How To Overcome Challenges & Obstacles As An Entrepreneur

Tim Sullivan
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As a Membership Advisor at Strategic Coach, I help entrepreneurs understand how to overcome challenges, transform obstacles into opportunities, and tap into their own unique strengths. This allows them to determine whether The Strategic Coach Program will benefit them on their path. This might sound like a tough task, but it’s deceptively simple.

You see, everyone I talk to already knows how to overcome entrepreneurial obstacles—I simply provide the structure for them to think about their thinking.

At Strategic Coach, we show entrepreneurs how to utilize their past experiences and think in different ways to make their ideal future a reality. We’re not interested in telling entrepreneurs how to act, how to think, or what to do with their businesses—we simply ask great questions that allow them to formulate their own action plan based on their answers. The best way to overcome entrepreneurial challenges is to use the knowledge and experience you already have. Our job is to pull that knowledge out of you and help you put it to good use.

It all starts with a Discovery Call where we go over The R-Factor Question, D.O.S., and what it means to have a Self-Managing Company. Interested? Let me explain …

The R-Factor Question.

When I’m talking to someone who is interested in Strategic Coach or just wants to have more freedom as an entrepreneur, I always start with a question we call “The R-Factor Question,” which was developed by Dan Sullivan.

It goes like this: “If we were having this discussion three years from today, and you were to look back over those three years to today, what has to have happened during that period for you to be happy with your progress?”

Now, what comes next is key: I stop talking and listen. The beauty of this question is that it gives the entrepreneur a chance to think about what they want their life to look like three years from now, and then work backward to understand what needs to happen for them to get there.

Many of the entrepreneurs I speak to are relieved to be able to talk to someone about these things, as it’s not always a topic that can be easily discussed with family members or friends.

The best part about this question and process is that it can work for any entrepreneur in any industry. I don’t have to know what industry someone is in, and I don’t need to have expertise in specific niches. Entrepreneurs know where they want to go in the future—and most entrepreneurs, regardless of industry, face the same obstacles and challenges along the way.

Anyone who is interested in learning how to overcome challenges and obstacles as an entrepreneur needs to first identify the obstacles that are in their way. The R-Factor Question and the three-year vision that comes out of it are the first steps in doing that, which is why we start all of our Discovery Calls with that simple question.

Want to learn more about how Strategic Coach can help you overcome entrepreneurial obstacles? Schedule a FREE 30-minute Discovery Call to get clear on where you’d like to take your business, what might be standing in your way, and whether The Strategic Coach Program is a good fit for you. Book your call today.


Once an entrepreneur understands their three-year vision, everything becomes clear. They can see what they want to achieve and the path that will get them there. But then the obstacles start to appear.

D.O.S. is a simple system that Dan Sullivan created for overcoming entrepreneurial challenges. It stands for Dangers, Opportunities, and Strengths. As mentioned previously, this is not about telling you what to do—it’s about showing you how to utilize the knowledge and experience you already have to overcome entrepreneurial obstacles in your path.

Dangers are just what they sound like. They’re fears you have about life or business, including the obstacles that are standing between you and your three-year vision. Many entrepreneurs fail to actually recognize these dangers and fears, yet it’s absolutely critical to understand and be aware of them.

Opportunities are what come out of those dangers. When you overcome entrepreneurial obstacles, you create opportunities for yourself. Imagine if you could wave a magic wand and the three biggest obstacles in your path disappeared. What opportunities would be available to you?

Most entrepreneurs haven’t thought about this because they’re so focused on the problems. But looking at the future and the opportunities that will come when you solve those problems is the best way to find solutions.

Strengths are what ultimately allow us to overcome entrepreneurial challenges. We all have our own unique capabilities, and we’re never truly starting from scratch. Strengths, past experiences, and capabilities give entrepreneurs the confidence they need to make their three-year vision a reality.

This D.O.S. system might seem simple, but entrepreneurs don’t always get the chance to think these things through. Most are too busy running the day-to-day operations of their business, and they don’t have many entrepreneurially-minded people in their lives to discuss these issues with.

That’s where Strategic Coach comes in. We give entrepreneurs the frameworks and tools to start thinking differently so they can overcome entrepreneurial challenges on their own.

Creating a Self-Managing Company.

We use The R-Factor Question and D.O.S. on our Discovery Calls to show people how to create their three-year vision and overcome entrepreneurial challenges along the way. But what is the end goal of all this?

Everyone’s vision is different, of course, but there is one common thread in nearly every Discovery Call I’ve had. Every entrepreneur I’ve spoken with—regardless of industry, company size, or revenue—wants to create a Self-Managing Company.

A Self-Managing Company is one that runs seamlessly without your involvement in the day-to-day so that you can focus only on what you love to do and do best in your business. It’s the key to the freedom every entrepreneur desires. No matter what your three-year vision is, a Self-Managing Company will give you the time, ability, and freedom to accomplish it.

Our programs can teach you how to overcome entrepreneurial obstacles, but that’s just the beginning. What we’re really doing at Strategic Coach is laying the foundation so that you can gain the capabilities necessary to create your own Self-Managing Company.

The best part? It’s easier than you think. I guarantee it.