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Top 7 Business Regrets (And How To Speed Up Success)

IN THIS ARTICLE: On the path to success, it’s easy to stumble and make mistakes — and even do things that you later regret. In this article, you’ll read about 7 of the business regrets we have as we grew our business so you can avoid them and grow that much faster.

What are the top regrets of business owners? How can aspiring business owners and startup founders leverage the do-over list of more experienced business leaders and entrepreneurs, gain the edge, and get on the fast track success, without enduring the sticking points of those that have been there before?

Tap into these insights from the successful, leap over the hurdles that slowed them down, or bankrupted their first attempts at launching a venture, and hack your way to more of the results you crave…

1. Not Knowing the Right Questions to Ask

Starting a business, investing profitably, growing income and wealth, getting to your goals; it’s all about problem solving. Albert Einstein said “If I had an hour to save the world, I would spend 55 minutes defining the problem and only 5 minutes finding the solution.”

Harvard Business Review, and Fast Company columnist Warren Berger highlights the importance of asking the right questions as using ‘The Power of Inquiry to Spark Breakthrough Ideas”, and reminds us how deeply integrated question asking is in the DNA of companies like Airbnb and Google.

Michael Hyatt who runs one of iTunes’ top business podcasts, is a New York Times Bestselling Author, and former CEO of a top 10 publishing company says the more successful people are, the better they are at asking the right questions.

Asking good questions is productive, positive, creative, and can get us what we want. So how do we ask more of the right questions?

Ten quick tips for asking good questions:

  1. Go back to your core goals and ask how to make those happen
  2. List the things that you don’t know
  3. Get outside input
  4. Ask open ended questions
  5. Throw out all assumptions
  6. Get multiple opinions
  7. Ask follow up questions
  8. Listen, and let others fill the silence
  9. Ask probing questions of others to get to the heart
  10. Recognize the separation of speculation and fact

2. “Getting Comfortable with Being Uncomfortable”

Life Hacker credits the above quote to the U.S. Navy SEALs. During training, SEALs and other elite military units push themselves to the brink. They do it on a regular basis. Once you’ve faced your worst fear voluntarily, there is nothing to be afraid of anymore.In fact; you can now rush head first into the mission courageously and confidently. And it builds immunity.

Fortunately, suggests that the best way to build this immunity and momentum is via small efforts. You don’t have to strike out with battling hyperthermia or trying to survive alone in the wilderness. You can start with skipping breakfast, or trying a new coffee shop, or sending someone new an email. Whether you aren’t used to asking questions, paying attention to the math, selling, or making big financial decisions; business can be uncomfortable. That just means that you are forging your way into new territory – success territory. So get comfortable, and make peace with the fact that you just need to learn to enjoy the experience.

On the bright side Psychology Today says that you can treat yourself during the process to increase your comfort level in a new way with every step.

5 ways you can minimize the discomfort and create a habit of embracing being uncomfortable:

  1.  Get out for a run, or walk
  2. Journal
  3. Focus on the discomfort of others, not your own
  4. Meditate and find your focus each day
  5. Treat yourself to a massage or shopping

3. Thinking about Yourself, Versus Adding Value to Others

You can have everything you want in life if you just help enough people get what they want in life.” – Zig Ziglar

It’s natural to think about ourselves. After all, that is the driving factor that inspires people to go into business, or even motivates them to get out of bed and apply for a job. But at some point, CEOs and businesses find that internal focus, and a taking mindset sabotages them. It can wreck the biggest and best funded organizations fast. And often there is no coming back from that.

The reality is the more people you serve, the more success you will see. The more customers you help, the greater the revenues. But this giving mindset must be authentic, and must be built into the DNA of the business from the beginning.

4. Not Understanding Leverage

Leverage is the most powerful tool available to entrepreneurs, investors, and businesses. Yet, it is frequently misunderstood. It can make all the difference in success. Or it can doom an individual and enterprise to bankruptcy.

The entire US and global economy, and real estate markets are all built on leverage. And we’ve seen how leverage can help them grow, and destroy them. The key is to appreciate the benefits of leverage, while never forgetting to fear the outcome of over-leveraging. Call the optimal mindset a healthy respect for leverage.

Used well it will help you get more done, faster. It may even be the pivot that ensures success. And there is more than one type of leverage. There is financial leverage, intellectual leverage, labor leverage, and leveraging business assets.

5. Creating a Team Too Late

Warren Buffett, Richard Branson, Facebook, Google, Airbnb, or Uber – all of them leverage people. None would be where they are without great teams. So it only makes sense that the earlier you create a team, the better it is. The trap that many entrepreneurs fall into is trying to start alone, and then never finding that ‘perfect’ moment to build the team, and actually allow themselves to step back, and move up.

Start as you mean to finish. Thanks to new outsourcing platforms like Upwork, even solo entrepreneurs can begin building a team on-demand immediately, without burdening themselves with overhead.

6. Trying To Do It All By Yourself

A cord of three strands is not quickly torn apart.” – King Solomon

King Solomon is regarded as one of the wisest and wealthiest of all time. Worth an estimated $20 billion, the author-king wrote this advice around 3,000 years ago . Today, venture capital firms prefer funding businesses with multiple founders. The largest and richest businesses have shareholders. These are all forms of partnering up. Those seeking likeminded business partners can check out tools like CoFoundersLab.

Even those that want to go it alone can find many way to leverage others through outside strategic partnerships. Look for vendors, other small local businesses, or others in your industry that can complement your work, without competing, and find mutually beneficial ways to work together.

7. Listening to Advice from the Wrong People

Don’t take advice from someone whom you are not willing to trade places with.

Getting advice on both what to do, or not to do is critical. But it only helps and has value if it is from the right people and sources. Gaining good advice is all about modeling success. The opposite of that is taking input from the unsuccessful, and plugging that into your business. That’s like a deadly virus. Sometimes you think it is good medicine at first, it’s only when the bad symptoms start showing that you know it isn’t the good stuff. Sometimes by that point the infection and damage is just too bad to repair or cure.

This is what is so dangerous about all of the cheap and free information available today. Free online investment forums are often riddled with thousands of newbies, all trying to coach each other. Some have no idea. Others are openly committing fraud. If you are new, you might not have any clue. So look for sources of success, and do your due diligence on them before putting any advice into your operation.


Avoid these business regrets, and hack your way to the top faster. Don’t just duck or dodge them, add the opposite activities to your to-do list. List your questions, practice getting uncomfortable, look for ways to add value and serve others, gain a healthy respect for leverage, start hiring a team, schedule interviews with potential partners, and find great mentors that will help you model success.

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