I polled my newsletter subscribers about their top three struggles, and the results were a unique insight into human psychology.
People who make under $100K say their top struggles are:
- Procrastination
- Self-doubt (like fear, analysis paralysis, trusting themselves)
- Lack of clarity (on their purpose, strengths, direction to take their life/business)
So what do you think the top three struggles are for people who make over $100K?
- Procrastination
- Self-doubt (like fear, analysis paralysis, trusting themselves)
- Lack of clarity (on their purpose, strengths, direction to take their life/business)
On the surface, they’re the same—but are they actually?
For simplicity, let’s pretend $100K is the threshold for success (or at least a rite of passage into financial success).
•••
Pre-Success
Before you cross this threshold, these three struggles look different:
Procrastination
Procrastination comes down to living by a single word: “Someday.”
- Someday, I’ll be a writer.
- Someday, I’ll start that business.
- Someday, I’ll do that thing I’ve always wanted to do.
But one day, you’ll be out of somedays. Memento mori.
Like we talked about in How to Stop Procrastination (and The Psychology Behind Why You Do It), procrastination is often a fear-avoidance strategy—which is why productivity advice typically falls flat.
Most people want to achieve success, but only a fraction ever achieve it because very few people take action.
Ideas are easy. But ideas aren’t reality. It doesn’t matter how great of an idea you have, how much potential it has, or how much it could change your life or the world.
Because if you never take action to make it a reality, it’ll never exist.
Self-doubt
Doubt kills more dreams than failure ever will.
Whether it’s the Four Horsemen of Fear, self-sabotaging behaviors like analysis paralysis, or simply not trusting yourself and your own intuition about which direction is right for you—so many people who could otherwise succeed and change the world give up before they even begin because they’re riddled with self-doubt.
Most of the time doubt and anxiety are selfish—meaning you’re so focused on your own insecurities, you can’t see past them.
So you wait until you find the courage to take action, but courage might never come.
Instead, one thing that works better than waiting around to “find” courage is to focus on building conviction.
Conviction happens when you look beyond yourself and focus on helping others and what they need—and it’s way more effective than looking for courage.
I go more in-depth with this idea in my conversation with Pat Flynn on his Smart Passive Income podcast. You can check it out here. Pat and I talk about how we both still struggle with nerves sometimes, but by focusing on our audience, rather than ourselves, we’re able to conquer self-doubt and share our message with the world.
Lack of clarity
Thinking you’ll succeed without clarity is like trying to shoot a moving target in the dark—not only is your goal moving, you don’t even know what it looks like.
If you never figure out what you want and the specific steps you have to take to achieve it, you’ll likely forever live in the land of wantrepreneurs and daydreamers.
But it doesn’t take insane intelligence, resources, or skills to figure these out enough to cross the $100K threshold.
It mostly comes down to figuring out what you want and what you need to do to achieve it, which typically means picking a direction, committing to it, and iterating for long enough to gain traction.
Side Note: I walk you step-by-step through how to do this in my on-demand coaching course, so check it out if you want a proven system that’s helped hundreds of entrepreneurs, founders, and leaders all over the world clarify what matters, overcome what’s standing in their way, and do the work they know they’re meant to do.
But once you develop the right strategies, you’re able to cross the $100K threshold. Then you’re ready for all the challenges post-success has to offer!
•••
Post-Success
Because after you cross the threshold, these struggles take a new form…
Procrastination
Procrastination no longer means putting off starting a business—now it means putting off a meaningful life.
It means neglecting your health and loved ones, putting off pivoting your business to something more fulfilling, or continuing to not do the things you said you’d do once you became successful.
- You can’t buy health once it’s gone.
- Your kids don’t care how much you make if you’re never around.
- On your deathbed, you won’t look back on your life and wish you could’ve worked harder.
I’ve seen too many entrepreneurs who are successful on paper but absolutely miserable in reality (check out my article on Lucrative Misery for more).
At a certain point of success, the only thing you’re procrastinating is enjoying your life.
If it feels like the goal post of “enough” is always just out of reach, the only way to ever reach it is to stop chasing “more” and look around at everything you already have—often times, you’ll realize you already have “enough.”
Self-doubt
Self-doubt no longer means letting your insecurities keep you from starting—now it means letting your insecurities keep you from moving forward.
For example, I’ve worked with 7-figure entrepreneurs who’ve built incredible businesses that have helped millions of people improve their lives. Yet they themselves still struggle with Imposter Syndrome and doubt their abilities to continue to succeed.
The most common doubts I help these clients navigate include:
- What if everything goes to zero tomorrow?
- What if my audience doesn’t like the new direction of my content?
- What if my customers don’t like the new product I want to launch next?
Self-doubt is often unrealistic. But just because it’s not based in reality doesn’t mean it doesn’t affect you in reality.
The likelihood everything goes to zero tomorrow? Virtually zero. And even if it did, you’d be just fine because of the skills, network, and reputation you’ve built along the way.
The likelihood your audience hates your new content? Super low. And even if they do, you’ll simply attract new people. Your “audience” isn’t a homogenous entity—it’s a collection of individuals with individual interests. But more than anything, people follow you for you—not your content.
The likelihood your customers won’t like or buy your next product? Also pretty low. Because if you’re passionate about the product, you know it addresses a real need, and you’ve appropriately positioned it to your customers, at least a subsect of them will buy it. And if they don’t? Learn from it and iterate for the next launch.
No one has a 100% success rate in entrepreneurship—it’s about surviving and iterating.
Lack of clarity
Lack of clarity no longer means not knowing how to succeed financially—now it means not knowing which direction to take your life, what fulfillment means for you, or what impact you want to have on the world.
The biggest reason most successful entrepreneurs reach out to me for coaching is because they feel stuck or are trying to navigate existential questions like:
- “Is this it?” They’ve worked so hard for so long and thought they’d be happier.
- “What’s next?” They know they’re meant for more, but don’t know what that means for them.
- “What’s worth my time to build?” They’re ready to climb the next mountain, but don’t know which mountain is worth conquering.
In this case, clarity comes down to doing a lot of self-discovery.
Most of us spend our entire lives chasing, planning, and doing. But we never take the time to cultivate stillness, look inward, and really clarify what we actually want out of life and what’s worth our most precious resource—our time—to pursue.
The way I approach this with clients is we start by doing a lot of self-discovery work to clarify their Core Value. Then we define what a life (and business) aligned with their Core Value looks like.
Then we apply my GOLD Framework to make it a reality:
- We create Goals that progressively move them closer to a life aligned with their Core Value
- Then we identify Obstacles that could prevent them from achieving that life
- Then we develop strategies to help them Leverage their strengths and resources to overcome these obstacles
- Finally, we build systems to help them maintain the right Direction and course-correct as needed
It’s simple, flexible, and super effective.
If you want to work together, shoot me a message or check out my coaching page for more information. I’d love to help you build a values-aligned life and business.
•••
Final Thoughts
It’s easy to think that success removes all your problems and insecurities.
But talk to anyone who’s succeeded, and they’ll tell you this isn’t true—they just evolve.
Because we’re human. And humans, by nature, are kind of insecure. We struggle to take action. We struggle with self-doubt. We struggle to admit what we want (or create the space to figure out what we want in the first place).
Just because you succeed, doesn’t mean you won’t struggle. But just because you struggle doesn’t mean you can’t succeed.
True success comes down to clarifying what success means to you and aligning your actions and intentions to make it a reality.
What’s your experience been as you’ve navigated success? Are these the most common struggles you’ve had, or were there others?
I’d love to know.
And if you found this valuable, consider sharing it with your network so it can help others.
