Connect with us

Success Advice

The One Question to Ask if You Are Struggling with a Decision

Published

on

Image Credit: Unsplash

If you’d like to learn how to make strategic decisions so you can be successful, sign up for the free 90-Day Master Class hosted by the founder of Addicted2Success.com, Joel Brown.


A number of years ago, I was struggling with a big decision. I was a full time instructor at a local college. I was in charge of their multimedia program – training students on fun things like video editing and web design and graphic design. 

Students came to class motivated. They enjoyed it as much as I did! It was a great setting! Yet, I noticed the longer I was there, the more extracurricular activities I was expected to take part in – review other academic programs, fill out a great amount of paperwork about interviews and classes and proposed courses, be a part of improvement-process teams, etc. 

It began to feel like the ‘other stuff’ was keeping me away from what I enjoyed most – being in the classroom and helping the students. Then there was this other unique opportunity that was growing. Since I was the main contact within the community for knowing web design and graphic design, the local businesses started calling me. 

They wondered about getting a website, a logo, a flyer, or a video. Some of the projects were ideal projects for students, and the local business was ok with that. Other projects were either beyond the scope of a student project or the business wanted me to do it. Since I had always had an entrepreneurial spirit, I began to wonder if these opportunities were more than just a side hustle.

After a few years of balancing out the full time instructor position with the ‘side’ projects, I realized I had a decision to make.

The Options

I could continue as is – although one of my ‘jobs’ would ‘suffer’ and it would likely be the ‘side hustle.’ I tend to be loyal to my commitments and I wasn’t willing for my full-time job to suffer if I was taking projects on the side. 

If I chose the full time instructor option, the projects on the side would suffer. Not suffer in quality, but suffer in quantity. Maybe it was more that I would ‘suffer’ because I wouldn’t be able to do as many of them as I would like.

Or, I could just choose one of the options. I could forget the side hustle and focus on being an instructor at the college, along with the other commitments that were expected of me. Although, even with this option, I knew I would continue doing at least 1-2 side projects. It was part of my philosophy of being an instructor. I needed to stay in touch with the real world to be of most benefit for my students. 

The other option would be to walk away from the instructor position, even though I knew I’d miss the student interaction. Instead, I’d go full time into doing my own business.

Both of these had similar pros and cons list. One’s pro list was the other con’s list and vice versa.  It wasn’t that one was necessarily better than the other, although there was one that was probably right for me.

As I struggled with the decision, there was one question that kept coming up, and it was the answer to this question that showed me the right decision for me.

“What would you do if you weren’t afraid?” – Sheryl Sandberg

The One Question

The question to ask: Will you regret not taking this opportunity if you were to look back at this moment in 5, 10, or 20 years from now?

Back to my situation of choosing between staying a full-time instructor or doing my own business full time. I knew I would not regret not staying a full-time instructor. I could always find a similar position elsewhere. But, I did know that I would regret not taking this opportunity to go full time into my own business. Yes, I could go full time into my business at any time, but the stars seemed to be aligned at that moment.

I could not not take the opportunity to grow my own business. I knew that in the future I would regret not taking advantage of the opportunity that was kind of being handed to me.

I knew my next step. The answer to the question, ‘Would you regret…?’ told me the right decision for me.

It’s Not Without Risks

Yes, it meant missing the classroom – although I had ideas on how I could do that within my business and not have to get involved in the politics of being an instructor at a college. By the way, that happened to work out just like I had hoped!

Yes, it meant taking a bigger risk of not having a regular paycheck, not having benefits, having a lot more unknowns – but doing something I’ve always dreamed of doing – having my own business.

Knowing what I would regret if I was to look back at this moment in the future, helped me make the decision I needed to make at that time. And, in hindsight, nearly 20 years later, I’m so glad I did!

“Don’t be too timid and squeamish about your actions. All life is an experiment. The more experiments you make the better.” – Ralph Waldo Emerson

Would you regret …?

What is the decision you are facing? More importantly, what is it you would regret in the future if you were not to make this move, or take this job, or …?

What would you regret not doing, if you were to look back 10 or 20 years from now, or maybe even 1 year or 5 years from now?

The one thing you hear most from people nearing the end of their life on earth are the words ‘I regret.’ 

Let that stark reality be the motivator and inspiration when it comes to making decisions about your life. Next time you are faced with a decision and are not sure what to do, ask yourself, “Would I regret not doing ….?” If the answer is yes, you know the right decision for you.

What strategic ways do you use to make a decision you’re struggling with? Share it with us below!

Carma Baughman is a tech trainer and people developer. She has enjoyed the solopreneur lifestyle for nearly 20 years. She supports others in pursuing their dreams and living life by their own unique design, helping them discover their contribution to the world.  Learn more at carmabaughman.com.

Advertisement
Click to comment

Leave a Reply

Your email address will not be published. Required fields are marked *

Success Advice

Why One-Size-Fits-All Leadership Will Always Fail (and What Works Instead)

The surprising truth about leadership styles that can make or break your team’s success.

Published

on

Why one-size-fits-all leadership doesn’t work
Image Credit: Midjourney

Leadership has always been as much about people as it is about performance. Ken Blanchard, in his influential book, “The One Minute Manager”, put it simply: different strokes for different folks. (more…)

Continue Reading

Success Advice

What Every New CEO Must Do in Their First 100 Days (or Risk Failure)

Your first 100 days as CEO could define your entire legacy, here’s how to make every move count

Published

on

leadership tips for new CEO
Image Credit: Midjourney

When Tim Cook took over from Steve Jobs at Apple, the world watched with bated breath. Jobs wasn’t just a CEO; he was a visionary, an icon, and a legend of innovative leadership. (more…)

Continue Reading

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.

Published

on

Bridging the gap between employees and employers
Image Credit: Midjourney

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.

Continue Reading

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.

Published

on

entrepreneurial leadership skills and traits
Image Credit: Midjourney

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…)

Continue Reading

Trending