous income has led to a very comfortable life that has multiple sources of reliable income at any given time. This has allowed our family to have just me working and FIREMom can stay home full-time. 

Even going down to one income it is getting harder and harder to justify working the full-time job. This is despite the fact that I would rate this job a 9.5/10 in terms of how awesome a job can be. The pay is good, benefits are amazing, it has a pension, my coworkers are great, my direct reports do a reliable job, etc etc. Despite knowing that once May 2021 hits I will be vested in my pension and have it on my calendar as a sort of freedom date I am hesitant to even consider doing something else. 

Since in 5 months our family will be a version of LeanFire in May 2021 every day our family makes the decision for me to keep working is a conscientious decision to give up family moments in exchange for greater comfort, luxuries and experiences. 

With this post I am setting some goals that I can hold myself accountable to. I know myself well enough to think I’ll never reach a NW number that makes me feel 100% comfortable so instead I’ll set these goals to allow my future self the ability to leave full-time employment.

Goal  1  

Tax sheltered retirement > $500,000

Goal 2 

All business debt paid off

Goal 3

Paid off mortgage or after tax investments of equal amount

Goal 4

$250,000 in after tax investments

Goal 5

Reliable $50,000 in S-corp ownership income

Using current account values and savings rates I should hit these goals between 3 and 7 years from now depending on how the market does. That is still longer that I would like some days and honestly I know that even if I end up going 7 years that it is likely I’ll have moved the goal posts again. Although I hope to look back on this post and be reminded that this is enough money to lead a happy, safe and prosperous life. If this is more than enough to meet those needs then why keep going?