I’ve been retired for 3 years after building a successful startup – why is finding meaning in retirement still so hard?

A Reddit user built a successful startup, which gave him plenty of money to retire and set not just himself but also future generations up for financial success. Unfortunately, despite the fact he is in a great financial position, he said he is struggling to find meaning in retirement.

Here are some of the biggest challenges the Redditor says he is facing, along with some tips on how to make sure you’re prepared for these potential issues to arise if you retire early after achieving financial success. 

The challenges of early retirement — even when you’re rich

The OP outlined a few key challenges that he has faced since quitting work.

One of the biggest issues is that he’s spent his entire life chasing quantifiable and measurable goals, from getting good grades in school to building a successful company. Now that he is not doing that anymore, he’s having a difficult time finding meaningful things to do and goals to work towards that don’t have a set objective to achieve.  

He’s also found himself growing apart from colleagues, despite his best efforts, because he is no longer spending all day with them. While he values friendships from before he is rich, many of those old friends are still working and in a very different place from him financially. This makes it hard sometimes to spend time together or to do things like go on shared vacations due to the big money gap. 

He’s been able to find some new retired friends through hobbies he is pursuing, as well as through the FIRE Community online (a community of people who aim to achieve Financial Independence and Retire Early).  He’s also visited “rich people’ get-togethers but finds he often doesn’t have a lot in common with those individuals because many are trust fund kids and he wasn’t one.

Finally, he said he has struggled with potentially over-parenting his children since he quit his job in part to spend time with his young kids, and he’s now very cautious about pushing his kids too hard while at the same time making sure they understand their privilege and become productive citizens. 

How can you overcome these challenges and enjoy your early retirement?

Ultimately, the issues that the OP raises are all problems that anyone who retires early with a lot of money is going to encounter. And there are no easy fixes. 

One possibility is that the OP may decide he wants to continue doing work in some capacity, or even building another company if he thrives on doing so. There’s nothing that says he has to stay retired if it’s not working for him and if he misses having coworkers and clear company goals, he could find some type of part-time, consulting, or even full-time work he enjoys. 

He can also identify other specific concrete and measurable goals for himself, like traveling to a certain number of countries by a set date or achieving a specific fitness goal. Just because there aren’t pre-set goals determined by society or circumstance doesn’t mean he can’t create measurable objectives for himself. 

He should also make sure to focus on fostering the relationships that matter most to him, even if that means scaling down the vacations he takes so he can go with friends. And, as far as over-parenting his kids, if he is able to find other ways to fill his time, that issue should become less of a pressing one. 

The OP may also want to consider getting some professional help from a financial advisor who can help him organize his money life and prepare his kids for their wealth, and potentially from a therapist or life coach who can work with him to enjoy the early retirement he has worked so hard to achieve. 

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