After Decades in Executive Roles, Can I Transition to a 9-5 Job and Keep My Benefits?

One of the best aspects of participating in the FIRE (financial independence, retire early) movement is that once you hit your target number, you can either retire or step into a lower-stress role. In many ways, sticking with lower-stress roles while easing into retirement will let you enjoy more time in your day while still allowing income. 

This is exactly the situation with one Redditor who posted in r/Fire, asking if it’s possible to easily transition from a high-level executive position to more of a 9-5 role. The hope is that they can discover whether others have done something similar and how successful this transition really was. 

It goes without saying that most people in high-stress roles would love an opportunity to move on to something that doesn’t make them hate going to work the next day. In this regard, we empathize with this Redditor in a big way. 

The Big Question 

As it stands today, our Redditor is a high-level executive in a financial role looking to potentially shift from his stressful, demanding career to more of a 9-5. They are very much looking to learn and understand what options are available if they walk away from the intensity of the corporate world. In its place, they want to move into a role that still offers benefits like employer-sponsored healthcare and stick with it until they reach the Medicare age of 65. 

Ultimately, healthcare is the biggest driver here, as they don’t want to be in a position where they need to utilize ACA plans. The original poster feels this will cost more in the long run, especially if you have multiple family members on a plan. 

This Redditor hopes to learn how others have handled similar transitions and to what degree of success they were able to walk away from the money into lower-stress opportunities. They are considering roles like a finance director position at a private school, a small restaurant chain, or a small office. There is also an option of getting out of finance altogether and becoming a librarian, so options are plentiful. 

Reddit Responds

While there is an onslaught of comments in this thread about looking at volunteer roles at non-profits, etc., the original poster pushes back pretty fast. They are concerned that non-profit opportunities would likely not come with the necessary health benefits they want to maintain. 

They also indicate that transferring internally at their own company isn’t an option. They don’t believe that someone could successfully transition from a high-level to a clerical role internally in the current company. 

When the subject of potentially moving into freelance or consulting comes up, the Redditor doesn’t shut it down completely, but says they aren’t interested in chasing future clients on the regular. They might consider going to work at Costco, as one Redditor suggested as this is more enticing to them than freelance. 

The original poster does enjoy hearing about how one Redditor in the comments went from a VP at a digital advertising firm to selling paint at a local Sherwin-Williams. This commenter indicated their stress level dropped by 80%, which certainly caught the original posters attention. 

In the end, there are more than a dozen comments in this post from people who have done something similar, and all of them recommend the transition. While they say it won’t be easy, especially if they are working for people less qualified than them, once they get over the initial hurdles, the change is 100% worth the move. 

The Bottom Line

If the biggest question is whether this Redditor can find a role with benefits, the answer is unequivocally yes. Any full-time retail position or in-office role at a small company would likely offer the healthcare benefits the Redditor doesn’t want to lose. While costs will vary based on the business and benefit level, there is little question they will be better and less expensive than ACA plans. 

The hope is that this individual will find their way, whether it’s working at a non-profit, Costco, or potentially even as a local bank teller. Their finance background would almost certainly get them to the top of a resume pile, at least that is the hope. 

The post After Decades in Executive Roles, Can I Transition to a 9-5 Job and Keep My Benefits? appeared first on 24/7 Wall St..