Do I have enough? As you approach making work optional, you begin to dwell on this question. Have I saved enough? Do I have enough? It’s certainly a subjective question because what’s enough for me may not be enough for you. It all depends on how much it costs to live the life you want to live and how you are going to live when work is optional for you.

But more than asking this question, I’d propose you ask yourself a second and third question:

  1. Do I have enough to do?
  2. Have I had enough?
  3. Do I have enough to do?

The second question “Have I had enough? really prepares you and your spouse to think about what you do for a living. Are you ready to leave your career? Have you had enough of the work you do, the clients you serve, and the people you work with? Are you truly ready to make work optional? (This may be easy for some of you to answer!)

But let’s say that you don’t have enough capital to make work optional, but you’ve had enough of your work? Now you are in a quandary and either make the decision to tough it out until becoming work-optional, or you consider a job change. Another option is to push out your work-optional date and find a job you will truly love. This may require you to work a bit longer than you anticipated. (Working in a job that you don’t like will wear you out and run you down. Life is too short to wallow in disappointment.)

The third question- “Do I have enough to do?”- gets you thinking about what you will do to occupy your mind and your spirit when work is optional. This is your bucket list for your mental well-being. You should complete your bucket list many years before you make work optional. This will help you focus on the freedom you’re running TOWARD and not just what you’re retiring FROM.

In my experience (and it may just be a generational thing), I find that men have a harder time transitioning from work to work-optional. Men want to work full-out until their last day and go from all work on a Friday to all play on a Monday. They tend to postpone thinking about what they will do when work is optional. I hear from time to time from men who say “When I retire I’ll figure it out.” And this couldn’t be further from the truth.

If you can’t find something you love away from work, then work is probably not optional for you yet. Maybe you won’t keep the same job you’ve had for 30 years, but some guys just love to work. Maybe you will need a part-time job or a less stressful full-time job to occupy your mind and your spirit. Maybe you can stay with the same company but in a part-time role. 

From my experience, those who wait until AFTER work is optional to figure out what they want to do spend many months pondering this idea and have a difficult time making a decision.

On the other hand, women seem to have an easier time transitioning from work to retirement. The women we work with seem to have a plan of things they want to tackle around the house or with family. They may start a new exercise program, take care of a loved one, watch the grandkids, finally sort through all the family pictures, declutter the house, or maybe get to work in the garden. 

So please, I implore you, think through the three questions above as you approach work being optional with your spouse and loved ones. Figure out the answers to these questions before you decide to turn in that pink slip and make it formal. You’ll be very happy you gave it some thought.