Is there a Retire Early Retire Often Trap that one must be aware of? There sure is. First off if you are not familiar with this site and the Leisure Freak Retire Early and Often lifestyle then let me explain. You retire early and remain open to opportunities that interest you. Open to opportunities that lights your passions. The bonus is that you increase your wealth by being able to save and invest all of your earnings. Basically you get paid to do exactly what you want to do.

That said, before you retired the first time you were probably a go-getter in your previous career. The type of person who jumped in and got the job done. Even though you may not care much (I’m being nice) for the Corporate World and the way business is done, you build relationships. Relationships with the others on your team and extended team. Those team members aren’t the executives who come up with all the crappy policies. Making changes for change sake to shake up and anger the wage slaves.

I have been fortunate to accept a couple of opportunities that totally checked through “jobs I would like to do” items from my Bucket List. Now that I have done these things and have been at this last contract position for over 2 years, I am hearing that little voice in my ear. It’s telling me that it is time for retirement number two.

I have notified my contracting company manager of my plans. But haven’t had them tell the company I am at because of what I am calling the trap.

So what is the Retire Early Retire Often Trap?

There are a few issues that occupy my mind and has delayed my announcement for retirement #2.

Fellow Teammates:

Because this company I am at has had its share of churn. Either because they fire folks at the blink of an eye. Or people just can’t do it anymore and walk off the job. I know what will happen once I leave.

The leadership will wait until 2 days before I go. That’s when they will tag one or two folks to dump the work on. People who are already over-burdened with work.  Then have me transition everything I do to them.

I think the corporate leadership likes to wait to the last-minute so whomever gets dumped on doesn’t have time to find another position and quits. Quits and walks before the announced exiting employee leaves. This company I am at drags its feet for a couple of months before back-filling. That causes the existing teammates get mired in the increased work pile.

Having been on the receiving end of the dumping, I feel sorry for my teammates.  These people that I have built what I hope are personal relationships. I hope that we will someday again cross paths.

What I need to remember is that we are all replaceable in the tech business. This just comes with the territory. Sure people will feel the burden and adapt. Nothing is personal and if it goes how it has with me, any anger is directed toward the company for not getting off their ass and back filling the position.

Need vs. Greed:

This gig is very lucrative and I am funded until the end of the year. Leaving 6 months early of that end date is leaving a lot of money on the table that if I just stuck it out I could save and invest. This is what I think many will see as the biggest retire early and often trap to overcome. However, if staying in a position that no longer thrills me and lights my passions for the money, then I could have sleep-walked through several more years at my first career.

I don’t ever want to stay in a position to the point that I am no longer enjoying it or start to bitch about all the BS that keeps being shoveled on all the people who actually get crap done. My needs have been met in the time I have spent there and I don’t want to waste another precious minute of my life doing something just for money when it is no longer fulfilling and personally rewarding.

Fear of Never Making Another Dollar:

There are a couple of fellow consultants that work for my same company that know of my plans. The repeating caution I get is that I am at this time turning 56 very soon and no one will ever consider me for a position if I decide to pursue one. That by my taking this step there is no going back. Especially if I do as I am planning and taking a year off before contemplating another adventure.

Ok, I know there is age and long time-off work discrimination. But that’s the beauty of being a Leisure Freak who has his retirement funded and doesn’t HAVE TO find another job. If a company is that shortsighted then I wouldn’t want to be there either.

I know deep in my soul that if something else makes my Bucket List “jobs I would like to do”, that eventually I will be able to do it and if I don’t, I will be just fine. I treasure my freedom more than any job or position and won’t allow fear to dictate my retirement.

Is there a Retire Early Retire Often Trap? Yes, but it’s all in our head and we can overcome the trap by sticking to our plan. In my case, the plan where I live my life on my terms and enjoy the choices I have earned through FIRE. I will be letting the cat out of the bag next week.

Do you or have you experienced the above or any different thoughts that have delayed your announcing your retirement?