What Actually Makes Entrepreneurs Happy | 3 Keys To Happiness17 min read

The key to happiness as an entrepreneur is not more money, time, freedom, or clients. In fact, what actually makes entrepreneurs happy is very different from what you might believe. What actually makes entrepreneurs happy is thinking differently about the things that seem to make you unhappy on a day to day basis. In this article on the 3 keys to happiness for entrepreneurs, I share the the mindset shifts you need to make in order get out of the overwhelm, anxiety, and stress of entrepreneurship, and begin running your business with ease and enjoying the process along the way to success. If you’re an entrepreneur or ambitious human wondering what actually makes you happy and ready to find out how to feel happier as an entrepreneur (or as a human) on a day to day basis, this article is for you.

He towered over me at the refreshments table (the epitome of success with his fancy suit, fancy haircut, and shiny business cards). He flashed me a smile – not the kind that reaches your eyes, but the kind you give someone when attempting to make it through an evening of small talk without losing your mind. As our conversation deepened in a quieter corner of the room, he shared that his business was doubling in growth every year, but he wasn’t happy. He worked too many hours, he constantly felt overwhelmed or anxious, his relationships had been deprioritized for so long they were almost non-existent, and he hadn’t taken a real vacation in 10 years. “I was working so hard to create happiness, I didn’t recognize it as it walked right out my front door.”

I couldn’t help but wonder how many other successful entrepreneurs at this corporate event were unhappy on a day to day level…

After all, entrepreneurship allows for control over your time, no cap on your income potential, and the freedom to do work you truly love. Stuck in my 9 to 5 at the time, it was my ultimate dream. But did entrepreneurship always lead to burnout and daily dissatisfaction?

Fast forward a few years, babies, and certifications later, and now I jump out of bed in the mornings to work with entrepreneurs who want to achieve more happiness, fulfillment, AND success in life and business. Through powerful one on one coaching conversations I help them get clear on what they really want (not what they’ve been told they should want), uncover their limiting beliefs and start thinking differently so they can stop sabotaging their own success, and hold them accountable to doing the stretchy, uncomfortable things that they need to do to achieve their goals in life and business.

What I’ve learned over years of coaching powerful entrepreneurs is that most are, at a high level, generally satisfied to some extent with the way their lives have turned out. But on a day to day level,  they are overwhelmed, anxious, and exhausted.

If you’re wondering “are entrepreneurs happier than employees?”, “what actually makes you happy as an entrepreneur?”, and “what are the keys to happiness?”, you’re in the right place.

This article will outline the biggest misconceptions about happiness, what actually drives happiness and fulfillment for entrepreneurs, and the mindset shifts that are critical to loving the life and business you’ve built.

Related post: The 4 Biggest Things Holding You Back In Life

Why are entrepreneurs unhappy?

If you’re running your own business but you don’t feel happy or fulfilled, there’s probably one of three things going on.

A vision out of alignment with your values

Maybe you’re running a business that doesn’t light you up. Maybe you’re working toward a future that you don’t actually want (but perhaps you feel you should want it, or you should be grateful you have it). Essentially, you’re living someone else’s life. 

I’ve seen this with clients that worked so hard to build passive income businesses, only to realize they actually really like “active” income and want to work.

I’ve seen this with entrepreneurs that have spent 10 years in an industry because it matched the degree they decided to get at 17, but had no passion for it. 

I’ve seen this with entrepreneurs that felt obliged to step into family businesses, but had very little genuine interest in doing so.

If your business is out of alignment with your values, or the life you truly want for yourself, you will encounter resistance every step of the way, and happiness will be so much more difficult and limited.

Working toward someone else’s dream is not only exhausting, but counterproductive (don’t build a business, career, and life that feels wrong to show up for!)

The stories your brain tells you to keep you safe & stuck

The reason so many entrepreneurs experience excessive anxiety, overwhelm, and exhaustion is because of the stories they tell themselves. 

The brain’s job is to maintain the status quo to keep you safe. In order to do that, it filters the information coming at it and assigns meaning to it based on the beliefs you’ve adopted over the course of your life experiences. Your brain’s interpretation is subjective, and often misrepresents reality. But you believe it nonetheless, and it creates a negative experience in the day to day running of your business.

You see this in entrepreneurs whose businesses are successful and increasing in revenue year after year, but who worry excessively about everything falling apart. Their brain is feeding them the story that their success is too good to be true, that they won’t be able to handle success at the next level, that it was all just a fluke and won’t happen again next year.

What actually makes entrepreneurs happy and what are the keys to happiness for entrepreneurs as explained by best life and business coach Ana McRae

You see this in entrepreneurs who work excessive hours to hit their business goals and fail to prioritize their relationships, their health, or their hobbies. Their brain is feeding them the story that success requires hard work and sacrifice, that they don’t have time to play, that their worth depends on the amount of things they accomplish in a day.

When you are not aware of the automatic thought patterns sparked by your limiting beliefs, they subtly affect your daily decisions and actions and the way you experience running your business includes stress, anxiety, and exhaustion.

A strategy out of alignment with you or the goal

If your vision, values, and business are aligned, and you’re proactively managing your mindset, then you’re probably ‘fine.’ But if you’re wondering whether there’s more to life than this, or you’re not feeling fulfilled, then it’s quite likely that your strategy is out of alignment with your goal. Perhaps your goal is not big enough and it isn’t challenging you to stretch to the edge of your comfort zone. Or perhaps the strategy itself isn’t right for you.

You see this in entrepreneurs using social media for marketing when they hate spending time on screens.

Or in CEOs who fail to leverage their teams, and spend the bulk of their time operating outside of their unique zone of genius (for example, spending 30 hours a week delivering services, when what they’re most excited about is having business development conversations).

Related post: How To Shake Up A Monotonous Life

If your strategy is out of alignment with you or the goal, your business can still “work” and “grow”, but the running of it is less than exhilarating.

These are just a few of the things that make entrepreneurs unhappy on a daily basis. But what do we believe makes entrepreneurs happy?

Misconceptions about what actually makes entrepreneurs happy

Studies have shown that entrepreneurs are generally happier than employees. 11,000 graduates surveyed about their happiness levels in a research study by Wharton showed that the biggest predictor of happiness was entrepreneurship. People running their own businesses were happiest, regardless of how much money they made.

But once you launch your own business, the things that you expect to actually make you happy as an entrepreneur, are not the things that actually do.

When entrepreneurs come to me for our first coaching call, they usually want either more revenue, more clients, or more freedom. They’ve spent weeks, months, and years working toward the next level in these areas, while happiness took a backseat. 

Entrepreneurs think more money will make them happy

The multi-billionaires who’ve achieved mind blowing amounts of financial success keep saying this isn’t true, but most people don’t seem to believe it until they reach that same level (usually many decades and disappointments later).

“Too many people measure how successful they are by how much money they make or the people that they associate with. In my opinion, true success should be measured by how happy you are.”

Richard Branson

More money isn’t what makes entrepreneurs happy… what makes entrepreneurs happy is actually a sense of financial security. Safety and security is a core human need, but the amount of money you earn doesn’t directly contribute to your sense of security. 

What actually makes entrepreneurs happy and what are the keys to happiness for entrepreneurs as explained by best life and business coach Ana McRae

I’ve worked with entrepreneurs that have sold multi-million dollar businesses and could afford not to work for the rest of their lives, but still felt the pressure to apply for a job. The deeply ingrained beliefs that “your worth is determined by how much money you make” or “you need to make more money, period” will prevent you from feeling secure financially, despite the reality of your situation.

Other entrepreneurs left their full time jobs when their businesses were making less than $500/month because they felt financially secure in their future.

As you can see, it’s all in your head.

The biggest factor determining your happiness isn’t your situation, but your mindset about it


The amount of money in your bank account isn’t what makes you happy as an entrepreneur.

Your mindset about your financial situation is what makes you feel secure, and thereby happy.

Related post: How to achieve success as an entrepreneur

Entrepreneurs think that clients falling from the sky will make them happy

So many entrepreneurs come to me wishing I could make their problems go away with a magic wand, but fail to realize that that would eliminate the sense of satisfaction they get from solving their problems in their own way.

Yes, more clients that you didn’t have to work for would be great. But if that’s all your business consisted of, you’d get bored very quickly.

What actually makes entrepreneurs happy is the sense of accomplishment after overcoming challenges that stretch you to the edge of your comfort zone.

Working through your own problems (not the lack of problems) is what actually makes entrepreneurs happy.

You likely became an entrepreneur because your job was boring, you wanted something more mentally stimulating and personally fulfilling.

You came for the challenge. Don’t forget to remember that you love challenges.

What actually makes entrepreneurs happy and what are the keys to happiness for entrepreneurs as explained by best life and business coach Ana McRae

What actually makes entrepreneurs happy is not easy success, but stretchy accomplishments.

This is another mindset shift.

Catch yourself wishing business was easier or you didn’t have X problem, and remind yourself that your fulfillment comes from solving the problem.

If the problem didn’t exist in the first place, you’d be bored out of your mind.

You are wired to solve problems.

Entrepreneurs think more freedom will make them happy

A lot of business owners wish they could spend less time in their business, and more time gallivanting across the globe. They idolize passive income businesses that allow them to travel full time while someone else deals with the pains of managing a company.

I’ve had clients who spent ages planning to launch passive income businesses, only to realize they want an active income business.

But the social narrative around making a ton of money without doing a ton of work keeps people from pursuing careers they love that are more involved.

What actually makes entrepreneurs happy isn’t a wide open calendar with nothing to do, but the freedom to do things you find purposeful and valuable.

YOU get to decide what brings you purpose and joy. And if it ties you to one location, that’s okay too. If it requires hard work, that’s okay too. There is no one definition of success.

Related post: How To Achieve Success As An Entrepreneur

Entrepreneurs think finishing the next project will make them happy.

Entrepreneurs are some of the most driven and ambitious people I’ve met, with endless creative ideas that they are working on bringing to life. 

This only becomes a problem when you expect the completion of a project to make you happy (falling prey to the “arrival fallacy”), rather than focusing on experiencing happiness along the journey.

women smiling and displaying a happiness mindset

What actually makes entrepreneurs happy is balancing life alongside business: authentic relationships, belly-laughs, purposeless play, and all the other things that help you manage your energy. When you focus on having fun, you feel happier on a day to day basis.

The level of happiness you feel on a daily basis directly affects the results you’re able to create in your life.

Related post: Finding Balance In Life: Achievement vs Enjoyment

“Most people would assume my business success, and the wealth that comes with it, have brought me happiness. But I know I am successful, wealthy and connected because I am happy. I wholeheartedly believe that happiness should be everyone’s goal.”

Richard Branson

This is why my clients can reduce 50 hour work weeks to 15 hour work weeks and still run thriving businesses while feeling more fulfilled on the daily. Because your business doesn’t depend on hard work and sacrifice. On the contrary, it takes off when you’re having a whole lot of fun. 

Related post: The ONE Thing That Will Grow Your Business 30X

The mindset shifts that actually make entrepreneurs happy

There are many mindset shifts that need to happen for you to run a thriving business while living a fulfilling life. Many of us have been told a lot of things about entrepreneurship that aren’t necessarily true, and keep us from fully experiencing happiness daily.

If you want to actually love your life and business, you need to reframe your thinking.

“I need to make more money to be happy” becomes “I’m financially secure already. I need to focus on being happy in order to continue building wealth.”

“I wish this wasn’t so difficult” becomes “I am 100% capable of solving any challenge I come across, and love the process of doing so.”

“I wish I had more time” becomes “I am so grateful that I get to spend my time doing work that fulfills me.”

“When I achieve/complete X, I’ll be so happy” becomes “I get to feel happy right now, even though my to-do list will never end.”

How to change the way you think & improve your mindset

The bottom line is, the amount of happiness you’ll experience in your entrepreneurship journey depends entirely on your mindset.

If your thoughts are preventing you from feeling happy on a day to day basis, no amount of money or success is going to magically change that. 

Mindset work is the key to not only creating mind blowing success, but experiencing happiness and fulfillment in the journey.

Related post: Daily Mindset Practice for Business Success | How To Create a Mindset Routine

In this article I wrote about the science behind mindset work (how your thoughts actually influence your results in life, backed by neuroscience) I explain the 3 simple steps to stop self sabotage and start rising to your full potential.

First, identify subjective beliefs you’ve assumed to be facts from your past experiences. For instance, you might believe you’re not good at public speaking because of a past failure.

Second, question these thoughts. Ask yourself if they serve your goals. Can you view your public speaking skills differently? Maybe you’ve improved over time.

Lastly, practice new thinking daily. Choose empowering beliefs. If you catch yourself thinking you’ll always be a bad public speaker, consciously shift to ‘I’m getting better.’ Your brain can adapt with time – it’s like training a muscle.

Related post: How To Practice Mindfulness

How coaching actually makes entrepreneurs happy

As Marcia Reynolds so eloquently explains in her book Coach The Person, Not The Problem (aff link) the goal of coaching is to stop and question the thoughts and behaviors that limit your perspective, so that you can see a new way forward to achieve your goals. Instead of thinking about the problem, you examine the thinking that made the issue a problem in the first place. Instead of quickly jumping to solutions, you reflect on the beliefs and perceptions that can change your view on what actions to take moving forward. Coaching is the process of partnering in a thought provoking conversation that inspires you to maximize your personal and professional potential.

The most intelligent people need the most help thinking about their thoughts, because they are masters of rationalization.

Business growth is never about the money. Business growth is about creating something that aligns with your deeper purpose, stepping into your full potential as a leader, and having fun running your business while living a life that you love. From there, money is a natural side effect. 

As a business coach, I help entrepreneurs operate at peak performance so they can achieve unprecedented levels of success and fulfillment. If you’re a small business owner ready to reclaim your time and energy and grow a thriving business while balancing a fulfilling life, let’s have a conversation about how coaching can help you get there faster. Learn more about my 1:1 business coaching program, or book a free connection call with me below.

Drop a comment below, what was the biggest reason you decided to become an entrepreneur?

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