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10 Signs It's Time to Retire From Your Business - The Fortunate Investor


December 11, 2023 By The Saving Gal | This article may contain affiliate links. For more information visit our DisclosureIf you are a business owner, then your company is a little bit like your teenager; you love it, you have spent all of your time nurturing it, and now you cannot bear to see it leave you. So, it can be difficult to think about retiring, to say the least. The thing is, most of us do not want to work forever, and retiring can be really good for your health and wellbeing as you get older, so you really do need to plan to do so.
With all of that being the case, below we have put together a list of 10 signs that it could be time to retire from your business, so you know when it’s right to go.

Your Passion Has Left the Building

Remember when you used to wake up excited about your business? If these days you’re waking up feeling like you’ve been hit by a truck – a truck full of ennui and indifference – it might be a sign that you need to check out this Business Pricing Guide to Sell Your Business and think about moving on. Losing passion for your business is like realizing you’re more in love with pizza than your high school sweetheart. Sad, but inevitable.

You’re Using “Back in My Day” Way Too Often

If you find yourself starting every other sentence with “Back in my day,” it’s a hint. The business world evolves faster than a reality TV star’s career, and if you’re more comfortable reminiscing than innovating, it might be retirement o’clock.

The Tech Struggle is Real

Technology is to business what water is to a plant – essential. If the thought of using the latest software or social media platform makes you break out in hives, consider this your retirement flare gun. Unless, of course, you think fax machines are making a comeback.

Your Idea of Networking is a Family BBQ

Networking is key in business. If your idea of networking has slowly transitioned from industry events to chatting with your cousin about his new lawn mower at family BBQs, it might be time to consider retirement.

You Mistake Your Coffee for Your Smartphone

This one is self-explanatory. If you’re holding your coffee to your ear or trying to swipe on your mug, it’s either time for a vacation or time to retire. Or maybe just time to get some sleep.

Your Employees Look Like High Schoolers

When new hires start looking suspiciously like they should be in homeroom rather than the boardroom, it’s a sign. Sure, everyone looks young to someone, but if you’re constantly resisting the urge to ask, “So, what grade are you in?” then it might be time to step back.

You Think TikTok is a New Snack Brand

If you’re more out of touch with current trends than a 2000’s sitcom, then it might be time to consider retirement. It’s important to stay relevant, and if you’re still trying to figure out what a TikTok is, you might be a few trends behind.

Vacation Dreams are Now Retirement Dreams

Remember when you used to dream about short vacations to recharge? If those dreams have turned into fantasies of a permanent vacation in a sunny locale, complete with a beach and perhaps a margarita, retirement is calling your name.

Your Risk Tolerance is Now Risk Aversion

Business often requires a bit of risk-taking. If your attitude towards risk has gone from “Bring it on!” to “Oh no, not in my backyard,” it might be time to think about retiring. It’s okay – reruns of your favorite shows are a risk-free zone.

You’re Reading Blog Posts About Retirement

Let’s be honest, if you’re reading this, part of you is already contemplating retirement from your company, right? It’s like Googling symptoms – you’ve already diagnosed yourself; you’re just looking for confirmation that it is really the best thing for you to do, but really, the only person you need to consult is you.
As you can see, there are a lot of, actually pretty glaring, signs that it could be time for a person to retire from their business, no matter how much they love it. So if you spot any of these tell-tale signs in your working life, it could be a good idea to think about giving it all up and thinking about moving on to the next chapter in your life. Whatever you choose to do, we hope that it is the best thing for you!