People-Pleasing, Self-Doubt and the Hidden Cost to Your Bookkeeping Practice

If you've spent any time around me, you've probably heard me talk about what I call the three dominoes of success:

Mindset. Productivity. Mechanics.

In that order.

Over the years, I've worked with thousands of bookkeepers from all over the world. Some are just starting out. Some are growing rapidly. Some are stuck in what I call the "booked but broken" stage, where the business looks successful from the outside but feels exhausting on the inside.

One thing has fascinated me for years.

I can give ten bookkeepers the exact same blueprint, the exact same systems, the exact same pricing strategy, the exact same marketing assets and the exact same coaching, yet the results can be dramatically different.

Some will build the bookkeeping practice and life they've always dreamed of.

Others will stay stuck.

For a long time, I found this frustrating because it didn't make sense. Surely if we gave everyone the same roadmap, they should achieve roughly the same outcome?

What I've come to realise is that success in a bookkeeping practice has very little to do with technical skill alone.

In fact, some of the most technically gifted bookkeepers I've ever met have struggled to build successful practices, while others with less experience have built thriving businesses with delighted clients, strong profit margins and genuine time freedom.

The difference is rarely intelligence.

It's rarely capability.

And it's almost never a lack of bookkeeping knowledge.

The difference is often mindset.

Most bookkeepers spend their time looking for better mechanics. They want to know how to find clients, how to price, how to build a team, how to become more profitable, how to use AI, how to productise their services or how to deliver better advisory.

Those things absolutely matter.

But they are not the first domino.

The first domino is mindset.

The second is productivity.

Only then do the mechanics really start to work.

I've seen this play out thousands of times. A bookkeeper will tell me they want more clients, but they're terrified of putting themselves out there. Another wants to raise their prices but feels physically uncomfortable at the thought of a client pushing back. Someone else knows they need to have a difficult conversation with a staff member but keeps putting it off.

Another has all the ingredients required to become an outstanding advisor but doesn't yet believe they have permission to step into that role.

None of those problems are mechanical.

They're mindset problems.

And here's the really important thing: that doesn't mean there is something wrong with you.

One of my favourite parts of my conversation with Simonne Liley was how much compassion she brings to this topic. Because often, when bookkeepers struggle with confidence, self-doubt or people-pleasing, they assume they are somehow broken.

They're not.

They're human.

Simonne knows this because she has lived it herself.

Today, Simonne is a highly respected leadership expert, speaker, coach and founder of Core Leadership Institute. She works with accountants, bookkeepers and leaders all over the world. Yet when she shared her story on the podcast, she spoke openly about being shy, nervous and deeply lacking confidence in her younger years.

If you met her today, you would never know it.

She's confident, articulate and incredibly insightful.

That's exactly why her message matters.

She's not teaching theory.

She's sharing what she's learned through lived experience.

One of the things she said that really landed with me was that there are always things happening outside our control and things happening inside our control. Most of us spend far too much time focusing on the external.

The economy. AI. Competition.

Clients. Accountants. Staff. Market conditions. Software changes.

Yet the biggest leverage point often sits much closer to home.

It's how we think.

How we respond.

How we lead ourselves.

I see this every day with bookkeepers.

A prospective client asks a question and one bookkeeper confidently explains the answer. Another bookkeeper knows the exact same answer but immediately starts second-guessing themselves.

An accountant queries a transaction and one bookkeeper sees it as a normal professional discussion. Another instantly assumes they've been found out and starts questioning their competence.

A business owner asks for a discount and one bookkeeper calmly explains their value. Another agrees despite knowing the work is worth more.

The mechanics are identical.

The knowledge is identical.

The outcome is completely different.

This is why I wanted to have this conversation with Simonne.

Because before we can build a thriving bookkeeping practice, before we can become the confident, capable professionals our clients need us to be, and before we can create the income, time, purpose and joy we are chasing, we need to understand what is happening beneath the surface.

And for many bookkeepers, one of the biggest things happening beneath the surface is something Simonne describes beautifully.

The people-pleasing pattern.

It's subtle.

It's common.

And it may be quietly holding your bookkeeping practice back far more than you realise.

---

The People-Pleasing Trap Quietly Holding Bookkeepers Back

When Simonne started talking about people-pleasing, I knew this part of the conversation was going to land with a lot of bookkeepers.

Not because bookkeepers are weak.

Not because they're incapable.

But because they are often some of the most caring, thoughtful and generous people you'll ever meet.

One of the things I love most about our profession is that bookkeepers genuinely want to help. They care about their clients. They care about doing a good job. They care about getting things right. They care about making a difference.

Unfortunately, those same qualities can sometimes become the very thing that holds them back.

Over the years, I've seen people-pleasing show up in countless ways inside bookkeeping practices. Sometimes it's obvious. Sometimes it's incredibly subtle.

It's the bookkeeper who keeps a difficult client long after they should have let them go.

It's the practice owner who agrees to "just one more thing" every month without charging for it.

It's the bookkeeper who delays increasing their fees because they're worried about what clients will think.

It's the person who knows they need to have a difficult conversation but keeps finding reasons to postpone it.

It's the bookkeeper who apologises before they speak.

The one who constantly seeks reassurance.

The one who quietly questions whether they're good enough despite years of experience and proven results.

On the surface, these situations all look different.

Underneath them often sits the same thing.

A desire to be liked.

A desire to belong.

A desire to avoid disappointing others.

One of the most interesting things Simonne shared was her explanation of where people-pleasing often begins. She talked about how many people learn early in life that being agreeable, helpful or accommodating creates connection. Being "good" earns approval. Being easy to manage earns praise.

Over time, those patterns become part of our operating system.

The challenge is that what may have helped us navigate childhood doesn't always serve us when we're running a bookkeeping business.

As business owners, we are required to make decisions that won't always make everyone happy. We need to charge appropriately. We need to hold boundaries. We need to manage scope creep. We need to address performance issues. We need to tell clients things they don't necessarily want to hear.

And if we haven't developed strong self-leadership, those moments can feel incredibly uncomfortable.

One of my favourite insights from Simonne was her distinction between the pleaser and the diplomat.

I think many bookkeepers worry that if they stop people-pleasing, they'll somehow become cold, difficult or selfish.

Nothing could be further from the truth.

The goal isn't to stop being kind.

The goal isn't to stop caring.

The goal isn't to stop helping people.

The goal is to become a diplomat.

A diplomat still cares deeply. A diplomat still wants the best for people. A diplomat is still compassionate, generous and thoughtful.

The difference is that a diplomat also tells the truth.

A diplomat can hold boundaries.

A diplomat can say no.

A diplomat understands that protecting their energy, time and wellbeing doesn't make them selfish. It makes them responsible.

This distinction is particularly important for bookkeepers because our profession is built on trust. Clients rely on us. They look to us for guidance. They want certainty and confidence.

Yet many bookkeepers are trying to lead others while struggling to lead themselves.

I often talk about what I call the "confident, capable professional." That's the version of ourselves our clients need to see. Not perfection. Not arrogance. Not bravado.

Confidence.

Competence.

Professionalism.

The challenge is that many bookkeepers don't feel like that person on the inside.

I remember being a startup myself. Every question felt like a test. Every challenge felt personal. If someone questioned something I'd done, I could easily interpret it as evidence that I wasn't good enough.

Over time, I realised something important.

The most successful bookkeepers aren't necessarily the smartest bookkeepers.

They're often the ones who have learned to back themselves.

They trust their training.

They trust their experience.

They trust their judgement.

And perhaps most importantly, they stop looking to everyone else for permission.

This is where people-pleasing becomes so costly.

Because every time we prioritise approval over honesty, every time we choose comfort over courage, every time we abandon our own needs to keep someone else happy, we reinforce a pattern that ultimately limits our growth.

Simonne described this beautifully when she talked about the relationship between belonging and self-abandonment.

That phrase stopped me in my tracks.

How many bookkeepers are abandoning themselves every day without even realising it?

How many are saying yes when they mean no?

How many are tolerating behaviour that shouldn't be tolerated?

How many are sacrificing their health, their relationships, their family time and their wellbeing in order to keep everyone else comfortable?

The irony is that most of them are doing it from a place of kindness.

But as Simonne reminded us, people-pleasing is not kindness.

True kindness includes yourself.

True kindness allows for honesty.

True kindness includes boundaries.

And true kindness recognises that looking after yourself is not selfish.

It's necessary.

Because when you continually abandon yourself, eventually something gives.

Your health.

Your confidence.

Your relationships.

Your energy.

Your business.

Something always pays the price.

That's why self-leadership matters so much. Not because it helps you become someone different, but because it helps you become more of who you really are.

A confident, capable professional who can care deeply about others without losing themselves in the process.

---

Everything You Want Is On The Other Side Of Putting Yourself First

One of the moments in the conversation that really landed for me was when Simonne said, “Everything you want is on the other side of putting yourself first.”

It is such a simple sentence, but for many bookkeepers, it will bring up a lot.

Particularly if you are a woman, a mum, or someone who has spent most of your life taking care of everyone else before yourself. For many of us, putting ourselves first has been conditioned as selfish. We have been praised for being accommodating, helpful, available and easy.

We have been rewarded for sacrificing our own needs and applauded for making sure everyone else is okay first.

But eventually, there is a cost.

I see it all the time inside the bookkeeping profession. A bookkeeper starts their practice because they want flexibility and freedom. They want to create a business that supports their family, gives them choice, and allows them to build a life on their terms.

That is the dream.

That is why so many bookkeepers step into practice in the first place.

But somewhere along the way, the practice starts running them instead of the other way around.

Clients dictate the schedule. Emails dictate the day.

Everyone else’s priorities become more important than their own.

Before they know it, they are working evenings, answering messages on weekends, skipping holidays, neglecting their health and wondering why the business they created for freedom feels anything but freeing.

This is why self-leadership matters so much. It is not just about business growth. It is not just about becoming a better leader, although of course it helps with that too. It is about creating a life that actually feels good to live, because there is no point building a successful bookkeeping practice if it costs you your health, your relationships or your joy along the way.

The goal is not simply to build a bigger business. The goal is to build a better life.

That is why I love helping bookkeepers create what I call a lifestyle practice. A practice that generates the income they want while still giving them the time, flexibility and freedom they originally set out to create.

But lifestyle practices do not happen by accident.

They require boundaries, courage, self-respect and, most importantly, self-leadership.

When Simonne spoke about putting yourself first, she was not talking about becoming self-centred. She was not talking about ignoring the needs of others or putting yourself above everyone else.

She was talking about recognising that you matter too.

Your health matters. Your goals matter. Your wellbeing matters. Your relationships matter. Your time matters. And if those things are constantly being sacrificed in the name of being “helpful”, something is out of alignment.

Because the reality is simple: you cannot pour from an empty cup. You cannot support your clients effectively if you are exhausted. You cannot lead a team effectively if you are burned out. And you cannot show up as the confident, capable professional your clients need if you are constantly running on fumes.

The bookkeepers who build thriving practices eventually learn this lesson.

They learn that boundaries are not barriers; they are protection.

They learn that saying no does not make them difficult, it makes them clear.

Charging appropriately does not make them greedy, it makes them sustainable.

Difficult conversations do not damage relationships nearly as often as avoiding them does. In fact, the conversations we avoid are often the ones that quietly drain the most energy from us.

One of the things I appreciated most about Simonne’s perspective was her focus on compassion. This is not about beating yourself up for getting it wrong. It is not about judging yourself for people-pleasing, lacking confidence or struggling with boundaries. It is about becoming aware of the patterns that are running beneath the surface so you can choose something different.

I often talk about what I call the Three A’s: Awareness, Acceptance and Action.

First, we become aware of what is happening. Then we accept it without judgement. Finally, we take action to create a different outcome.

That is what self-leadership looks like in real life.

It does not require perfection. It simply requires a willingness to notice what is happening and make a different choice.

That might mean making a different choice in a client conversation. It might mean making a different choice around pricing, boundaries, scope creep, team management or how you speak to yourself. It might mean noticing the moment you are about to say yes when you actually mean no, and instead pausing long enough to tell the truth.

That is where the change begins.

One of the other concepts Simonne touched on was the ripple effect of this work. When we change ourselves, we change the people around us. Our children are watching. Our teams are watching. Our clients are watching. Our communities are watching. The standards we set become the standards others learn from.

I have seen this happen countless times inside our community. A bookkeeper finally raises their prices after years of undercharging. Another lets go of a difficult client who has been draining their energy. Someone else starts protecting their calendar. Another finally hires support. A bookkeeper who has spent years doubting themselves decides to back themselves. And slowly, things begin to shift.

Their confidence grows. Their profitability improves. Their stress reduces. Their relationships strengthen. Their business becomes more enjoyable to run. Not because the mechanics suddenly changed, but because they changed.

That is the power of self-leadership. Perhaps that is the biggest takeaway from my conversation with Simonne.

Success is not just about knowing what to do.

Most bookkeepers already know far more than they think they do. The real challenge is having the courage to trust yourself enough to do it; to back yourself, hold boundaries, stop seeking permission, stop abandoning yourself in the pursuit of approval, and become the confident, capable professional you already have the potential to be.

At the end of the day, the bookkeeping practice of your dreams will not be built by technical skill alone.

It will be built by the person behind the practice.

And that person deserves your attention, your investment and your leadership.

If this conversation resonates with you, I encourage you to listen to the full podcast Episode 165 with Simonne Liley. Whether you are a startup bookkeeper, growing a bookkeeping business, or finding yourself booked but broken, the lessons in this conversation have the power to change the way you lead yourself, your practice and your life.

Because everything you want may very well be sitting on the other side of putting yourself first.