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7 surprising things every business owner should do before they retire

Jeff Haden
Business Journalist

Jeff Haden is a bestselling ghostwriter, speaker, Inc. Magazine contributing editor, and LinkedIn Influencer

Jeff Haden
Business Journalist

Jeff Haden is a bestselling ghostwriter, speaker, Inc. Magazine contributing editor, and LinkedIn Influencer

Jeff Haden explores a few things you should tick off your business bucket list – from making a leap of faith to making a difference.

It is often quoted that "Twenty years from now, you will be more disappointed by the things you didn't do than by the ones you did do."

It’s very likely that one day all of us will look back and think, "What if I had done that? What if I had just said that? What if I had just tried that?”

So let’s avoid some of the potential, “What if?” questions you might find yourself asking when you’re living off your super.

To ensure your business life is exciting, challenging, inspiring – and hopefully more profitable – here are ideas to consider adding to your business bucket list:

A man walks towards the sun while an extended shadow is cast on the road

1. Enter a new market

Maybe that means opening a new storefront, selling certain products online, or converting a personal service into a set of web-based or app-based tools. While your new venture may be risky and may not be successful, you’ll learn a lot – and what you learn will definitely inform your next venture.

2. Decide to make a difference

You have enough on your plate just maintaining and growing your business, but someday you will look back and reflect on the difference you made, and not just on the lives of your employees. You’ll almost surely look back and wonder if you could have done more for your community.

And so will your employees.

It’s not hard. Offer testimonials to worthy causes. Offer to speak at an event, or donate goods or services to a fundraiser. If you aren’t sure how to help, call your favourite organisation and ask what you can do – they’ll have plenty of ideas.

Not only will you feel better about yourself, both now and “someday”, but your employees will feel more fulfilled and engaged by participating in efforts that have a larger purpose, too. 

3. Become more than one thing

We all possess a number of skills. Chances are you aren’t using most of those skills. You’ve chosen, rightly so, to specialise because that’s great for business, but it’s also bad for business – and bad for your sense of satisfaction. No matter how successful you may be in your specialty, there are surely other things you would enjoy doing and achieving. 

So go ahead. Decide what else you would like to do, and do it. Maybe you’d like to start a different business on the side or you’d like to teach or consult on the side. Or even just pursue a hobby that one day could turn into a profession, even if just a part-time profession.

When you look back you’re unlikely to regret the things you did; you’re most likely to regret the things you didn’t do. And that includes backing yourself and deciding that you are capable of being – even in a professional sense – more than one “thing”.

4. Be a mentor

Even though you gladly paid your dues, everybody wishes for a break – someone to recognise your effort, your potential and give you an opportunity to be taught and guided and mentored.

You can make it happen for someone else.

It’s easy. Pick a person working harder than the job requires. Pick a person always eager to grow and learn and develop. Pick a person who reminds you of a younger you.

And then take that person under your wing. I promise you’ll be glad, both now and years down the road, that you did.

5. Take a stand

Every business has one: a customer who constantly complains, who expects special treatment as a matter of course, who could be the poster child for “high maintenance”, and whose revenue is nice but whose margins are wafer-thin.

Bite the bullet. Explain you need to raise your prices. Explain that your level of service, while it will continue to be excellent, will not reach the heights your difficult customer expects. And if they walk, let them walk, and work hard to find customers that are not only more profitable but also result in better professional relationships.

Because after all: life’s just too short.

6. Tackle your fears

Whether it’s speaking publicly, taking advantage of media opportunities, taking on debt or a partner, or to sell off a portion of your business – everyone has fears. Whatever your fear, meet it head on.

Every person hoping to achieve great things gets scared. Successful people aren't braver than others; they just find the strength to keep moving forward. They realise fear is paralysing, while action creates confidence and self-assurance.

Pick something you'd love to do but are scared to do. Don't try to get over your fear. Accept that you will be afraid. And then go do it anyway. In the end you'll probably realise you were simply scared of the unknown – but you’ll never know if you don't try.

7. Take a holiday

Business success, no matter how grand, is not all that life is about. Fulfillment comes from more than just work: raising a family, or being part of a community, or genuinely connecting with the people you love….

So take a chance and take that trip. Your business will be there when you get back. And you’ll have created memories that will last forever.

And, ultimately, isn’t that what life is all about?


Work life balance is important for your personal success. Here are our top pieces of tech to get you home sooner.

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