While I consider myself a lifelong Ideapreneur, my true entrepreneurial adventures began about ten years ago, right around the time I became a mom. Along with my first foray into freelance writing, I started an online retail business selling organic baby items like mattresses and glass baby bottles. This isn’t so cutting edge today, but back then I was on the right side of something big. Within a year I had turned that business into a well-oiled machine, with higher than industry-standard profit margins and low overhead.

The Inevitable Entrepreneur’s Dilemma

I kept at that pace for another year and a half, focusing on one product line in particular because it made good business sense. But my kids were getting older, I was overwhelmed, and frankly, I found myself becoming a little bored with the same thing day in and out.

I wanted to grow — to expand. I wanted to open a brick and mortar and carry new stock. I had grand visions for the business. At the same time, there was something about spending tens of thousands of dollars and changing my whole life to accommodate these changes that didn’t make sense when things were already going so well.

So, instead of investing into the business, I sold it, and when I got down to the root of this decision, there were two main factors:

1.) My personal life was suffering because I couldn’t keep up with the house and my kids were quickly growing, demanding all of my attention.

2.) The business was suffering because I was falling behind on paperwork, and I dreaded dealing with day-to-day tasks.

To Invest or Not to Invest?

The bottom line is that had I kept the business I would have needed to make some investments. I would have needed to invest in my personal life by hiring a housekeeper and finding child care. I also would have needed to invest in my business by hiring an accountant, purchasing inventory and, most likely, hiring a staff member.

These are the two sides of entrepreneurial growth: all decisions must take into account our personal lives and professional lives. Our business moves impact our personal lives in a very tangible way. As entrepreneurs we don’t have a guaranteed income, and usually, there are limited resources, so there is imminent risk if things don’t go well.

I’ve never regretted the decision to sell my business because I felt like it was time to move on, but it wasn’t an easy choice. There were tough questions I had to ask myself, and I’ve had to ask myself them again over the years as new projects have popped up and goals have shifted.

How to Solve the Dilemma

Today I wanted to share some of the questions that have helped me decide whether or not it was time to invest in myself/my business.

1. Are things too stagnant?

If something fired you up, and was going well, but has leveled out and feels stagnant, it might be time to invest in growth somehow. That might mean a business coach or expansion of retail space, or even offering new products. Sometimes all it takes is a little shift to make us remember why we loved something.

2. Is this a step toward my dream?

If you’re chasing your dream, I mean REALLY chasing your dream, then you’re probably going to have to invest: a Master’s degree, a bulk order, an AirBnB cottage in the woods to finish your manuscript. Before you dive in deeper, ask yourself if your next step is taking you closer to your dreams and goals, or if it’s just passing the time.

3. Am I in over my head?

It can be hard to admit that we’re in over our heads, but it’s important that we do acknowledge this so that we can get help! It can be difficult for us to ask for help, but if you’re feeling overwhelmed, consider it might be time to reach out and delegate. Pick the one thing that you can imagine handing off, and send it away.

4. What’s that voice saying?

I recently hired a developmental editor to help me rework a novel I’ve written, and let me tell you: it was a long time coming. I knew it needed to happen. I knew I needed it for so many reasons, but something held me back. Once I sat back and realized that investing in this editor was a very important stepping stone toward my dream, it took that pressure off me, and I knew it was the right thing. That voice is there for a reason, be sure to hear what it’s saying!

What is your experience with investing in yourself as an entrepreneur?
Do you have anything to add?