Overcome Your Entrepreneurial Fears: Stories from People Who’ve Done It

You’ve done it. You’ve decided to start your own business and quit your job. Congratulations!

Even if you’re one of the lucky ones and have enough cash stockpiled for a decent “runway,” you probably still feel a twinge of fear and uncertainty around your decision despite your confidence in your obsessive work ethic and ability to focus.

You’re scared out of your mind. But it’s OK. You are not alone.

Remember you chose the path less traveled for a number of good reasons. You want more control over your schedule. You desire more autonomy. And you are sick of working yourself to the bone to make someone ELSE rich.

So then why are you waking up at 2 AM flooded with thoughts like…

Is my business idea sound? What if I run out of money? Is the niche I’ve chosen too crowded? Do my friends and family think I’ve lost my mind for giving up a steady paycheck and benefits? Will I have enough customers or clients to keep afloat and pay my bills?

What separates those that go on to become successful entrepreneurs vs. those we call “wantrapreneurs” are a few battle-tested beliefs, habits and systems.

While their resolve may be tested along the way, they now have their failsafe in place ensuring that they’ll never be down for long.

So, what do they do differently than the other 85% of businesses that fail in the first few years?

That’s what we’re about to show you, illustrated by real-world case studies of some of the most successful small business owners that we know. They generously offered up their insights, strategies and mindset hacks that have been instrumental in their success.

[tweet_box design=”default”]Fear is always there. It’s whether you let it stop you or use it propel you forward. [/tweet_box]As you’ll see from the entrepreneurs featured below, they took their fear and used it to be better.

Lesson 1: Overcome Devastating Setbacks

Meet Hal Elrod, or “Yo Pal Hal” as many know him, of MiracleMorning.com. Hal is a special kind of person, someone that leaves a remarkable impression on you once you hear his story.

In 1999, an almost fatal accident forever changed the trajectory of Hal’s life:

“I don’t recall seeing the headlights of a massive Chevrolet truck coming directly at me. In an instant of perverse fate, the full-size Chevy pickup, traveling at an estimated 80 miles per hour, smashed on into my undersized, and under-matched Ford Mustang.”

The metal frames of our two vehicles collided—screaming and screeching as they twisted and broke. The Mustang’s airbags exploded with enough force to render us unconscious. My brain, still traveling at seventy miles-per-hour, smashed into the front of my skull, destroying much of the vital brain tissue that made up my frontal lobe.”

The pickup hit Hal’s Mustang head on, and the force of the crash shoved the car into the lane to Hal’s right, exposing the driver’s side to the car following behind him. A Saturn sedan, driven at the time by a 16-year-old, immediately crashed into Hal’s car at 70 miles per hour.

Clinically dead for 6 minutes, Hal was in a coma for 6 days and spent the next 7 weeks in recovery and rehab in the hospital. Hal recalls lying in hospital and thinking:

“Coming to grips with my new reality wasn’t easy, and at times I couldn’t help but wonder—why did this happen to me?”

Having been given a second chance and firmly believing that everything happens for a reason, Hal decided to pursue his dreams. Sharing his life lessons with others started him on the road to speaking and coaching. And in 2006 his first book, Taking Life Head On: How to Love the Life You Have While You Create the Life of your Dreams, was published.

Instead of falling into depression and self-pity after the accident, he opted to face his fears head on:

  • He embraced how things were, rather than complaining and focusing and how things should be
  • He chose to focus his energy on making the best of what he had, rather than wishing his life was different, wishing bad things didn’t happen
  • He focused on moving forward, rather than looking backwards at the past

He chose to be genuinely grateful for all that he had and took responsibility for creating what he wanted.

But it wasn’t all plain sailing. Despite his accomplishments as a success coach, best selling author, and top salesman, in 2007 Hal’s life fell apart again. The US economy crashed and Hal’s coaching clients dwindled, cutting his income in half. He was $425,000 in debt and hit rock bottom.

Hal spent a year in misery before confiding in a friend about how he was feeling. His friend asked if he was exercising… which he wasn’t. He started running in the morning and through this, began to develop his own Miracle Morning routine. This lead to the creation of his bestselling book, The Miracle Morning: The Not-So-Obvious Secret Guaranteed to Transform Your Life… Before 8am!

Hal is once again a successful author, speaker and coach and continues to tackle life head-on. You can learn more about him by checking out his website: http://halelrod.com/.

Lesson 2: Build a Great Team

When it comes to leading, delegating and outsourcing in a business, not many entrepreneurs do it better than Elisa Doucette.

Elisa made a name for herself in recent years with her widely-read Forbes column. Last year, she launched the podcast “Writers Rough Drafts,” featuring some of the most notable writers on the planet. Yet, she’ll be the first to tell you that she got her start by taking on the Tropical MBA and its exclusive membership community as her first high-profile client.

She spearheaded the project of creating a thriving community of Internet entrepreneurs called the Dynamite Circle. They grew quickly, thanks in no small part to Elisa’s expertise.

She helped build the thriving paid-access online community of Internet entrepreneurs (The “DC”) from scratch. Due to her vision, skills and unrelenting commitment, The Dynamite Circle grew from 15 initial members to well over 1,000 in just a few years.

She curated the best content and served as official community manager, ensuring the highest levels of quality, while delivering insane amounts of value possible to paying members. She took the lessons learned from her early success and ended up applying them to her own book launch consulting and copyediting business. She has become a poster child for success through building a talented, cohesive team.

We asked her a few specific questions about her life and business over the past five years, and here is what she shared with us:

What made you decide to leave the traditional path?

“I left the traditional career path because I am an exceptional employee. I know, that sounds weird. But the truth is that I have been pivotal in the success of multiple startups and corporate departments, often tripling sales revenue and crushing goal projections with my tenacity and expertise. “

Elisa freely admits she craved freedom above all else. She hated being tied to a set schedule, regardless of what she achieved. On a whim, she started her own freelance copywriting agency and landed her first paying clients.

No stranger to the fear of failure, Elisa readily admits to occasional anxieties around her business. However, unlike most people, she channels the fear as fuel that drives her to act.

She says, “I’m hugely anti-failure. I was so motivated to ‘prove’ to people that I was, in fact, able to execute these solutions and ideas on my own.”

We listen to Elisa because she walks her talk. Her successes are inspiring and have given us the courage to go after what we want as well.

What’s the ONE tip you’d give to any entrepreneur?

“Learn how to delegate.

My energy is best spent figuring out how to use our available resources to manifest the vision I have for the company. It isn’t best spent setting up Google Documents or chasing people for payment. So I find people better at these things than I am, and happily entrust their completion to my team.”

Lesson 3: Build Influential Relationships

80% of the people in Mike Harrington’s life—coworkers, family and friends—told him it was too risky. Many actively tried to talk him out of going for it. Yet, he chose to trust his instincts and work ethic, and got on with it. He took the leap from his six figure corporate gig and jumped into entrepreneurship with both feet.

Mike took action. Here’s what he accomplished in under 12 months:

  • He aggressively saved money (lived on only 25% of his take-home pay) in order to pay down remaining debts and to stash an “escape fund.”
  • He learned how to find, pitch and land freelance copywriting clients, which was both scary and exciting. As a result, new opportunities dropped in his lap – because he put in the work with an almost obsessive focus.
  • He ponied up the cash and bought a one-way ticket to South America. There he was able to take advantage of the cheaper cost of living.


Mike has seen success with his own two eyes – due to an unrelenting work ethic – and it’s only added to his conviction and motivation to make all of this work. He explains:

“I got my feet wet by landing freelance copywriting and SEO work, while keeping up appearances in my corporate job. I moved on to selling affiliate products and services that I believed in. Once I found that I could indeed make enough money to get things rolling, my confidence took off.”

[tweet_box design=”default”]Relationships precede success.[/tweet_box]

Relationships are the lifeblood and currency of your business. Relationships mean more referrals, better advice and a built in support network to weather the storms.

Key relationships with influencers can enhance your authority status in your niche. They can propel you from the lower ranks of Internet obscurity into an authority in your niche.

There is a caveat: Create as much value for others before asking for anything in return. Whether it’s your clients, partners or the influential people you meet along the way, people tend to remember those that offered help.

In the game of online entrepreneurship, relationships and reputation are your currency—especially in your first 12 months. Remember, negative talk can and will spread like brushfire. Your reputation can be tarnished faster than you can say “Wi-Fi.”

Lesson 4: Take Action

Lise Cartwright of OutsourcedFreelancingSuccess.com says:

“If you want to lead a life that gets you excited to get out of bed each day, then you must commit to doing whatever it takes to make it happen. That means you face fear head on and bounce back from setbacks as fast as you possibly can.”

Action trumps all.

Here’s what Lise achieved in less than 6 months after quitting her full-time job:

  • She used skills she already had in order to replace her full-time income. Her main focus was freelance writing, working with clients on sites like oDesk, Elance, and Freelancer.
  • She went on to scale her business as quickly as she could, finding clients interested in long-term work, and then outsourcing that workload to contract writers she hired. Long-term clients are easiest to find once you’ve already built a trusted relationship with them.
  • She co-founded a Mastermind group of like-minded entrepreneurs to stay sane and have other people understand what she was going through. As a result, the entire group bounced back from setbacks quicker and stronger.

Lise learned quickly that the ups downs, and periods of self-doubt will always be there, lurking in the shadows. But the antidote to these underlying fears comes in two simple words:

Imperfect action.

Have you experienced this on your journey?

People around you may begin to offer you unsolicited, often unhelpful advice. This can be annoying, but when you expect this to happen, you’ll be better prepared to handle objections and even negativity with ease.

When you take a step in the direction of doing what you love, the Universe will test you. But if you stick to your guns, unseen forces will begin to guide you, and you can’t help but start to succeed. The quick wins will breed momentum and confidence in the path you’ve chosen.

Remember: the test is in your own resolve and a burning desire to lead a life you’ve designed, instead of following someone else’s design for you.

There is no magic pill to solve all of the challenges you’ll face as an early entrepreneur. However, if your eyes are wide open, you develop new skills and nurture powerful relationships, a great thing can happen:

You’ll realize that while you might be in business by yourself, you don’t have to be alone.

What’s In It For You?

If you remember nothing else from this article, remember this:

Success leaves clues.

When you see what systems, habits and tools are working for other successful entrepreneurs, patterns begin to emerge. And, once you recognize and start implementing these systems, mindsets and daily habits, the scales of success begin to tip in your favor.

Remember, entrepreneurship and walking your own path is not for the faint of heart. The harsh truth is this lifestyle is not for 95% of people, and even that’s being generous.

But, with persistence, the right tools and an unbreakable mindset, you can and will tip the odds of success in your favor. Remember to trust the process and push through the dips.

What about you? What fears do you find yourself facing on your entrepreneurial journey? Tell us in the comments below!

About Lise Cartwright

Lise Cartwright is an indie author and coach living in Auckland, NZ. She helps new freelancers and author’s get out of their own way so they can figure out what “doing what you love” means for them.

20 thoughts on “Overcome Your Entrepreneurial Fears: Stories from People Who’ve Done It

  1. Don’t outsource until you’ve started making money with your business. And, even then, proceed with caution because outsourcing is a skill and, like any other skill, it takes practice to master.

  2. “Imperfect action.” I love it! This post was worth reading for that one tidbit of philosophy alone! It speaks to the many fears I experience each day in working to get my ABM business rocking. Sometimes the fear becomes overwhelming enough to freeze me in inaction. Not anymore! I’m dedicated to the idea of “imperfect action.”
    By the way, ABMers, here’s a link to a story of entrepreneurial success being born from the depths of devastation. Go to http://www.chadhymas.com and learn from this guy’s experiences, as well. Trust me…you will be blown away! You will know you too can do it.

  3. Interesting comment Tushar… I’d have to disagree though. Personally, I wish I’d started outsourcing sooner than I did, the ability to scale is largely dependant on the number of hours YOU have to dedicate to the things that make a difference in your business… you cannot do this effectively alone.

    You should always approach outsourcing in the same way that you would approach working with a client, by doing your research, making sure that the person you work with is the right fit and setting up process and procedures to back it all up!

  4. I’m glad you enjoyed that Gary, it’s definitely something that I say to myself every day. Along with taking imperfect action, as a writer, I also love “done is better than perfect” because you can spend a lot of time trying to make things perfect, when in reality, getting something done and shipped is far better than never sharing it with anyone!

    And thanks for sharing that link, checking out Chad’s site now!

  5. Good article giving insights with certain tips and keys from successful entrepreneurs on how success journey explores. Really liked on building a great team and influencing relationships. Well informed as quick snapshot summary to a new start-up like me with encouraging guidelines. I recently started my business on Strengths coaching and some of these are really useful to explore and grow. After all, I liked this sharing, loving and caring from the authors of this article. Jay Ho.

  6. I’d also have to disagree with waiting to outsource.

    Especially if you have a cash runway or are still in a job with a regular paycheck.


    How much is your time worth?

    For me, I spent MONTHS trying to figure out wordpress coding, plugins and other nonsense, when I could have hired someone online for $10 an hour to save me HUNDREDS of wasted hours.

    For me, taking a small chance on hiring someone for (relatively) inexpensive is a no brainer, and I wish I had started from the beginning.

    But guess what held me back?

    Yep. Fear.

  7. Lise hammered into my head “done is better than perfect” throughout the two months we wrote our book together.

    If it weren’t for her kicking my ass, I’d likely still be agonizing over edits in some stupid quest for “perfection.”

    Instead, I’m already on to writing my next book.


  8. Stoked you got value from this as well.

    DEFINITELY focus heavily on relationships. They really are the lifeblood of any new business, as it’s struggling to get its footing in those first 12 months.

    You can never go wrong with investing in relationships. Whatever it takes. Conferences. Events. Online communities. Helping other influential people with a skill you have.

    It’s made all the difference for me. And, I bet Lise would agree. 😉

  9. Loved this,

    Well I guess you are right about persistence, the right tools and an unbreakable mindset which will make the difference.


  10. Thanks for your support Samir and glad you liked the article! Persistence is key in achieving success in anything you really want. Giving up is not an option 🙂

  11. And, the good news is this:

    Persistence is definitely a SKILL that can be developed, as you move forward and start getting early wins.

    It’s not some natural talent some people get from birth and others don’t.

    And, it’s the #1 most common trait I’ve seen in every successful entrepreneur I know. Persistence trumps all in this game.

  12. Many thanks for an excellent post.

    I found the part about team-building and delegation most interesting. Because from the things listed, this seems to be my biggest problem.

    Imagine, I have only 100 dollars each month, which I can spend for learning to delegate. By “learning” I mean actually delegating some work to someone on Elance and then learn from the experience.

    What can I do in order to learn delegation most effectively under these restrictions (including learning to pay the minimum viable price and not the higher price you think is deserved) ?

  13. Here’s what I like to do.

    If it’s a brand new project, or something I haven’t hired for in the past, I have a system.

    1) Find my top 3 freelancers for the skill in question.
    2) reach out and offer them work.
    3) Give them a SMALL part of a project to gague their work, communication, skills. This mitigages risk on both sides.
    4) Pick the one you work with the best. If necessary, you can offer them a bit more $$ as an incentive to prioritize you.

    As you know, most freelancers (esp on fiverr.com for example) aren’t making money on price. They’re doing MASS volume. Sometimes that sacrifices quality.

    So, find someone great, give em a small bit, see how it goes, then cement the relationship.

    That’s what works well for me!

    Good luck.

  14. Hey,

    Thanks for the great read, it really opened my eyes to running my own business.

    As i say that, im scared to death of quitting my day job to start my own thing, even though im a true believer that to make real money in this world, you must do your own thing.

    Thanks for giving us who has no hope, hope.


  15. Hey Jason

    Glad you enjoyed it! Here’s a couple of things that can ease the fear of quitting your day job:

    1. Get a few months worth of savings behind you so the need for cash isn’t hanging over your head
    2. Try and land your first few clients BEFORE you quit your job.
    3. Have a plan in place – don’t quit without knowing where you’re going

    Feeling the fear, figuring out worst case scenario’s so you know what could happen helps too. For me, once I knew what the worst COULD be, I was able to plan and prepare.

    You can do it Jason!

  16. Thank you for the kind words. I have been battling it for years if i should start my own thing, and i believe it’s about time that i set my fears aside, and just do it.

  17. Hi Louis,

    A few thoughts:

    1) You’re just 18. This is great! You’re getting a much earlier start with the mindset, and taking advantage of the new opportunities in front of you. Nicely done.

    2) What you’re doing now will likely be completely different from what you’re doing in 5 – 10 years time. But all of the skills, the work ethic and the relationships you build will continue to bleed from one project into the next, and your momentum will build.

    Keep up the great work, and thanks for the comment!


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