The Three Questions Every Successful Professional Over 50 Should Ask Before Trying To Become Healthier

This article explores why successful professionals, business owners, and leaders over the age of 50 need a different approach to improving their health, fitness, and wellbeing. Using the powerful framework of "Ready, Willing & Able," health coach Chris Deavin explains how readiness, willingness to change, and the ability to overcome obstacles determine long-term success more than motivation alone. Learn how busy professionals over 50 can build sustainable habits, improve resilience, maintain strength and energy, and create lasting health change while managing demanding careers, family responsibilities, and the realities of ageing.

One of the things I’ve observed after more than 25 years of coaching is that successful people rarely lack intelligence, discipline, ambition, or the ability to solve complex problems.

They build businesses from the ground up. They lead teams through uncertainty. They manage pressure, navigate setbacks, and deliver results consistently over decades. They understand that meaningful success requires commitment, structure, and resilience.

Yet despite being highly effective in almost every other area of their lives, many professionals, business owners, and leaders over the age of 50 find themselves feeling frustrated when it comes to their health.

They know they want more energy. They want to lose weight. They want to improve their fitness, build strength, reduce stress, and stay healthy enough to enjoy the next phase of their lives. But despite their best intentions, they often find themselves trapped in a cycle of starting, stopping, and starting again.

What I’ve learned is that this rarely happens because people lack capability.

More often, it’s because they haven’t stopped to assess whether they’re truly ready, willing, and able to make the changes they want.

In business, when we’re faced with a major challenge or opportunity, we don’t simply jump into action and hope for the best. We assess the situation. We consider our resources. We identify barriers and risks. We decide what we’re prepared to commit to and what success will require.

I believe we should approach our health in exactly the same way.

That’s why one of the first exercises I encourage clients to complete has nothing to do with calories, exercise programmes, supplements, or health trackers. Instead, I ask them three deceptively simple questions:

• How ready am I to change?

• How willing am I to do things differently?

• How able am I to handle the obstacles that will inevitably appear?

The answers don’t have to be perfect. They simply provide an honest assessment of your starting point. And in my experience, lasting change always begins with honesty.

Are You Ready?

Readiness is often misunderstood.

Many people assume that because they want to improve their health, they must be ready to do so. But wanting something and being prepared to act on it are not always the same thing.

I’ve worked with countless business leaders who desperately wanted to improve their health but were simultaneously navigating major work projects, caring for ageing parents, managing family commitments, or dealing with significant life stress.

In these situations, the issue isn’t motivation. The issue is capacity.

You may know that your health needs attention. You may be worried about your weight, your blood pressure, your energy levels, or your physical fitness. You may feel frustrated that you’ve allowed your own wellbeing to slip down your list of priorities.

But if you’re honest with yourself, are you truly ready to allocate the time, energy, and attention required to begin making changes?

Acknowledging that you may not be fully ready right now isn’t an excuse. It’s self-awareness.

In fact, recognising what is preventing you from being ready is often the first step towards becoming ready.

The question isn’t simply whether you want to change. The question is whether you’re prepared to make your health important enough to change.

Are You Willing?

This is perhaps the most uncomfortable question of all.

Because willingness requires us to confront reality rather than preference.

Many professionals tell me they want better health, more energy, and improved fitness. But when we explore what achieving those outcomes actually requires, they often discover a gap between what they want and what they’re willing to do.

Are you willing to leave work on time so you can exercise, to prioritise sleep over another hour spent answering emails, to spend time preparing meals rather than relying on convenience, to train for 30 minutes when you can’t find time for an hour, and to feel uncomfortable, tired, or inconvenienced in the short term in order to achieve something meaningful in the long term?

The truth is that many successful people have become exceptionally good at prioritising everyone and everything else before themselves.

Their clients come first.

Their teams come first.

Their businesses come first.

Their families come first.

And somewhere along the way, their own health becomes something they’ll address “when things calm down.”

Unfortunately, for most successful people, things rarely calm down. At some point, improving your health requires making the decision that your wellbeing deserves the same level of commitment and attention that you’ve already given to building your career.

Are You Able?

Most people assume ability means physical capability. In reality, ability is far broader than that.

Do you have the time, energy, support, knowledge, resources, environment, and accountability necessary to follow through consistently?

One of the greatest differences between professional success and health success is that work naturally provides structure.

You have meetings, deadlines, calendars, accountability, systems, and consequences.

Your health, on the other hand, often has none of these things. It is left to spare time, spare energy, and good intentions.

This is one of the reasons why so many highly capable people struggle to maintain healthy habits. Not because they lack discipline, but because they lack the structure that supports discipline.

The solution isn’t necessarily to become more motivated. It’s to become better supported.

When clients begin creating systems, routines, accountability, and environments that make success easier, consistency becomes far more achievable.

Understanding Your Resistance

Over the years, both through coaching and through my own experiences training for endurance events and ultra-marathons, I’ve learned something important:

Resistance is normal.

Almost everyone experiences thoughts such as:

• “I’ve tried this before.”

• “I don’t have enough time.”

• “I’m too busy at work.”

• “I’ll start after this project finishes.”

• “I’ll probably fall off track again.”

• “What’s the point if I can’t do it properly?”

Many people believe these thoughts are evidence that they lack discipline or commitment.

They’re not. They’re simply evidence that change is difficult.

The goal isn’t to eliminate these thoughts. The goal is to become aware of them.

To notice them. To name them. To understand where they come from.

Because once you understand your resistance, it begins to lose some of its influence over your decisions.

You stop seeing resistance as proof that you can’t succeed and start seeing it as information that helps you prepare more effectively.

Building Resilience Instead of Chasing Perfection

The professionals, business owners, and leaders who create lasting change aren’t necessarily the smartest, the strongest, or the most disciplined.

They’re the ones who become more aware and more adaptable.

They’re the ones who expect setbacks and learn how to recover from them quickly, and understand that consistency isn’t about perfection.

It’s about resilience.

It’s about developing the ability to continue moving forward despite pressure, setbacks, stress, travel, family commitments, busy periods at work, and the countless other challenges that life inevitably presents.

They don’t aim to avoid failure. They aim to become better at restarting.

So before asking yourself what diet to follow, what exercise programme to start, or what health goal to pursue next, perhaps ask yourself three more important questions:

How ready am I?

How willing am I?

And how able am I to handle what comes next?

Because lasting health change doesn’t begin with the perfect strategy. It begins with an honest assessment of where you are today and a willingness to build the resilience required to move forward.

Ready To Build Your Executive Health Plan?

If you’re a business owner, senior leader, or high-performing professional over 50, your health should support your career, not compete with it.

The challenge isn’t knowing what to do. It’s creating a realistic plan that fits around your workload, responsibilities, travel, family commitments, and professional goals.

That’s exactly what we discuss during a complimentary Discovery Call.

Together, we’ll look at:

• Your current health, fitness and lifestyle

• The biggest obstacles preventing consistency

• Your professional and personal goals

• How your health can better support your performance

• The habits, systems and accountability you need to succeed

• A realistic strategy that works within your schedule

By the end of the call, you’ll have greater clarity on what needs to change, where to focus your efforts, and what a personalised health plan could look like for you.

Because the goal isn’t simply to get healthier.

The goal is to build the energy, resilience, strength and physical capability needed to perform at your best in business and life for years to come.

Book your complimentary Discovery Call today and let’s create a health strategy that works alongside your career, not against it.

“You already have a strategy for your business. Isn’t it time you had one for your health?”