I had an award-winning company, 

88 staff across 5 countries

— but inside I was broken. 

The success wasn’t satisfying me.

It wasn’t until I fully understood what I wanted out of life that I realised my ideas of success were really dated.

In this post, I’ll share signs that your definition of success needs revisiting.

And how you can work out what your true ideas of success are to find more satisfaction in your business and life.

Why Update Your Ideas of Success?

Founders have stockpiles of ideas left unexplored and a long list of tasks that need to be done.

There’s a need to complete everything, and explore every possible idea “just in case”.

Sound familiar?

To make room for it all, you get locked into

  • Your own budget
  • Revenue targets with over-stretched goals
  • Short-term decisions that are not linked to long-term success

But are you chasing a clear vision?

Your Idea of Success

When Do People Typically Define Success?

Take yourself back to the moment you decided what success was.

…If you’re stuck with this — it’s okay. 

Few people can.

There are two common places where ideas of success are first established — in childhood, or from the internet.

As a kid, there would have been someone you thought was successful, a

  • Family member 
  • Teacher
  • Friend’s parent
  • Celebrities

In your formative years, it’s important to have someone to look up to so that you can start to discern concepts and ideas of how the world works. Success is a part of that — you start to have goals. 

But still holding what you deemed successful then… now — is out-of-date. 

You didn’t consciously choose it.

The other, more current success metric is the internet. You’re constantly looking others are achieving. In books, on social media, and through success stories. 

Whether you think it’s what you want or not. You start to compare what you have to what you perceive others to have.  

What do the two have in common?

Both of these ideas of success are external — and therefore, superficial.

They are defined by what you perceive someone else has. And don’t include the full picture — relationships, personal happiness and business. 

Questioning the Details of Success

When aim for this perception or subconscious idea of success, you chase what it “looks” like

 — a corner office, a 100-person team, a multi-million revenue number.

But when you get those things, it doesn’t feel right.


Quite simply — it’s not what you want. The reality is, success is much more nuanced. 

Before, you were looking at what success looks like from the outside. 

But success is a feeling

And to get it, you need to ask yourself what you want — in your personal life, and in your business. 

Ask yourself, what does success feel like to you? 

This question covers all aspects of your life — not just what your business can achieve. 

There are more details, it includes emotions that can’t be captured in an Instagram post or LinkedIn success story.

It feels much more personal. Like taking pride in your work, having quality time with family, and taking care of your personal well-being. 

Plan for Success

How Do You Work Out What Your Idea of Success Is?

When you look at success as a feeling — it’s often focused on some kind of satisfaction. But what creates that feeling? 

And how do you achieve that? Try this. 

Identify a Future Moment

Try to pin down one moment in the future that is your defining “success” moment. 

Perhaps, it’s a pipedream. Or it might be incredibly practical. 

What’s important is that this moment incorporates your business and personal goals. 

Creating separation between life and business is where dissatisfaction happens. You need both to go well to be truly happy.

Think about

  • Who are you with?
  • How does it feel?
  • What’s happening?

Picture it, identify each element, and get specific on the details. 

A good example of this is from a past client, his moment was sitting at a kitchen table in his house with his family, having just exited his business.

He was single and living alone in an apartment at the time.

Had he not looked at what success felt like, and been true to what that desire was, he wouldn’t have included the family element — only the exit cheque number.

Plan For It

When you know what you’re aiming for — both in business and in your personal life — you can be more focused on how to get there. 

Decisions are easier to make, because they are solely based on whether or not it edges you closer to those goals. 

But first, you need to plan for achieving those goals. 

When I work with clients I encourage a 5- to 10-year timeline, instead of the usual 3-year goals that founders find themselves in. It accounts for any big changes that might take longer to get to. 

With that 5-10-year goal, you can sequence backward. Take small steps that include taking care of yourself, your relationships, and your business. 

Because this is a long-term plan, it is less rigid in what you need to achieve and how you achieve it. 

And more focused on how you can have the energy to enjoy the journey of getting there. 

Be Future Fit

There is a logical fallacy that if you do more — you’ll be more successful. 

As founders, it’s a default setting to want to do more. If you don’t, you feel guilty about not prioritising the business. 

But when you do less and focus on high-priority tasks only — you can achieve so much more, and better serve your business as a result.

When you prioritise yourself and make sure you’re fit for the journey, you have more energy. 

This build-up of positive energy has a knock-on effect on your business, your relationships, and everyone around you. You can give more, it’s all very positive and it feels better. 


But how do you deal with the guilt of being a founder who’s prioritising themselves?

For me, there are two types of people that can act as accountability buddies in this transition into healthier ways of working

  • A coach
  • Peer groups of like-minded entrepreneurs

When you surround yourself with people on the same journey — it’s great motivation for you to keep going on your own.

Having someone like a coach to keep you accountable will help you to stay on track with your new goals and offer practical advice on how to sustain the momentum. 

Need Help Challenging Your Ideas of Success?

Taking the first step to get some perspective on what your ideas of success are is often the hardest. 

If you think you could benefit from having a coach to help you get there, and keep you accountable along the way — 1-on-1 coaching could be for you. Set up a discovery call today to see if we connect!