The Prosperous Entrepreneur

You can make millions and still be miserable

Published 26 days ago • 2 min read

Michelle Nicole Martin

Leadership & Performance Coach for Small Business Owners

Hey Reader, I'm sure you have had this thought before:

"Once I reach XX in revenue, I'm never doing [these tedious tasks] again! I’ll be doing [these awesome things] instead!"

My list of awesome things includes Pilates, which is strange. I have never been to Pilates, but heck! It's in the dream!

Whatever your dream is, much like my Pilates, it's probably a symbol of relaxation and having time to think your own thoughts in peace. And whatever it is, it doesn't include things like invoices, networking events, or high-maintenance customers!

Would it surprise you to know that every one of my clients, regardless of their financial success, keeps waiting for their dream day to come true?

I recently had an eye-opening conversation with a client whose company has reached an impressive milestone of $5 million.

When we talked about his ideal day, he laughed it off, minimized it, and called it selfish.

This is confusing to me. Why? Because this particular client hired me to specifically help him reach this goal!

Intrigued, I asked, "What's so selfish about it?" This question revealed a deeper issue—he felt guilt and shame about living out his dream day.

This got me thinking: why do we, as entrepreneurs, work so hard to build a business that supports the life we want, only to hesitate when we actually have the opportunity to take it?

The truth is, it's not just about having the time and money. We need to understand and overcome the internal barriers that hold us back from enjoying what we’ve accomplished.

Here are five reasons you might never have your ideal day:

1. Identity and Self-Worth Tied to Work

Your sense of self-worth is often closely linked to your work and achievements. Letting go of that can feel like losing a part of yourself, creating an internal struggle that stops you from fully accepting and enjoying what you’ve earned.

2. Expectations of Self-Consistency

If you believe you’re a hard worker, then starting your morning with meditation, a workout, breakfast, and a shower might create guilt and anxiety. This happens because you don't believe you can be hard-working and have time to practice self-restoration. The inconsistency between your identity and your actions will cause you to self-sabotage.

3. Guilt and Responsibility

As an entrepreneur, you feel a strong sense of responsibility towards your business and your team. Putting yourself first can make you feel guilty, like you’re neglecting the “shoulds”. But that's just not true.

4. Control and Trust Issues

Delegating tasks and trusting others to manage parts of your business can be challenging. The fear that things will fall apart without your constant oversight can stop you from stepping back and enjoying yourself.

5. Subconscious Sabotage

Deep-seated beliefs about how much you “deserve” success and happiness can lead to self-sabotage. You unknowingly create obstacles that stop you from living the ideal day you’ve worked so hard to get.

My client said to me, "I'm not sure I've earned it yet".

So I asked him what the company was before he founded it.

"Well, nothing." He smirked; he knew what I was implying.

So I said, "Listen, I'm not saying give up on your next goals for the company, but I am asking, how is it true that you have already earned it?"

The Shift You Need to Make

To truly enjoy the life you've built, you need to shift into a new identity. Building what you want requires one set of skills and mindset, but enjoying it requires another.

It's about recognizing that taking time for yourself isn't selfish—it's essential for long-term success and well-being.

If you find yourself in a similar situation, torn between what you have always known and your ideal day, let's work together to overcome these barriers.

Book a consultation with me today, and we'll create a strategy that allows you to fully enjoy the success you've achieved.

Your ideal day is within reach, and most importantly? You deserve it.


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