Why Enjoying Your Work Isn't Optional: A Strategic Approach to Building a Sustainable Business

My son said my vacation sounded like work.

I had just returned from a long weekend away with my husband, and when my son asked what I got up to, I enthusiastically described long beach walks, deep conversations, and working through my stockpile of self-development books.

His response? "That doesn't sound like a weekend off – that sounds like work."
My response? "It was pure pleasure."

If that word made you uncomfortable just now, that's exactly why I'm using it.

This conversation made me realise how many successful business owners have learned to keep work and pleasure in completely separate categories.

Why We're Uncomfortable Talking About Pleasure at Work

You equate pleasure with indulgence. And it's understandable, given how pleasure is typically marketed to us: Magnum ice cream, champagne brunches, spa weekends.

But indulgence is just one type of pleasure. And when that's the only version we see represented in media and advertising, we reject the whole concept as impractical for everyday work.

Here's what most high-achieving entrepreneurs miss: Pleasure can also simply mean getting genuine enjoyment from an experience.

I get enormous pleasure from my work:

• Watching clients grow their businesses with less struggle and more strategy
• The creative buzz of sitting down to write content that helps business owners
• Stepping away from my desk for a 10-minute break to cuddle our Golden Retriever, Suki (I have shared custody with my daughter – although she may dispute the "shared" part 😉)

But my relationship with work and pleasure wasn't always this integrated.

The Corporate Years: When Fun Was a Four-Letter Word

In my corporate career as a lawyer and executive, I had plenty of opportunities to enjoy my work more:

• The intellectual challenge of complex cases
• The satisfaction of solving difficult problems
• The camaraderie of working with a talented team

But I struggled to comprehend using "fun" and "work" in the same sentence – not if I wanted to achieve big goals. Not if I wanted to be taken seriously in serious environments.

Pleasure at work felt frivolous. Unprofessional. Like I wasn't serious enough about my career.

So I did what many of us do: I put my head down, worked hard, and told myself I'd enjoy life later. After the next promotion. After I proved myself. 

The problem? "Later" kept moving further and further away.

The Pattern That Follows You Into Entrepreneurship

When I started my coaching business, I carried that same mindset with me.

I told myself I didn't have time for pleasure. I had to do the hard work of building the business first. Fun could wait until I "made it."

Until I hit my first $100K year. Until I had a full client roster. Until I had systems in place. Until I could afford to relax.

Sound familiar?

Here's what I didn't realise: I was recreating the exact same pattern that had left me exhausted and unfulfilled in corporate.

I was building a business I would eventually resent – a business where success meant more work, more pressure, more hours, and somehow less enjoyment than I had as an employee.

The Pattern Most Female Entrepreneurs Fall Into

I see this pattern play out with clients who come to me for coaching.

They left their careers to have more freedom, more control, more flexibility. To build something they actually care about.

But somewhere along the way, they bought into the hustle culture story that building a successful business requires grinding, hustling, and sacrificing enjoyment now for some mythical future where they can finally relax and enjoy what they've built.

The Three Warning Signs You're Headed for Burnout

1. You're constantly thinking "I'll enjoy this when..." – When you hit a revenue milestone, when you have more clients, when you've "figured it out"
2. Sunday evenings fill you with dread – You're already dreading Monday morning and the work week ahead
3. You need elaborate motivation systems – Getting yourself to do the work requires willpower, rewards, or forcing yourself to focus

If any of these resonate, you're building a business on an unsustainable foundation.

The truth? I couldn't afford NOT to bring more pleasure into my work.

Not because I'm some enlightened person who always values joy over achievement (I'm not there - yet).
But because it works.

When I gave myself permission to enjoy my work, here's what shifted:

1. I Showed Up More Consistently (Without Needing Motivation)

I started looking forward to working every day because there was always something to enjoy, even on days when tech issues threatened to bury me in confusion. On those days, pleasure might be an extra cup of coffee or a bonus 10-minute sanity walk along the water.

The critical shift: I didn't have to drag myself to my desk anymore.
I didn't waste Sunday evenings dreading Monday mornings.
I didn't need elaborate reward systems or willpower to get myself to do the work.
The work itself became something I wanted to do.

2. I Had Dramatically More Capacity (Energy Management Over Time Management)

Think about how much mental energy you burn trying to motivate yourself to do work you don't enjoy:

• The internal negotiations
• The procrastination
• The guilt about procrastinating
• The forcing yourself to focus
• The resentment that builds throughout the day

When I actually enjoyed what I was doing, all that energy became available for the work itself.

I had dramatically more capacity for everything else – problem-solving, creative thinking, serving clients, building relationships.

This is what I mean when I tell clients that energy management is more important than time management. You can have all the time in the world, but if you're fighting yourself to use it, you'll accomplish far less than someone who genuinely enjoys their work.

3. I Got  Better Results (Enjoyment as Competitive Advantage)

This was the part that surprised (and delighted) me most.

My creativity improved. I started seeing solutions I'd been blind to before.
My problem-solving sharpened. I could think more clearly, more strategically.
My client work deepened.  I could be more present, more intuitive, more effective.

Turns out, enjoyment isn't the enemy of achievement – it's fuel for it.

The hustle culture lie is that you have to choose: either you're serious about success (and miserable), or you're having fun (and not really building anything substantial).

That's a false choice.

The Two Paths: What Actually Happens When You Grind Your Way to Success

I'm writing this because I know many entrepreneurs reading this are stuck where I used to be:

Believing that work has to feel like work if you want to achieve big goals.

That grinding and hustling your way through building your business now is the price you pay for the business you want in the future.

That's one formula for success.

But here's what I've seen happen to people who tried to grind their way there:

Outcome 1: They Burn Out Before They Get There

The most common outcome. They push hard for 2-3 years, hit a wall, and either:
• Shut down the business entirely
• Scale back so dramatically they're making less money than they would have in their former career – with none of the benefits

The business becomes unsustainable not because the model doesn't work, but because the founder can't sustain the level of effort required.

Outcome 2: They Build a Business They Resent

They hit their revenue goals. They have clients. They're "successful" by external measures.

But they've created a business that demands more from them than their corporate job ever did.

They're working more hours, with more stress, more responsibility, and somehow less satisfaction than when they had a boss and a steady paycheck.

The "freedom" they sought feels like a trap.

Outcome 3: They Hit Their Goal and Realise They Built the Wrong Thing

This is the quietest tragedy. They achieve what they set out to achieve – the revenue, the client roster, the "freedom."

And they realise they've created a job they hate. Just with more responsibility and no paid vacation.

Because they spent so long grinding toward a goal, they never stopped to ask: Am I building something I actually want to do every day?

The Alternative Path: Pleasure-Integrated Business Strategy

The hustle-and-grind approach says: Sacrifice enjoyment now. Push through. White-knuckle your way to your goals. Then you can relax and enjoy what you've built.

The pleasure-integrated approach says: Build a business you actually enjoy running now. Let enjoyment fuel your creativity and consistency. Create the future and the present you want.

One path gets you to burnout (or a business you resent).

The other gets you to sustainable success while actually enjoying the journey.

Why Pleasure Isn't Frivolous - It's Strategic Business Fuel.

Here's the thing most entrepreneurs miss: Pleasure isn't frivolous. It's fuel.

When you enjoy something, you're more likely to:

• Do it consistently (without needing motivation or willpower)
• Do it well (because you're engaged, not just going through the motions)
• Sustain it long-term (because you're not constantly fighting yourself)
• Innovate and improve (because you have mental space for creativity)

When you hate something, you're fighting an uphill battle every single day.

You might be able to force yourself to do it for a while through sheer determination. But eventually, something breaks – your health, your relationships, your business, or your spirit.

What Pleasure-Integrated Business Looks Like in Practice

I'm not talking about making your business "fun" in some superficial way.

I'm not suggesting you add ping pong tables to your home office or have mandatory fun on the agenda.

I'm talking about fundamentally redesigning how you work so that the actual experience of running your business is something you enjoy.

Real-World Examples

Restructuring your offers so you're doing more of what energises you and less of what drains you.

If VIP days drain your energy, consider restructuring your business around longer-term relationships. Make the same revenue with half the ENERGETIC cost. Enjoy your client work again.

Redesigning your schedule around your energy patterns instead of what you think a "professional" schedule should look like.

If you’re a morning person who does their best creative work between 6-10 am, schedule your client calls for the afternoons. Make your mornings a sacred time for the work you love most. Do your best work during your best hours and enjoy it.

Eliminating the tasks that make you miserable – even if you "should" be doing them or they seem essential.

If you hate social media. Hate creating content, hate engaging, stop. What if you tried building your business through referrals, strategic partnerships, and speaking instead?

Less reach. More revenue. Significantly more enjoyment.

Building in Pleasure Touchpoints Throughout Your Day

This is the smallest shift with the biggest impact.
For me, it's the 10-minute walk breaks. The good coffee. Writing newsletters and blog posts (which I genuinely enjoy). Coaching calls with clients.

These aren't rewards for getting through the hard stuff. They are the work. And they make everything else easier.

The Permission High-Achieving Women Need

Here's what I know about high-achieving female entrepreneurs (because I work with them every day):

You don't need convincing that pleasure would be nice.
You need permission to believe it's actually strategic.
You need evidence that enjoying your work won't make you soft, uncommitted, or less successful.
You need proof that you can build something substantial and enjoy the process of building it.

Why This Can Be Especially Important for Former Corporate Women

If you came from a corporate background—particularly as a woman in male-dominated fields—you may have learned early that showing too much enjoyment made you seem less serious, less professional, less committed.

You learned to separate "work you" from "real you."

You learned that achievement requires sacrifice, that success feels like struggle, that if you're enjoying yourself you're probably not working hard enough.

These beliefs don't serve you in entrepreneurship.

In fact, they actively sabotage your ability to build a sustainable business.

Because unlike corporate, where you could push through for the paycheck and benefits, in your own business there's no external structure holding you accountable.

If you hate what you're doing, you'll find ways to avoid doing it. Even if it's good for your business.

Your Permission Slip: Enjoying Your Work Is Fundamental, Not Frivolous

So here's your permission: Enjoying your work is not frivolous. It's fundamental.

Not because life is short and you should smell the roses (though that's true).

But because you literally cannot sustain a business long-term if you hate running it.

You can't out-discipline burnout. You can't out-hustle resentment. You can't willpower your way through a business model that makes you miserable.

At some point, something breaks.

The only question is: will you redesign your business before you hit that breaking point, or after?

The Bottom Line: Build a Business You Want to Run

You don't have to wait until you've "made it" to actually enjoy building your business.

In fact, if you wait, you probably won't make it. Or you'll make it and wish you hadn't.

The business you build through grinding becomes a grind to run.

The business you build with genuine enjoyment becomes something you want to sustain.
Your choice.