4 Signs You’re Ready To Start Your Dream Business

On some days you are absolutely certain it’s time to chase your dream and take the plunge into entrepreneurship. But on other days the doubt and fear of the unknown are enough to make you pack your lunch and trek off to another day on the J-O-B.

The dichotomy between the two extremes (success & happiness or failure & embarrassment) leads many to a purgatory of indecision, making them apprehensive in making the final push to become an entrepreneur.

dream business

Unfortunately, there is never a perfect time to start a business. No matter how long you wait, you’ll never be experienced enough, you’ll never have enough capital, and you’ll never have zero risk. There’s always a chance that your business will fail, but there’s also always a chance that it will succeed. Just like Amazon Founder, Jeff Bezos said:

“I knew that if I failed I wouldn’t regret that, but I knew the one thing I might regret is not trying.”

Today, it’s my goal to help you chase your dream. To give you the tools and wisdom but more importantly, ask you the right questions to ensure you’re 100% ready to start your own business. Here are the 4 pillars of a prepared entrepreneur.


Pain is one of the top motivators for the human mind. While your job can be an incredible funding tool for your dream, it can also be a throbbing irritation of your soul. But when people tell me they want to start their own business because they hate their job, I tell them that’s not a good enough reason.

Starting a business requires fuel. And not just a pinch. The recipe calls for heaps of the stuff. A burning passion that’s not fleeting, but consistent. A desire for freedom, purpose, control, and meaning should be at the core of every aspiring starter.

If you chase the passion, not the money; the money will end up following you.

Here at StartupCamp, our 3 month coaching program for aspiring entrepreneurs presents not only the questions to help you clarify your passion, but the formula to translate that passion into a profession.

Critical Questions:

  1. Is your job unfulfilling even on the good days?
  2. If you worked somewhere else would that change the pain? Authentic entrepreneurs are typically unemployable, no matter what company, salary, or opportunity.
  3. What’s the driver of your passion? Is it mission, purpose, and freedom or just frustration? List off a few specifics.



The idea of a lone-wolf entrepreneur, fighting their way forward through their own genius is a lie. Successful entrepreneurship is fully entrenched in community. They are supported by their friends, family, and acquaintances. And those who dare to embark on this journey alone, will find themselves at the back of the race.

Because most of the world has been led to support and strive for an employee mentality, your bold expedition will likely cause discomfort in those around you. That’s why starters who have a supportive community, whether it’s your spouse, parents, a mentor, or just your group of positive friends have proven to not only be more successful, but they also more sustainable.

In module #2, I task StartupCamp members to post a bold declaration on social media and/or email. To ask for both support and accountability in pursuing their dream. Are you ready to share your dream? Are you ready to ask for accountability from your community?

Critical Questions:

  1. What 2-3 people would commit to supporting you on your journey of entrepreneurship?
  2. Is there anyone who might hold you back or feel uncomfortable with you doing this?
  3. Do you have any experienced entrepreneurs around you who can help navigate these new waters?



A business mentor once told me,”If you’re not willing to learn, no one can help you. But if you’re determined to learn, no one can stop you.” In the past 11 years, I have read over 200 books, enrolled in an expensive executive psychotherapist coaching course, engaged with a millionaire mentor (for 3 years), and even joined a few elite mastermind groups.

Because our education system doesn’t support an entrepreneurship mindset, there’s a lot of lost ground to be made up. But in my experience entrepreneurs learn by doing, not learning to do.

The problem is this: Too many starters drop out of college to forge the waters of entrepreneurship on their own. While I fully agree traditional school is a horrible solution for the entrepreneur, education is not. Until recently, there were no succinct and affordable courses designed to support new business owners on their trek.

That’s why last year I created StartupCamp. A 3 month experiential learning course for aspiring entrepreneurs. A place with coaching videos, study guides, PDF packs, checklists, recommended reading, podcasts, training articles, and a private community of like-minded people.

Critical Questions:

  • Are you ready to begin a 1-2 year season of intentional learning?
  • How do you learn best? Reading, listening, watching, or doing? Studies show it’s most effective to engage in as many learning forms as possible.
  • Are you able to adjust your schedule to allow for 2-5 hours of learning time per week?


As I said in the opening of this article, “Fear has kept many would-be entrepreneurs on the sidelines, while good opportunities and ideas paraded by. Most of them didn’t lack insight. They lacked courage.”

Many new entrepreneurs lack the courage to forge ahead alone and yearn for someone to take the first step, to go first, to show the way. But it could be argued that the dark provides the optimal context for entrepreneurship. After all, if the pathway to self-employment were well lit, it would be crowded.

The difference is those who succeed is confidence. While you’ll never find a business venture absent of fear and risk, you’ll also never find a successful story without a confident leader. Someone who has learned to step into the face of adversity, perform under pressure, and cast captivating vision to inspire those around them.

And it all begins with steps 1-3. (1) A confirmed overwhelming passion to change something, (2) a community who will both support and hold you accountable, and (3) an effective education plan to prepare you for the voyage. By committing to these three pillars first, the fourth will naturally follow.

Critical Questions:

  1. What’s limiting your confidence? Is it know-how? Is it experience? Is is understanding? Is it money?
  2. What’s your greatest fear? Failure? Embarrassment? Bankruptcy?
  3. What can you do to help lower those fears and increase your confidence?


If you’ve answered in the affirmative to all four signs, and are now even more convinced to take the next step, consider an educational membership at StartupCamp. We believe dreams are worth chasing. It’s our hope to support anyone looking to start their own business.



Are you ready to be an entrepreneur? What’s your dream? Let me know in the comments below.