27 Reasons Entrepreneurs Are Stuck
Entrepreneurship is the ultimate game: one where you’re on the frontlines of steering your own ship, doing meaningful work of your choosing —and if you do it right, creating a level of financial prosperity and lifestyle freedom most only dream about.
But it doesn’t always work out that way.
I’m constantly having conversations with entrepreneurs, solopreneurs and side hustlers who can’t seem to breakthrough —and are now asking themselves the following questions:
Is this really for me?
Am I capable of doing this?
Why can’t I seem to create their results?
And at some point or another, we’ve all been there. During my ten-year entrepreneurial career —I’ve been there more times than I can count.
But I’m still here, and I’m not going away anytime soon. In fact, I see these challenges and moments of adversity as opportunities to shift perspective and create new results.
Because on the other side of the challenge is what I consider the ultimate success: a life and business you can’t wait to wake up for.
In this post, I’m going to share 27 Reasons Entrepreneurs Are Stuck —and what to do about it. For each one, I’ll add some context and an action step to help you breakthrough.
Let’s get started.
1. You’ve got too much on your plate —make deletion a daily exercise.
As your own boss, it can seem impossible to say “no” or prioritize what really matters, so you do it all —until you wake up overwhelmed, exhausted and spinning your wheels. This is when the art and science of deletion and creating space becomes non-negotiable.
ACTION: Delete one thing off your plate right now. Don’t overthink it.
2. You’ve got Plan B’s and C’s —instead of being 100% all in.
You’ve got a marketing agency, a coaching business, do personal training on the side and also have a YouTube channel. Come on! This is not something special: this is holding on to life rafts and not going all in on your one thing. This takes courage, but will pay off.
ACTION: Identify what is holding you back from going all in.
3. You’re not great at being your own boss and lack self accountability.
You do realize there’s a purpose to corporate offices, endless meetings and going to lunch with coworkers you can’t stand, right? OK, maybe that’s only me. It’s all about accountability, and for many entrepreneurs —they don’t have much of their own.
ACTION: Work on this every day this week —choose a time to wake up (mine is 4:30) and don’t break it.
4. You work from home and wonder why you’re distracted and scattered.
Doing creative and purposeful work in the same place you watch Netflix and hang with the family is a terrible idea. People will argue with me about this, but I am adamant: working from home is robbing you of your results and growth.
ACTION: Find a coworking space, get an office or go to a quiet coffee shop.
5. You’re not owning your value and expertise —and charging enough.
As a freshly minted entrepreneur, it’s easy to not own your value and charge less under the guise of wanting to create momentum and case studies. But remember: what you’re an expert at is something others are blown away by —and we’re often the last to acknowledge the value of our expertise.
ACTION: The thing you’re an expert at has the potential to change lives, when will you own this?
6. You’re going after $20 or $47 customers instead of higher ticket ones.
Related to the above —it can be tempting to start a low ticket subscription model as a creator and entrepreneur. But make no mistake: marketing to the masses is 20X harder than marketing to the few in front of you. You need numbers and marketing prowess to hit the many.
ACTION: It’s tempting to fish for the bottom when you’re staring, but going after this market is HARD work for little payoff.
7. You’re believing you have to be on every social media platform.
Exhale, you don’t. I teach and train others under the model of picking a pillar platform —consider this where 90% of your effort should go. For me, it’s the Academy podcast. Commit to your pillar platform for at least 18 months, and then start branching out.
ACTION: Pick one pillar platform —where your people are already hanging out.
8. You’re not ruthless with saying ‘no’ and creating boundaries.
There’s nothing worse than someone reaching out to ‘connect’ and finding yourself at Starbucks as they blather on about randomness —and then try to pitch you something. Because entrepreneurs get paid on results, and not time invested —they must be extra diligent about what they’re saying “yes” to.
ACTION: This week, create boundaries and protect “you” time.
9. You love your brand, product or service but not the marketing of it.
You can have the best coaching program. You can have the best personal training facility. You can have the best software —but if you’re not getting it in front of people every day, you’re going to lose. Most entrepreneurs wait until they’re in dire straits to finally fall in love with marketing and sales. Don’t be that guy or gal.
ACTION: Study marketing, influence, sales and persuasion this week.
10. You’re surrounded by B- and C players who won’t demand excellence of you.
Does this person amplify my belief, clarity and possibility —or do they diminish it? This simple question is one of my favorites for identifying the right tribe of people to support my mission. Be careful who’s around you, because their mindset will become yours in due time.
ACTION: Take an inventory of your tribe —and get radically honest if they’re truly helping you.
11. You’re “rolling solo” instead of investing in yourself through coaching and mentoring.
When you invest in yourself and your business —you’re writing your dreams a check. You’re pouring your attention and energy into yourself. Nothing will replace this. Every entrepreneur must work with someone —whether it’s a virtual course or program or a 1-1 mentor. The stakes are too high not to.
ACTION: Invest in a course, mentor, product —something that helps you with your blind spots.
12. You’re unable to navigate the emotional stress that comes with entrepreneurship.
All transformation is emotional. I’ve said this on the podcast and in my books countless times. Leaving your comfort zone requires you to brush up against your emotional edges —and face fear, doubt, uncertainty and stress.
Whether it’s launching and shipping your product or hiring your first employee, entrepreneurship is the arena where you get to face yourself head on.
ACTION: Journal when you’re going through a tough time, this is a great practice for emotional intelligence.
13. You’re playing the comparison game to everyone’s highlight reels.
Comparison can either crush your momentum or fuel you to see other’s success as proof that yours is possible too. But be careful, because subconscious comparison can lead to self-sabotage, despair and feeling more stuck than ever.
ACTION: Stop doing this and understand they’re going through hardships like you are.
14. You don’t know who you’re speaking to —so you speak to everyone.
You’re not for everyone. Southwest Airlines is not for everyone. Apple is not for everyone. Starbucks, even with 28,000 locations —is not for everyone. Be for someone. Stand for something. Be bold, audacious and specific. Otherwise, you will get lost in a sea of mayhem and uncertainty.
ACTION: Who are you speaking to, what are their aspirations? Where do they hang out? What keeps them up at night? Drill, drill, drill.
15. You haven’t fallen in love with your sales process and made bold offers.
“But Tommy, I don’t want to come across that way.” A health coach was telling me the reasons why she couldn’t pitch her services —until I asked her about where she got her certification, knowing it cost her a tuition of $8,000 and inquired about the sales process.
“What? There wasn’t one…it was amazing!” And that’s my point —when you’re aligned in the people you’re serving, there seems to be no sales process. They want what you’ve got and it can help them, so there’s a value exchange. The drama around sales is killing most entrepreneur’s potential.
ACTION: You’re already selling every single day —get rid of the drama and fall in love with sales.
16. You think marketing means posting on social media.
I’m looking at you, thought leaders and coaches. You spend 90% of your time on social media and say you’re “working.” Marketing is not social media, it’s systems, processes, referrals, email marketing, landing pages, sales pages, VSL’s, offline marketing, upsells, sales conversations, etc.
ACTION: Social media is 10% of marketing —what is the other 90% you’re neglecting?
17. You’re consuming way too much —instead of creating.
If you’re not starting the morning on your terms and doing your most important creative work —you’re going to lose. Aim to keep your creation at 75% and consumption at 25%, not the other way around.
ACTION: Don’t consume anything until you’ve created every single morning.
18. You believe you’re “one big break” away or waiting to be discovered.
This illusion holds so many people back from doing the messy work in front of them —with the hopes that one introduction or call will change everything for them. It won’t, and is a lazy way to play in the game of life and business.
Oprah is done building careers, and the Today Show doesn’t need you. Instead, be the linchpin and create your own empire.
ACTION: Seek mastery, play the long game and understand everything takes reps.
19. You don’t believe in calendars and think free time equals freedom.
I’ve drilled this down a ton on the blog and in my podcasts —and even created a course based on the concept. You can grab 7-12 Formula: One Year’s Worth of Results right here —and ensure you get the real freedom most business owners are only dreaming of.
ACTIONS: If you’re not using a calendar, you’re already losing.
20. You’re waiting to feel ‘inspired’ to create —so you lack consistency.
I wrote most of my books at 4:30AM in the morning in an empty downtown Phoenix office. Most of my posts are written under less than ideal circumstances —but I’ve trained myself to execute regardless of how I feel. You must do the same, otherwise you will always be held hostage by your “feelings and moods.
ACTION: Be the person who creates when they’re exhausted, uninspired and swirling in self doubt.
21. You haven’t sold yourself on your brand, product or service.
Start with one sale, one fan, one admirer, one consumer: you. If you don’t love your content, brand, product or service —something is missing and you can never expect someone else to. Watch your videos, use your software, take the nutritional supplements you’re selling others.
ACTION: Sell yourself first. Be your number one fan. Fall in love with what you have to offer.
22. You’re not working on your money mindset and make decisions from scarcity.
We all have a money mindset: stories, beliefs and narratives passed down from family, relationships and culture. None of them are inherently ‘good’ or ‘bad’: they’re either fueling our growth or holding us back. For many entrepreneurs, including myself —they must make the shift from scarcity to abundance when it comes to their money mindset.
ACTION: Identify the money mindsets and patterns holding you back from your dream income.
23. You’re not identifying and acquiring key skills on a weekly, monthly and quarterly basis.
Without acquiring valuable skillsets in your business as an entrepreneur —you will stay stuck. Skill acquisition is not random, it’s not dabbling and done only when you feel like it. It must be identified, prioritized and scheduled —or else. I wrote about this in both of my books: The 1% Rule and the Leap Of Your Life.
ACTION: Identify and block out the core skill you’re working on this week —if it’s not scheduled, it won’t happen.
24. You’re wasting your most precious energy and attention on the small, random tasks that don’t matter.
There’s tons of people who create a powerful morning routine to achieve peak clarity and energy —and then scroll on social media. The truth is only 20% of your efforts are going to lead to 80% of your results. The key is doing less, while achieving more and to stop being busy…being busy.
ACTION: Define ‘winning’ the day and do the ONE thing that moves your business forward.
25. You’re not training your mind, body and spirit every single day and creating peak states.
As entrepreneurs, our emotional state will determine our consistency and follow through. We must have powerful routines —in the morning, sprinkled through the day and to close out the evening to ensure we’re finely tuned.
ACTION: Spend at least 45 minutes before sunrise working on yourself. This is the time the champions rise.
26. You’re not shipping and launching before you feel ready.
It will never feel complete, and you’ll always want to tweak some things. But perfectionism is fear disguised —and will always hold you back. Standards matter, but at some point: you’ve got to put yourself out there and ship.
ACTION: 80% is good enough —ship, ship, ship and then ship more.
27. You don’t have an unbreakable, unshakeable, emotional ‘why.’
The last one may be the most important: getting clear on why you’re doing what you’re doing in the first place. Because the road of being an entrepreneur means sacrifice: early mornings, late nights, emotional battles, questioning your path and getting to know yourself. Without your why, you will fold.
ACTION: Dig deep on your why through meditation, visualization or journaling.
27 Reasons Entrepreneurs Are Stuck
I wrote this list in hopes of helping you out as a creator, entrepreneur and business owner.
I’ve personally experienced every part of this list —and have learned valuable lessons. I wouldn’t trade what I get to do for the world, even if it can be daunting and tough at times.
If you want more help, make sure to grab the Integration Experience audio training on the front page of the site, or one of my books where I expand on the above and give you real world, tactical tools to use.
I’m curious: which connected with you most and what are you committed to doing about it?
