3 factors to consider before leaving your startup

The opinions expressed by entrepreneurs contributors are their own.

When I was approached by to buy my business when I was in my twenties, I jumped at the chance. Well, who wouldn't?

To give some background: a college friend and I had become interested in certain facets of cybersecurity and decided to develop anti-spam software, quickly followed by anti-software. This was before machine learning technology existed, but it was already a buzzword. We successfully launched GIANT Software and our business quickly grew exponentially.

Just one year after the launch of our flagship product, Microsoft contacted us. They loved what our technology offered and in no time GIANT became Microsoft Anti-Spyware, and my co-founder and I were hired into the company.

Decades later, and having had time to reflect on past choices, there are a few key things I would encourage others in a similar position to consider before making a decision.

Related: Start planning your exit strategy now with these 4 tips

The grass isn't always greener

Everyone has a 20-20 view in hindsight. Looking back, there is an argument to be made that I should have waited longer and not sold my business so soon - however, not necessarily for the reasons you might think!

The period immediately following the acquisition was exhilarating. We moved to new offices in a new part of the country, hired hundreds of new people for my team, and used resources we never had before. It was really exciting, and I felt like I was still able to tackle some big issues head-on.

However, eventually boredom set in. We went from startup mode to enterprise mode so quickly. New internal processes, systems, and policies that didn't exist or weren't relevant before suddenly became an important part of my day.

If you are an entrepreneur and your business is taken over, you may become inactive. The day-to-day wasn't as exciting as it had been, and I missed the creative buzz, the rush, the "reach for the stars" impulse that you have when you're in the building phase.

> Have a backup plan

That's why my next piece of advice is: always have a backup plan after you leave. Think about where you want to go next, whether in the same area or coming from a completely different direction. It's always a good plan to have the next ideas up your sleeve.

For example, following my GIANT project, I chose to focus on different areas of technology, including e-commerce, graph theory and consulting. Trying out a number of things and learning through hands-on experience can offer all kinds of inspiration, as well as help you grow your network and make connections.

Finding a colleague or partner who is on the same page as you can also be more interesting at the same time. Two heads are better than one, and collaborating on projects will broaden your horizons. And of course co-workers who relax at the end of the day in the same way certainly contribute to work-life balance: a little part of Call of Duty anyone?

Related: How to Create Your Ideal Business Exit

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