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How Are You Defining Your Success as an Entrepreneur?

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Life of an entrepreneur can often be described as an emotional roller coaster. You have a few ups and a lot of downs, especially when you are starting out.  Choosing entrepreneurship as a career is for people who can handle the ups and downs – those people who are resilient.  Entrepreneurship takes a lot of confidence and belief that what you have to offer will be valuable to others.

I have definitely had my share of ups and downs as being a business owner.  As the owner of three separate businesses, you might think that by the third business I would be set up for what to expect and an expert at building businesses. You’d think that I’d know by the third time around that I’d know exactly what to do and create an overnight success with my business. But I didn’t.

Regardless of what was happening in my business and how much success I was experiencing, I found it wasn’t quick enough, or I would hone in on my weaknesses rather than my strengths.  I would focus on the negative and not be grateful for what was going well.  I found myself letting that fear of failure and impatience creep in.  “Why aren’t I hitting my revenue targets?  I’m a failure.  What’s wrong with me?”  These are questions I would beat myself up with and punish myself.

It was like no matter what I did it wasn’t good enough, fast enough, or just enough.  What were my expectations?  What was I trying to meet?

These are all messages that can creep into your mind and play that game with you.  It makes you question your worth, what you are doing, and above all, your sanity.  You end up wondering what you were thinking, if you even have what it takes, and all the other negative thoughts that can start clouding your judgement, and worse, have you question your self-worth.

“Success is liking yourself, liking what you do, and liking how you do it.” – Maya Angelou

When you start feeling like this, here are some questions you can ask yourself:

  1. Did I set reasonable goals?By reasonable, are they attainable within the parameters that you set out? Entrepreneurs tend to be overachievers and put high expectations on themselves, so be sure that you have set out a plan that works your way up to success, whether your goals are measured by revenue goals, client wins, or whatever else you choose.
  2. Are there clues along the way that I am on the right track? Don’t underestimate the value of non-financial wins.  Those are breadcrumbs on the trail to success.  They are the clues that tell you that you are on the right track and serve as valuable feedback.  Listen carefully.
  3. Am I taking care of myself? When you have put too many hours in and are not taking time to enjoy life, slow down and play a bit, you are leading yourself to burn out.  Burn out is difficult to recover from and entrepreneurs who are burning the candle at both ends and not taking enough breaks are susceptible to burn out.  You need to take breaks, go for walks, get a change of scenery, and enjoy life.  It’s in those moments where you recharge, and you return with more creativeness and clearer thought processes.  That increases your efficiency.
  4. Am I really giving it my best? Be honest here, are you giving it your full effort?  Sometimes we think we are, but when you take a step back and assess the overall picture, you can see the areas for improvement.  Maybe you need to be clearer on your messaging, or you could approach something in a different way.  There is always room to tweak and improve upon a process or system.
  5. Nothing worth having comes easy, or so they say.  And with building a business, the overnight success stories are extremely rare.  Behind most of the stories there are the untold stories of being brought to the brink of bankruptcy, stressful and sleepless nights, small wins, huge wins, setbacks, and failures.

Success is rarely a straight path.  We learn and grow from our challenges.  To create an overnight success does not prepare you for the real challenges of entrepreneurism, as the challenges never go away, they just present themselves differently at each stage.

The true measure of success for an entrepreneur is measured by resiliency.  How you react and reposition after a failure is everything in how you set yourself up for success.  

When you are willing to give yourself a break, accept that building a successful business takes time, and that enjoying the process is just as important as the destination, then you will be able to define a more achievable and reasonable measure of success.

Melissa Houston is a Certified Professional Accountant (CPA) and a financial coach, who helps entrepreneurs overcome both their personal and business finance issues and earn more money. With over 20 years of financial management experience, Melissa understands how to improve your bottom line without making another sale.  Melissa works with business owners through coaching programs and signature course offerings. Reach out to Melissa on her LinkedIn account.

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The Entrepreneur’s Reading List That Transforms Ideas Into Empires

These must-read titles and writing insights reveal how entrepreneurs turn bold ideas into empire-level success.

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top entrepreneurship books for business growth
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Entrepreneurship is powered by stories—of accomplishment, failure, and decision moments that define businesses. Books are maps, providing insight from individuals who’ve traversed the road ahead. (more…)

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Entrepreneurs

The Leadership Shift Every Company Needs in 2025

Struggling to keep your team engaged? Here’s how leaders can turn frustrated employees into loyal advocates.

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Bridging the gap between employees and employers
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In workplaces around the world, there’s a growing gap between employers and employees and between superiors and their teams. It’s a common refrain: “People don’t leave companies, they leave bad bosses.”

While there are, of course, cases where management could do better, this isn’t just a “bad boss” problem. The relationship between leaders and employees is complex. Instead of assigning blame, we should explore practical solutions to build stronger, healthier workplaces where everyone thrives.

Why This Gap Exists

Every workplace needs someone to guide, supervise, and provide feedback. That’s essential for productivity and performance. But because there are usually far more employees than managers, dissatisfaction, fair or not, spreads quickly.

What if, instead of focusing on blame, we focused on building trust, empathy, and communication? This is where modern leadership and human-centered management can make a difference.

Tools and Techniques to Bridge the Gap

Here are proven strategies leaders and employees can use to foster stronger relationships and create a workplace where people actually want to stay.

1. Practice Mutual Empathy

Both managers and employees need to recognize they are ultimately on the same team. Leaders have to balance people and performance, and often face intense pressure to hit targets. Employees who understand this reality are more likely to cooperate and problem-solve collaboratively.

2. Maintain Professional Boundaries

Superiors should separate personal issues from professional decision-making. Consistency, fairness, and integrity build trust, and trust is the foundation of a motivated team.

3. Follow the Golden Rule

Treat people how you would like to be treated. This simple principle encourages compassion and respect, two qualities every effective leader must demonstrate.

4. Avoid Micromanagement

Micromanaging stifles creativity and damages morale. Great leaders see themselves as partners, not just bosses, and treat their teams as collaborators working toward a shared goal.

5. Empower Employees to Grow

Empowerment means giving employees responsibility that matches their capacity, and then trusting them to deliver. Encourage them to take calculated risks, learn from mistakes, and problem-solve independently. If something goes wrong, turn it into a learning opportunity, not a reprimand.

6. Communicate in All Directions

Communication shouldn’t just be top-down. Invite feedback, create open channels for suggestions, and genuinely listen to what your people have to say. Healthy upward communication closes gaps before they become conflicts.

7. Overcome Insecurities

Many leaders secretly fear being outshone by younger, more tech-savvy employees. Instead of resisting, embrace the chance to learn from them. Humility earns respect and helps the team innovate faster.

8. Invest in Coaching and Mentorship

True leaders grow other leaders. Provide mentorship, career guidance, and stretch opportunities so employees can develop new skills. Leadership is learned through experience, but guided experience is even more powerful.

9. Eliminate Favoritism

Avoid cliques and office politics. Decisions should be based on facts and fairness, not gossip. Objective, transparent decision-making builds credibility.

10. Recognize Efforts Promptly

Recognition often matters more than rewards. Publicly appreciate employees’ contributions and do so consistently and fairly. A timely “thank you” can be more motivating than a quarterly bonus.

11. Conduct Thoughtful Exit Interviews

When employees leave, treat it as an opportunity to learn. Keep interviews confidential and use the insights to improve management practices and culture.

12. Provide Leadership Development

Train managers to lead, not just supervise. Leadership development programs help shift mindsets from “command and control” to “coach and empower.” This transformation has a direct impact on morale and retention.

13. Adopt Soft Leadership Principles

Today’s workforce, largely millennials and Gen Z, value collaboration over hierarchy. Soft leadership focuses on partnership, mutual respect, and shared purpose, rather than rigid top-down control.

The Bigger Picture: HR’s Role

Mercer’s global research highlights five key priorities for organizations:

  • Build diverse talent pipelines

  • Embrace flexible work models

  • Design compelling career paths

  • Simplify HR processes

  • Redefine the value HR brings

The challenge? Employers and employees often view these priorities differently. Bridging that perception gap is just as important as bridging the relational gap between leaders and staff.

Treat Employees Like Associates, Not Just Staff

When you treat employees like partners, they bring their best selves to work. HR leaders must develop strategies to keep talent engaged, empowered, and prepared for the future.

Organizational success starts with people, always. Build the relationship with your team first, and the results will follow.

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Entrepreneurs

What Makes an Entrepreneurial Leader? Traits of the World’s Best Innovators

Inside the mindset of entrepreneurial leaders who transform risk, passion, and vision into world-changing results.

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When you think of Richard Branson (Virgin Group), Bill Gates (Microsoft), Steve Jobs (Apple), Rupert Murdoch (News Corporation), and Ted Turner (CNN), one thing becomes clear: they are not just entrepreneurs, they are entrepreneurial leaders. (more…)

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Entrepreneurs

Building a Business Empire: Lessons from the World’s Boldest Entrepreneurs

Learn essential lessons, success strategies, and mindset shifts every aspiring entrepreneur needs to overcome challenges and build a thriving business.

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how to build a business empire
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Back in July 2017, I attended a business seminar on entrepreneurship in India. With my appetite for learning and meeting new people, I wanted to explore the latest developments in the entrepreneurial world. (more…)

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