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The Curse of the Entitled Entrepreneur

I have the exquisite privilege of seeing hundreds of entrepreneurs building their businesses each year and if I had to pin-point the biggest problem or reason people aren’t successful faster, it’s this:

Most people don’t know what their ACTUAL problem is, so they are solving the wrong problem.

I had this exact experience with weight loss. I THOUGHT… actually I didn’t just THINK, I KNEW the problem was that I was fat. And I knew the solution was I needed to EAT LESS and EXERCISE MORE. So, when I wasn’t eating less and exercising more when I knew I SHOULD be, I identified the problem as this:

“I need a NEW weight loss plan and this time stick to it.”

If I didn’t stick to a plan, I assumed the plan was bad and I found a new plan. Here are some things I tried:

– Low-Carb
– 6 small meals a day
– Juice fasting
– Lean Cuisines
– All Raw

I figured it would be easier to have the self-discipline to stick to a plan, if I found a plan that was right for me. I’d find something new to try and I’d hope this NEW thing would work and that I’d stick to it. But it didn’t.

Every plan left me hungry and unsatisfied, so at some point, I’d lose my self-discipline and I’d overeat. I’d research a better solution – a better plan for me.

You’ve seen the ads…
“Discover the Science Beyond the Plan that’s helped Millions Lose Weight and Keep it off!”

YES! YES! I want to know the SCIENCE! Give me the SCIENCE!

The next plan was always one where you would never be hungry and unsatisfied. “YES!,” I’d think, THIS is what I need. If I could find a diet plan where I wasn’t hungry and unsatisfied I would stick to it – or so I thought!

I found dozens of plans… I think I found all of them to be honest… and I would never stick to them. DUMB PLANS!

Looking back, I can see what was really DUMB wasn’t the plans… it was MY THINKING. The problem was NEVER the plans… the problem was the entitled thought I should be able to lose weight without feeling hungry or unsatisfied.



That was me… I thought I deserved to lose weight without feeling bad. Of course this was ironic because I was feeling bad about being overweight all the time!

Why is hungry and unsatisfied the worst thing I could feel? How about fat and uncomfortable? That is so much worse than hungry and unsatisfied. What no one told me (until I met Brooke Castillo) was that I should just learn to feel hungry and unsatisfied and be okay with that. No 300+ lb person in America died of being hungry and unsatisfied. (Obviously, I’m not talking about hungry because you can’t afford to eat. This was not an issue of poverty.)

How fucking entitled was I thinking I should be able to lose weight and not be uncomfortable! Where the hell did I get that idea? And what was so terrifying about being hungry? I mean the truth was, I was willing to be fat, to not fit in seats, to have to pay extra on planes, to lose out on jobs and opportunities, to dread going to movies or sporting events… clearly, I was willing because I was doing it. But I wasn’t willing to be hungry.

The PROBLEM was NOT that I needed a better plan I could stick to.

The PROBLEM WAS that I needed to learn how to feel uncomfortable and unpleasant feelings instead of avoiding them.

I had the problem wrong which is why it took me over 20 years to solve the damn problem!

Now I watch this unfold with entrepreneurs DAILY!

The first step to solving ANY problem in your business is KNOWING what the problem is. They think their problem is “I need more clients.”

This is NOT a problem! This is 2-6 problems but bundled into one, unsolvable, Gordian knot.

The trick is to ISOLATE the problems, start with one, and solve it. Whichever is the biggest problem when you separate them is the one you solve first.

Good News: It’s actually quite straight forward when you do it this way and no problem on its own is actually that hard to solve.

– Awareness (how people hear about you and the problem you help people solve)
– Lead Generation (how people raise their hand to show they have that problem)
– Sales Conversion (how people go from knowing you and liking you to trusting you with their money)
– Having powerful products that get results (how you solve the problem for your clients)
– Delivering your offer (how you build a business with sanity)
– Managing the drama (how you sabotage yourself from doing any of the 5 business building steps above effectively and with joy and ease)

The first five items on this list – awareness, lead generation, sales conversion, product development and product delivery – are the entrepreneurial equivalent of eating less and exercising more. It’s true – you will need to do them. Those are just the required steps.

But like me with dieting, what I see most new entrepreneurs do is to try to solve these problems with a new plan. One they can stick to!

Let me be clear: The problem is almost CERTAINLY not the plan.

I know with my clients I hand them the plan and all the evidence the plan will work early on in our relationship. “Here’s the plan! Huzzah!”

The problem is they think there is a plan out there where they won’t feel any discomfort. Just like I wanted the plan to eat less and exercise more without every feeling hungry or unsatisfied.


The key is to learn to feel the entrepreneurial equivalent of hungry and unsatisfied. And no know feeling those negative feelings will absolutely, positively NOT kill you!

Learn to feel scared, embarrassed, unsure and do it ANYWAY. Learn to develop a product in front of your client’s eyes before you have it figured out. Learn to figure it out by DOING it instead of thinking about it. Learn to be uncomfortable on the regular. Learn to let go of the entitled dream that you can build a business without feeling negative emotions.

Negative emotions are just part of life. It’s not supposed to be easy. And if it were easy – that wouldn’t even be fun. Think about it.

I know for me doing hard things makes me feel alive and proud myself. I love doing hard things. I love being willing to suck. I love knowing there is no way to get it right every time. Otherwise the game would be no fun.

Most entrepreneurs are like me when I was struggling with my weight. They want to find the right plan, so they keep changing their plan to one that “feels” right. They will know it feels right because it’s EASY to follow.

The problem they are trying to solve is the WRONG PROBLEM.

The problem they need to solve is: “How can I do the next step on the plan I have even though it doesn’t feel good?”

I call this problem – “Managing the Drama.”

My real problem with my weight was not knowing how to feel hungry or unsatisfied or all the other feelings I didn’t want to feel. Eating was like filling a jar – the more it was filled, the less space those was for those feelings to creep in. It would have been a great plan, if it worked.

Do you ACTUALLY know what the problem is with your business?

Are you 100% SURE you are solving the RIGHT problem?

I can give you a hint. If you have tried 3 or 4 or 5 different plans and they keep failing and your plan is to find a plan that works…. I can ASSURE you the problem is NOT that you have the wrong plan.

Your problem is that you have the entitled belief it should be easy and it should feel good.

What if that’s bullshit?

What if it should be hard and it should feel bad at least 50% of the time?

What if you knew:
– The plan I have is good enough.
– I’m going to feel bad at least 50% of the time.
– This is going to be hard.

What if that was locked in?

What would you be doing differently?

Would that make having a full-time job seem more appealing?

The best advice I ever received from my coach was this: “Stop trying to make it easier.”

You know what? That made it a WHOLE lot easier.

5 thoughts on “The Curse of the Entitled Entrepreneur”

  1. I’ve had a dream for a long time, so long it feels already like a lifetime. I bought several programs to assist me with my dream, but I was already too comfortable & afraid, so I didn’t take any action.

    I began to shift my fears into fuel. I began to embraces change. I intended upon being surroundedbya large body of water to enhance my intuition. I intended upon a more forward & creative population to embody the energy around me as an empath. I needed more moisture, a diverse population, and an unknown education nearby.

    I left comforts in places that people dream of living & came to the LAST place I thought I would ever live.

    I have come through a tremendous void of not knowing, and made myself quite uncomfortable with bigger learning curves than I imagined in one of my fields of mastery. It has NOT been easy.

    I’ve already grown in volumes from the complacency that once stagnated my growth.

    My action steps brought me beyond more than one lifetime of post traumatic stress – and it was one of the scariest things I’be ever done.

    I am exactly where I need to be, and I am embracing exactly what is allowing me to grow into my becomingness.

    I have now an even grander flame of passion warming me with greater light & rainbow sparkles that I’ve never seen. I am a delicate wildflower growing through the pavement with whispers from an inner guide.

    I am content in knowing that I am infinite & endless, like a sequoia pressing to its edges becoming more of myself! Wahoo!!!

    We are so happy that I am now awake & moving toward the successes of my higher self, guiding through my enormous heart platform, leading my body self to exactly where, who, & why we need to be.

  2. Interesting … what if we were to trust it would be easy and fun? Personally I have found that when I step back from the drama and trust that the universe has my back and that everything will happen in the perfect time and space, things seemingly fall into place. When I worry, when I push, when I plan for things to go wrong … well, the shit hits the fan. Then I step back, laugh say thank you and play with trusting. I state clearly what I want and let it go and inevitably it begins to unfold … well, until a part of me that habitually runs with old programming begins to worry. What I like best about this post are the last two sentences … that rings true. Just what of it is true? About that I will remain forever curious. I suspect that when we try to decipher what it is that is working, we collapse the waves of potential possibilities. You know, anything is possible. It’s like when we get a diagnosis of a disease … we collapse the waves of possibilities for what it is our genius body and all that is might make of the current information. Often times less effort is brilliant.

  3. I’ve found everything I’ve done in life hasn’t been easy and when I’ve accomplished my goal, I reflect on the hard work I put into reaching my goal. Example: Getting your home ready for the holidays, knowing guests will be coming, after changing the linens, scrubbing the toilets, waxing the floors, dusting the furniture, putting the decorations in place, preparing the menu, you see and feel All the emotions and hard work you had to experience and the expression on your guests faces when everything has been wonderfully executed.. What an awesome feeling.

  4. Angela,
    Thank you for this!!! Man I’m sitting here in my rabbit hole of anxiety and frustration doing your process, (which I know is correct or I wouldn’t have invested money I don’t really have right now), which was a HUGE decision! I know what you offer is right! I am so into the uncomfortable and get to see how I self sabatoge – which takes back to my feeling like shit again! However that being said…..this woke me up, again and Ilistened to this meditation today – I heard loud and clear……MY TIME IS NOW!!! So I’m on it and moving forward in my uncomfortableness- which validated I am out of my fucking comfort zone and gonna love this process!!!

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