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  • San Chima

What regrets do entrepreneurs have?

Updated: Jul 1, 2023

Who wants to think about something as morbid as deathbed regrets? Well, there’s a good reason to think about them well ahead of time: you can prevent them. For entrepreneurs and business owners, many of whom will dedicate whole decades of their life to their work with little room for other things, the potential for regrets is perhaps higher.

So here I take a look at which regrets feature highly amongst entrepreneurs and business leaders, and how you can achieve your business goals without regrets.

The old cliché: I wish I hadn’t worked so hard

One nurse, Bronnie Ware, regaling her tales of the most common deathbed wishes, lends weight to the classic regret of working too hard by listing it as amongst her top 5 regrets of the dying. She wrote: "This came from every male patient that I nursed. They missed their children's youth and their partner's companionship. Women also spoke of this regret, but as most were from an older generation, many of the female patients had not been breadwinners. All of the men I nursed deeply regretted spending so much of their lives on the treadmill of a work existence."

Ah. So does this immediately pose a problem for entrepreneurs and those wanting success in business?

The answer is no, but with some caveats. If you want to succeed in business, and this isn’t just about regrets, you need to work smarter not harder. This is a huge underpinning principle of my coaching business.

Whilst hard graft is, in some ways and at some times, unavoidable, it shouldn’t be the norm, colouring every aspect of your life for years on end. Successful business founders and leaders are cleverer than that. It’s all about strategy and approach. Work-life balance is important, and even entrepreneurs need to give some thought to how their business goals can sit comfortably alongside family, relationships, health and wellbeing.

Being true to yourself

Success is a funny old beast. You may quantify it in financial terms, but the inner success you’ll feel at the end of the day will come from knowing you built your business on a foundation of your true values and principles. These differ from person to person. So knowing what yours are can be a stumbling block in itself.

Taking the time to establish your values and cement these into your actions will help you understand the right business direction to take, but also help you set and achieve the goals that matter to you and equal success on your terms. It’s a central part of my transformational business coaching approach.

One dying entrepreneur describes it as “I wish I had lived for myself.” They go on to explain: “Instead of reeling under the expectations of others, ask yourself what is it that you expect of your own self. What is it that you wish to achieve this year and how would success look like if you followed your heart and mind, if you listened to that inner voice.”

Indeed, it’s much easier to live a life which is true to yourself when you’re the boss, setting the direction and values of the business. What’s more, Bronnie Ware actually lists having the courage to live a life true to oneself as “the most common regret of all.”

So, simply by being an entrepreneur, you’re a step ahead of the rest. But take it the full way by uncovering your core values.

Risks, risks, risks

It would appear that the deathbed isn’t the place to be thankful for a life playing it safe. Not taking more risks is frequently listed as something to regret.

Those with entrepreneurial spirit are no stranger to risk taking. However, taking risks is, by nature, risky. The more successful you are, the more you stand to lose, and it becomes harder and harder to take the risks you need to take in order to grow, thrive and succeed.

The successful business is an agile business, and that involves taking risks. Lost opportunities have a nasty habit of becoming a sticking point in your mind for always, whereas risking and failing can always be a stepping stone to growth.

It’s relationships which matter

In one form or another, it’s relationships that people reflect on, and from which they get their sense of belonging and wellbeing. We are, after all, social beings.

First up are the personal relationships which are often taken for granted and fall by the wayside of an entrepreneur’s life. Passion for growing a business life can become all-consuming, and without the work smarter approach, can lead to there not being enough hours in the day to dedicate to loved ones. Relationships take time to nurture, and we all know the tales of the individuals who didn’t put in the time and discovered too late that the relationships with those they love have suffered.

When it comes to regrets, this isn’t just about familial and personal relationships. As Jayson DeMers, Founder and CEO of Email Analytics writes for Entrepreneur, when talking about the people you hire to help you along the way:

“Take it from me, an entrepreneur of multiple ventures: Who you put in those seats truly matters. A dedicated, hard-working, reliable, trustworthy worker is very different from one who’s there only to collect a paycheck. And beyond that, an amiable, fun, approachable worker is very different from one who’s antisocial or isolated. Take the time to find the right people for the job. It’s worth it.”

People matter. Given them time and care.

Listen to others

Similarly, entrepreneurs and the most successful business creators don’t operate in a vacuum; they listen to the advice of those with experience, and benefit from building a supportive network around them.

Delve into the background of any successful person and behind them you will learn about their mentors; the people who inspired them and encouraged them. Not building your own network, or not listening to others, can therefore end up being an enormous regret.

Surround yourself with your own squad. Sometimes that is easier said than done. One notable option is to get a business coach on board.

How business coaching prevents regrets

When we look at all the deathbed regrets of entrepreneurs there’s one way to make sure you avoid them, and that’s business coaching. An excellent business coach will help you uncover your authentic values, as well as help you work smart and invest in the relationships which matter. What’s more, the best business coaches tend to have been where you are; they have life experience as an entrepreneur and they fully understand the challenges you face.

Life is too short for regrets. And business life, as an entrepreneur, very much is part of your life. Book in for business coachingand discover how to be successful without harbouring regrets.

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