How to Stay a Successful Entrepreneur: Setting Yourself Up for Lasting Success

Dr. Young sits on his couch and reads, demonstrating an open-mindedness to learning and growth that's required to remain a successful entrepreneur.

by Dr. D Ivan Young, ICF Master Certified Coach

Maintaining your status as a successful entrepreneur is a much greater challenge than attaining success. Many achieve their goals only to lose everything because they lack the skills to maintain them. 

As an entrepreneur, you’re either in the midst of a storm, coming out of one, or about to enter one. 

The Transtheoretical model of change involves six stages. The first two stages are pre-contemplation and contemplation. Then comes preparation and action. Finally, there’s maintenance and termination. 

If you’re reading this now, you’ve contemplated plenty. You’ve prepared and taken action. Now, you’re in the maintenance stage. You’re trying to figure out how to keep the success you’ve earned. 

Many of my entrepreneur clients are in this stage when they come to me for coaching. Together, we figure out what’s holding them back, what they need to do to maintain and increase their success, and what they want their lives to look like overall. 

If you want to remain a successful entrepreneur, there are certain steps you can’t afford to skip. There are also pitfalls you must avoid. 

What to Avoid If You Want to Maintain Success as an Entrepreneur

Most of us think that if we make a certain amount of money or attain a level of notoriety or power, then we’ll be happy, and life will be perfect. Thinking this way will get you stuck in a revolving door of unfulfillment and frustration. Furthermore, this attitude can get you into trouble and lead to poor outcomes. 

If you set yourself up to believe you’ve made it, that’s the first step toward failure.

If you want to remain a successful entrepreneur, you have to avoid this mindset that neglects learning and growth. 

There are many psychological and environmental factors that contribute to one’s success as an entrepreneur. Different types of support, such as moral, financial, and social support, play a key role, but they aren’t the sole determinants¹

You can still become and remain a successful entrepreneur when the odds are against you. As an African American man who was adopted, I felt like I lacked emotional and social support, even though I didn’t grow up in poverty. Because I was always adjusting the way I spoke and behaved, I struggled with socializing and connecting with people. I really had to work on understanding myself and being able to bounce back from tough times. As I pursued my dream of becoming a successful entrepreneur, I found myself constantly thinking about the lessons I learned from both my failures and my achievements. 

Qualities of Successful Entrepreneurs

My most recent article discusses the importance of focusing on what you can do for your clients and how your purpose helps others. Honing in on your “why” is one of the most effective strategies that can help you remain a successful entrepreneur². It helps with staying motivated, communicating properly, and making a difference

Other qualities that almost every successful entrepreneur possesses include:

  1. Discipline – motivation comes and goes, so you must hold yourself accountable.
  2. Resilience – you must be willing to fail, learn from your mistakes, and move forward.
  3. Self-awareness – you should be aware of your strengths and weaknesses and be willing to delegate when necessary.
  4. Open-mindedness – if you aren’t willing to change your approach, adjust your mindset, or confront your limiting beliefs, you won’t make it far. 

Some publications suggest that entrepreneurs should also have business skills, be risk takers, and be decisive³. However, these characteristics are developed through trial and error. Don’t assume you don’t have what it takes if these qualities aren’t second nature to you yet

Nobody is born to be an entrepreneur. You can develop these successful entrepreneurial qualities if you’re willing to learn as you go. 

If you’re reading this right now, you’re likely ready and willing to learn what it takes to maintain your status as a successful entrepreneur. So, what’s next?

How to Be a Successful Entrepreneur and Stay One

We’ve covered what it takes to be a successful entrepreneur. Now, there’s only one thing left for you to do: keep taking the right actions. 

You’ve made it this far. You know you have what it takes to succeed, but you must keep working at it to sustain your success. Odds are, you’ve gotten where you are by developing the qualities we discussed. So, how do you maintain these qualities and improve upon your weaknesses?

1. Reflect on what worked and what didn’t.

You can’t become a successful entrepreneur by pretending your mistakes didn’t happen. And while it’s important to celebrate what went right, you also have to take some time to figure out why it went right. 

There’s a lot you can learn from your wins and losses

2. Double down on what worked. 

Early on in my practice, I set benchmarks. I’ve met every benchmark and learned that new levels come with new devils. 

I remember saying I’d be happy with a certain amount of money. Now that I’m much wiser, reality has taught me that I must change how I measure success. When I adjusted the way I viewed and approached success, I ended up hitting those other external goals. 

My main takeaway from being a successful entrepreneur in the coaching industry is that true success is measured by how much of a difference I’ve made in the lives of others. This includes my clients, loved ones, mentors, and anyone else who comes into my life. 

3. Regularly revisit your beliefs and habits. 

Stop defining yourself using outdated belief systems and measurements. Reexamine your core values, identify which beliefs hurt or help you, and adjust your goals if necessary.

You can’t accomplish new goals if you aren’t willing to shed beliefs and habits that no longer serve you

How I Became a Successful Entrepreneur and Maintained My Success

I had a failed business, but now I have a successful business. 

What changed?

I did. And let me tell you, all that change was no picnic. It took getting clear on my goals for myself and my clients and taking intentional action day in and day out. I’m always working on myself and evolving my coaching strategies. 

Even after I became an ICF Master Certified Coach and National Board Certified Health and Wellness Coach, I still had to work at it. You have to be willing to grow and adapt to remain a successful entrepreneur. Otherwise, you’ll be left behind. 

So, keep figuring out what your clients want and need, continue developing your skills, learn from every experience, and use this time to become who you’re meant to be. This is your season. 

If you need some support and guidance along the way, follow me on LinkedIn and sign up for my email list. 

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Bio – Dr. D Ivan Young is an expert on human behavior and relationships. He’s a Master Credentialed expert on personality type, an ICF credentialed Master Certified Coach, a Certified Professional Diversity Coach, and a National Board Certified Health and Wellness Coach. Dr. Young is also a member of the prestigious Forbes Coaches Council.   

  1. https://core.ac.uk/download/pdf/234624389.pdf 
  2. https://www.diva-portal.org/smash/get/diva2:1546547/FULLTEXT01.pdf 
  3. https://hal.science/hal-01484491/document