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Challenges of Entrepreneurship: 10 Cold, Hard Truths You Need to Know About Before You Hit the Big Time

A lot of entrepreneurs think they need to hustle and push and burn the candle at both ends until they get to the high 6 or 7-figure income mark in their business…

And when they get there, they’re done!

They made it to Easy Street, so they get to sit back and relax, because everything’s going to be smooth sailing from here on out.

I’ve been in business for 12 years now and there’s something I’ve come to understand on a deep level, something a lot of people don’t see (or don’t want to see!)…

Success isn’t the absence of problems. Success is permission to have bigger problems.

One of my mentors likes to say, “New level, new devil!” and it’s 100% true.

And I wish someone had warned me that challenges and obstacles don’t magically disappear when you get to higher levels of success in your business.

So in today’s post I’m sharing everything I wish someone had told me back in 2011 when I was starting out.

It’s basically a behind-the-scenes look at what really goes down and what you can expect when you hit higher levels of success as an online entrepreneur.

Here are the 10 biggest problems faced by successful entrepreneurs that you can look forward to as you scale your business.

Yes, I like to call these positive problems, because at the end of the day they’re good problems to have! 🙂

Positive Problem #1: You’ll Be Recognized Whether You Like It Or Not

As your business grows, more people will get to know you and recognize you.

You’ll receive messages, emails and texts from people who want to “just chat” or “connect” or “say hey.”

Maybe someone you don’t know stops you on the street and goes…

“Hey! I know you! Aren’t you <insert your name> from the internet?!”

The only problem with this is a lot of entrepreneurs are introverts and when introverts get a little bit famous, they can start to feel a little awkward because they don’t get to stay anonymous anymore.

The best thing to do here is to decide in advance how much of yourself you want to give to fans and followers in any given situation.

And you might find that sometimes your answer is a big fat zero.

This means that if you happen to bump into someone who recognizes who you are, you might have to cut the conversation short and let them know you’re late for dinner.

This isn’t about being mean. It’s about being smart.

When you protect your time and energy, you get to show up fully and serve at the highest level.

You get to give your best to your audience, your clients and your customers… while keeping enough in the tanks for yourself!

Positive Problem #2: You’ll Outgrow Some of Your Friends

When I first started my business online I had to let go of some of the friends I knew back in my 9 to 5 days.

I found that the more I embraced my new role as an entrepreneur, the less we had in common as they continued along a traditional career and life path.

It quickly got the point where our conversations became more and more stunted and stilted until we had nothing left to say to each other (just to be clear, I still have some friends that I have nothing in common with in terms of what we do for work so it’s not just about what you do but who you are).

But here’s the thing…

It’s super important to know when you’ve outgrown your social circle — stilted conversation is usually a great indicator — and actively look for new friends who can support who you are becoming and not just who you used to be. People who understand what you’re trying to do in your life and your vision for the future, as an entrepreneur.

My advice? Don’t wait until there’s nothing left to salvage. Stay in touch with people you know and like but don’t force friendships to continue if they’re not supporting your ongoing evolution.

Positive Problem #3: You’ll Get Way Too Many Invites

When you’re successful and well-known, lots of people will want you on their podcast /summit/live event and what have you…

And most of these invites will come from people you don’t know.

This isn’t a bad thing and I believe business is about collaboration and connection.

But reputation is everything in business and you don’t want to be in partnership with people who don’t get what it means to build real relationships and lead with value.

So don’t hold back…

When you receive an invite, ask why they reached out to you and what they’re hoping to get from your collaboration.

Ask why they do what they do and ask about their big vision in business and in life…

Go with your gut instinct and learn to tell the difference between people who want to build relationships and share value…

And those who are looking to gain fame or fortune by association.

Essentially people who want to use your reach and your name to forward a hidden agenda (usually this has to do with building their list from your audience or selling their programs to your list).

Positive Problem #4: You’ll Feel Alone

“It’s lonely at the top” isn’t just a popular saying, it’s true for many people.

As you get to higher and higher levels of success in your business, fewer people will “get” what you’re going through, what you’re up against and what you want to achieve.

And it gets a lot harder to find common ground or camaraderie with people you meet (unless you happen to be the kind of person who can create rapport with everyone, which is super rare!)

It’s why I like to say that the more successful you get, the more you need to get out there and find people who understand what you’re going through…

People who want what you want and who’ll be happy for you when you reach your goals.

I’ve found that one of the best places to connect with like-minded entrepreneurs is inside a business mastermind.

But keep in mind…

Not all masterminds are created equally and you could end up feeling lonelier than ever if you happen to join a group that doesn’t align with your values or your goals (for behind-the-scenes insights on finding the right mastermind group, check out The Ultimate Guide to Selecting the Right Business Mastermind).

Positive Problem #5: You May Get Bored AF 

When you’ve been teaching the same things and sharing the same message for years, I can pretty much guarantee that boredom will start to set in.

This might seem unbelievable to a lot of enthusiastic, new entrepreneurs who can’t imagine ever being bored with what they do.

But the truth is that boredom is a very real problem as you get more and more successful in your field of expertise because it steals your drive, energy and focus…

And it’s creative suicide.

So many successful entrepreneurs are bored out of their minds and they keep going through the motions in their business…

And the more they’re bored, the less creative they get and the less creative they get, the more they’re bored and on and on it goes.

Sooner or later, it gets to the point where they quit altogether…

Or they end up running their business into the ground (which I often see is a type of self-sabotage — they find a way to end their business just so they can create something fresh and new!)

The American illustrator Milton Glaser wrote,

“If you can sustain your interest in what you’re doing you’re an extremely fortunate person. What you see very frequently in people’s professional lives, and perhaps in their emotional lives as well, is that they lose interest in the third act. You sort of get tired, and indifferent, and, sometimes, defensive. And you kind of lose your capacity for astonishment — and that’s a great loss, because the world is a very astonishing place…” – Milton Glaser

So promise yourself right here, right now that you’ll do what it takes to keep yourself on the creative edge no matter what.

I want you to pretend you’re a “scientist” looking for ways to experiment and shake things up in your business. 

For instance, every time I step on stage to teach an event or session that I’ve taught before, I ask myself, “Where’s my edge here?” 

Whether it’s vulnerability or storytelling or performance or something else…

Then I teach at that edge so it’s never 100% the same each time.

So whatever you do, never let yourself settle into a “same sh#t, different day” mindset.

Avoid getting into a rut or routine that holds you back from experimenting with new business ideas, marketing techniques or ways of doing business.

And always keep why you’re doing what you’re doing front and center.

Positive Problem #6: They’ll Ask You to Share Your Expertise… For Free

One of the side effects of success is that all of a sudden people will start to ask if they can “pick your brain.” 

Basically they’ll ask for your expert insights and input for free.

This happens to me often and it happens to a lot of my successful clients and students.

So what do you do when someone wants you to give away your expertise? 

Decline as politely as you can and then suggest that they check out one of your paid courses, or training programs to get answers…

And I know this might seem selfish or uncaring to some people but it’s not.

So when you resist sharing your expertise for free, what you’re really doing is valuing who you are and what you do for a living.

And by not giving away your expertise to anyone who happens to ask, you’re also respecting every single one of your paying clients and customers.

People who are willing — and happy — to reward you for your hard work and expertise.

So when you say no to ‘brain pickers’, you’re not being selfish or uncaring… 

You’re doing the right thing.

There is however one exception to the “don’t share for free” rule and it’s when you’re dealing with a network of peers who are at the same level as you in their business and you want to contribute and support them and be supported in the spirit of generosity without any financial transaction involved…

Positive Problem #7: You’ll Wonder What to Do with The $$

Something weird happened when I hit the 7-figure mark in my business…

I had a whole lot of cash coming in and I had no freakin’ clue what to do with it!

When you’re not used to seeing big money coming into your business, you can easily start to get into a place of serious self-sabotage or overspending.

And I’ve seen a lot of entrepreneurs getting stuck in fight, flight or freeze mode when they get to the high 6- or 7-figure mark.

So the ones who fight their financial success carry on bootstrapping like they did when they first started. 

They try and do everything themselves, they don’t hire and delegate enough so they become this massive bottleneck in their business (check out #8).

Entrepreneurs in flight mode “run” from their success. They pretend like nothing’s changed because at some level they know the truth…

What got them where they are won’t get them where they want to go. 

And they’re uncomfortable about moving up to the next level where they need to learn a bunch of new things that’s outside their comfort zone (like how to be a smart investor!).

And so they try to stay where they are and they don’t come up with new goals, a bigger vision or plan that’s congruent with their new financial status.

Then there are entrepreneurs who freeze. They think, “I’ve got all this money now and I don’t know what to do!” 

And they wind up not managing  their money well. They spend on the wrong things and reinvest pretty much all of their money back into their business. So instead of creating financial freedom, they end up stuck in a hamster wheel going nowhere and needing to earn more and more.

Okay so where does that leave you? What do you do when you start seeing more money come into your business?  

Stop thinking about “income creation” and start moving into “long-term wealth” generation.

Basically this means it’s time to start looking into investing your money in something other than your business…

Things like real estate or stocks.

And unless you have millions to spare (and maybe not even then!) don’t make the mistake of getting into wealth generation on your own.

Do the smart thing and hire experts that can help you get your financial ducks in a row.

Positive Problem #8: You’ll (Probably) Become a Bottleneck 

A lot of entrepreneurs start out flying solo in their business.

And so they take full responsibility for every single task and every creative and administrative decision.

But when you get to a place where you’re starting to see big payoffs in terms of audience growth, impact and income, doing everything on your own is the worst possible thing you can do.

I know because I’ve been there myself. 

It took me years to learn how to step back and let my team members take over day-to-day tasks and also whole areas of responsibility at Live Your Message, and I’m still in the process of letting go.

One of the ways I got there was to keep asking myself this question…

How do I replace myself?

It gave me the clarity and confidence I needed to create new systems and processes and hire great team members who are just as excited about Live Your Message as I am, so I don’t need to feel like I have the whole company on my shoulders.  

Something else to keep in mind…

Sometimes, feeling like you need to be fully immersed in the granular details of your business could be an ego thing.

The truth is it’s hard to come to terms with the idea that not everything has to pass through you and it’s even harder to exorcise your inner control freak (which you needed in order to achieve success in the first place).

It takes deep humility and courage to let others take care of the things you don’t need to do so you can focus on your superpower, whatever that happens to be.

It’s all part of being an ambitious entrepreneur and if you’re committed to success and if you want to go for bigger goals and expand into a greater vision of what’s possible for you and for your business…

You need to be okay with the fact that a lot of your time will be spent learning and working with skills that are outside your area of expertise.

Positive Problem #9: You’ll Need Lots of Different Skills

Maybe you’re a rockstar copywriter, maybe you’re an awesome website designer or an energy healer or coach…

Whatever your area of expertise, it’s important to know that building a successful business means doing a lot more than practicing your core craft.

For instance if you’re a life coach, you’ll need to get good at growing your audience, and marketing and leadership. You might need basic technical skills like setting up a group call or creating new pages on your website.

And as your business continues to grow and expand you might be pulled farther away from your craft — the original thing that you loved, the thing that inspired you to start a business in the first place.

Just to be clear…

Adding a lot of new business skills to your skillset doesn’t mean you’ll have to give up practicing your core craft. 

It just means you need to get honest with yourself and figure out just how far you want to go and how much you want to scale your business.

And you need to understand that every phase of growth has its own demands around what you need to know and do and learn as a business owner.

Positive Problem #10: They’ll Say You’re an A$$hole

Some people will get triggered by your success. Guaranteed. Especially during a time when so many people are struggling. 

I’ve found that most of the mean comments or name-calling that’s come my way has to do more with the other person than it does with me.

And I’ve realized with most people, it has nothing to do with anything I’ve done or anything anyone else has done to them but how they read into things.

For instance, I had someone who attended my Message to Money Live event via livestream (online) and she told me she LOVED what I had to teach.

But then she saw people joining our Mentorship Program and receiving their welcome scarves. It was our way of recognizing and celebrating them and also so they could recognize and celebrate each other.

This woman got super upset and said that I was “dealing in shame” because I was “separating” the new students from everyone else when that was clearly not our intention… it was her insecurity projected onto me so I became the “bad guy” in her story.

People may also get triggered when you say “no” (see #6) and as Warren Buffet famous said, “Really successful people say no to almost everything.”

My advice? Don’t let them get to you and definitely don’t let them stop you from doing what you’re here to do…

And, Yes, It’s All Worth It… 🙂

When you get clear on your vision for your business, when you stay in integrity and commit to serving at the highest level, when you continue to do great work …

The voices of those who love you — clients, customers and students who want to see you succeed — will get to be a LOT louder than anything the haters can say.

And in time, you’ll learn to focus on serving people who love you and your work and you won’t give a second thought to the insults, or catty comments and remarks that used to keep you awake at night.

The truth is becoming a success isn’t the hardest thing you’ll do…

The hardest thing is to hold on to that success while staying true to your values and who you are, who you want to serve, what you want to achieve in your business and most of all…

Why you’re doing all of this to begin with.

Lots of big name entrepreneurs lose sight of why they do what they do and this is one of the fastest ways to heartache and burnout.

So let your “why” lead you forward and if you want to realize your full potential and have a great time on the way, commit to embracing the reality of success… 

The good, the bad and the ugly.

Because — when you do — you’ll realize that there’s a lot more good than bad and ugly. 🙂

Your turn…

Which of these “positive problems” listed here surprised you the most? 

Share your thoughts in the comments below. I read and reply to each one 🙂

But before you go…

Are you ready to build a business that stands the test of time?

A business that gives you the life you’ve only dreamed of?

Then, you need to discover your True North Business (the one you’re meant to build).

And that’s what you’ll uncover in my free, 60-minute Masterclass — Discover the Business You’re Truly Meant to Build & How to Share It With the World

So if you’re ready to build a business on a rock-solid foundation — instead of one built on sand — save your seat!

Love it? Hate it? Let me know...

  1. Mike Ellis Avatar
    Mike Ellis

    I’m getting ready to start an online business to show people how to reglue their furniture and antiques.
    I am 67 years old and looking to blend the brand new with a very old

    1. Marisa Murgatroyd Avatar
      Marisa Murgatroyd

      Awesome Mike! So glad to hear you’re moving forward on your dream… xoxo

  2. Jesse Carrie Avatar
    Jesse Carrie

    Thank you, Marisa, for the wealth of wisdom and honesty here. Impressive.

    1. Marisa Murgatroyd Avatar
      Marisa Murgatroyd

      You are welcome Jesse! Every light has a shadow for sure and I believe it’s important to share the good, the bad and the ugly to help my tribe have a more grounded understanding of this wild entrepreneurial journey that we’re on… 🙂 Of course I wouldn’t change it for anything!

  3. David Avatar

    Marisa this is really insightful. I didn’t realize how much loneliness and boredom would affect me, especially not having people who really understood what I was doing. Not making time for my family and friends was also an issue, and the combination put me in depression and I didn’t understand why.

    Especially being that the business was 80% automated, It made me look like at a successful ongoing business like who cares, and almost wishing it would end, so I could get back to something really exciting.

    And I didn’t fight for it enough and I realize it now. But this information gives me an idea of why I chose that line of thinking. Thank you

  4. Donya Fahmy Avatar
    Donya Fahmy

    Great piece and insights! Thanks for sharing.

  5. Jim Brown Avatar
    Jim Brown

    Thank you for the extra wisdom you share beyond your course. Nearly 87 and had to look up the meaning of AF. Sheltered life, I guess! Noticed your 1/4 inch in height now and in the past. Understand it perfectly since I was 6’3″ when I was younger but still cling to that definition as I have aged and shrunk.

  6. Muryani K Avatar
    Muryani K

    Thank you, Marisa for writing this! I’ve started seeing some of the things you wrote here happened to me (the more common one is asking to “pick my brain” and people who keep on asking for more but don’t give anything back in return). And I believe there will be more challenges in the future as I continue on in my journey. Reading this made me feel like I’m not the only one experiencing this. Thanks again for sharing!

  7. Chidiadi Wisdom Avatar
    Chidiadi Wisdom

    Much Revealing And Insightful, thank you ma

    1. Shannon Goodell Avatar
      Shannon Goodell

      Thanks for reading and for your feedback, Chidiadi! Marisa greatly appreciates it 🙂

  8. Kim Chatman Avatar
    Kim Chatman

    Marissa I added a comment but don’t know if it came through.

    1. Shannon Goodell Avatar
      Shannon Goodell

      Hi Kim, this is Shannon from Marisa’s team. I don’t see the comment… can you try again? We’d love to read it! Thanks!

  9. Criselda Avatar

    Thank you for this article, Marisa! I am saving this one for future reference. I am beginning my entrepreneurial journey as a podcaster. I would say that the ones that bother me the most are problem #1, because I’m an introvert and problem #10, because I don’t want to hear anyone’s backlash. A situation like that is what makes me want to stay in my shell. Out of curiosity, how did you handle that insecure woman who got upset about the scarves (although yes, I understand the scarves wasn’t the root issue)? What do you say to a person who responds like that to you?

  10. paul r oy Avatar
    paul r oy

    Please tell me more

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