How to Convince Yourself to Give Up Income and Retire

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I have a dilemma that may sound ridiculous but hear me out. I’m in my early 50s and want to retire for what feels like forever now but I can’t for the life of me calm my anxiety to leave so much money on the table by forgoing employment. I have $4 million dollars saved up and spend about $80,000 a year. I’m sure you know by the numbers already but every retirement calculator tells me that I have enough to quit for good, but I just can’t quite pull the trigger. Every time I am this close to finally telling my boss I’m done, my head wanders to the $200,000 I am giving up every year if I make the leap.

I grew up poor and I just can’t fandom giving up what could be $3 million or even $4 million by quitting now versus working until I’m 65. In the meantime, I’m burned out at work and I feel tired and exhausted all the time.

Am I insane? Because if I’m not quite there yet, I will be soon if I keep overthinking this. Help!

Take a deep breath! You’ve done very well for yourself, and you should take a step back and the finances you’ve built up for yourself. You didn’t say whether you were single or have a family, but the amount of money you’ve made is not only going to help you out, but it’ll help those around you as well. Congrats!

You should also know that your problem is actually more common than you think. I was just talking to my friend the other day and his numbers are even more extreme than yours. Like way more extreme. He’s worth $15 million dollars and he’s currently working at a job he dreads going for $50,000. Yet, he is hanging on and feeling miserable because he doesn’t want to give up that income.

Here is a list of things you and my friend need to do:

Convince yourself that there is no wrong decision to make here. There really isn’t! You are nervous that you’ll give up $4 million (gulp!) if you retire now, but what’s the point of having $4 million more if you won’t ever use the money? It’s one thing if you enjoy the work, but you feel miserable clocking in. You spend $80,000, so you had enough to retire roughly $2 million ago. You’ve already over saved for any reasonable future. What’s the point of accumulating more just for the sake of running up the score?

Try to spend a bit more money and see how your life and outlook changes. One thing I told my friend to do is to start spending more. He grew up poor as well, so he finds it difficult mentally to let loose even though he can clearly spend more. I told him to force himself to spend more. You should do the same. Maybe improving your lifestyle is just the ticket to brighten your mood so that you don’t mind the work anymore.

Consider a middle ground between having work and fully retiring. Talk to your boss about transitioning to part-time. Consider consulting in the same field and only taking on interesting projects. What about a complete career change? You can even start a business, but I caution you to only try this if there’s something specific you’ve always wanted to do and that it’s not going to cost a fortune to start up. After all, most businesses fail and someone late in their career who doesn’t need the money may not have the motivation to make it work.

Set a goal as the finish line, but only if you can set that in stone. You have $4 million now. What if your portfolio hits $4.5 million? $5 million? How about when you reach 55 and can start withdrawing from your 401k penalty-free if you wanted to? Use this time to find a target to retire when you hit it no matter what. Just make sure not to keep moving the goal post. If you wait until you are 55, then don’t keep dragging it out one more year. If you want to hit $5 million, then don’t turn $5 million into $5.5 million when you get there.

Find something to retire to. You didn’t mention whether you were single or have a family. This is easier if you have a spouse and kids of your own. But even if you are single, consider spending more time with your family and friends. Develop a hobby. Find something you love to do and add that into your routine. Once you find yourself with lots to do outside of work, you won’t have as much of an urge to clock in anymore.

Bottom Line

At my old job, there was a lady who worked hard and finally told the boss she was quitting work to travel after saving all her life. She made a few trips but she started getting sick 18 months into her retirement. She spent the next five years hopping from doctor to doctor trying to figure out what is going on, only to be diagnosed with Craniopharyngiomas, a rare form of brain tumor. She died one year later.

She was really healthy when I worked with her. Sometimes with health, it’s just the luck of the draw. You may live a long life, but you may not. What if you keep working and you find out a few years later that you only have a few years left to live?

Are you going to toil away at work earning money that means nothing to you, or are you going to finally spend your time enjoying what you’ve accumulated? Is it worth the stress and health to worry about the money you won’t need?

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  • BillyG says:

    This has got to be the top first world problem within the realm of first world problems. 🙂

    Good for her though!

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