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



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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

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