• Su Guillory

Are You Ready to Start a Second Business? Here Are 5 Signs You Should Take the Plunge

This was originally published on AllBusiness.


For a lot of people, starting one business is the pinnacle of success. They put all their energy into launching, growing, and stabilizing that business, and assume they’ll run it until they retire.

Then there is that smaller faction of people who aren’t satisfied with birthing just one business. They may create a second, a third, or even a dozen businesses over their professional lives.


So which are you? Even if you never considered starting a second business, here are the signs that it might be time to try something new.



Should You Start a Second Business?


1. Your business is pretty much on autopilot

The hard work of getting your business off the ground and struggling to make ends meet is years in the rearview mirror. Now, things are easier. You’ve hired smart people who make sure things are running smoothly, and perhaps you don’t need to be involved in every aspect of the business anymore.


You could enjoy your free time—or you could consider your next business venture.


2. You’re being pulled in a particular direction

Jen has a successful business helping companies sell products on Amazon and in Walmart. Her business is thriving and she’s pulled away from needing to be the key person with clients. In her spare time, she finds herself having conversations with people about dating and relationships. Like, a LOT of conversations.


I worked with Jen as her business coach, and together, we realized she was being pulled in the direction of dating and relationships for a reason: her heart sings when she helps people navigate what can be a tricky landscape. Now, she continues to run her established business—and she’s launched her dating and relationship coaching services as well!


If your intuition keeps nudging you in a certain direction, pay attention. If it’s something you’re genuinely excited about, consider whether that could be simply a hobby, or if it has potential for a new business idea.


3. You’re no longer challenged in your business

Many of us have been there: we put our hearts into our businesses, sometimes for decades, and then we simply lose passion for it. That’s not to say you need to shut down your existing business (especially if it’s a solid source of income), but I’m a firm believer in combining passion and business. If you aren’t feeling that excitement about what you’re doing, consider what you might enjoy more.


Maybe that’s getting certified in Reiki to provide healing to animals. Teaching art to kiddos. Becoming a massage therapist.


There are no rules about what you’re “supposed” to do as an entrepreneur. You can run one business or four at the same time, as long as you have the time, energy, and love for what you do.


4. You’re ready to birth something new

Remember that feeling when you first started your business? It was equally terrifying and exhilarating, wasn’t it? If you’re like me, you had no clue what you were doing, but somehow figured it out.


If you have the energy to do it all again, know that this time around it will be easier. You have years of experience you didn’t have then, and maybe more of a budget to hire people rather than doing it all yourself (I cringe at the logo I designed for myself back in 2006!). You already know what it takes to start a business, so you can apply that wisdom to something entirely different from what you do now.


5. You can take your time to get there

As you well know, there’s no such thing as an overnight success when it comes to starting a business. The best time to start another business is when your first one is doing well, not when it’s struggling. You need to be able to rely on that revenue while you build a new client base with the new company.


As the new business starts to see profits, you can either continue to run your existing business or slowly pull back from it. It’s helpful to create a timeline for what that transition might look like so you don’t end up working 80+ hours a week between the two companies.


When NOT to Start a New Business

As I said, you don’t want to start a business when the first one is struggling. Nor do you want to start one to run away from what you’ve been doing.


Years ago, I dreamed up creating a center for entrepreneurs. I made big plans—until I realized that what I really wanted was to not keep offering public relations services. Rather than borrow hundreds of thousands of dollars to start a new business I wasn’t all that excited about, I made the simple decision to shift my business focus away from PR and toward content.


It’s important to move toward a new business for the right reasons, rather than running away from something you don’t like.


I also don’t recommend starting a new business when your life is in upheaval. Whether that’s having a baby, moving, losing a parent, or any other major life event, adding to that stress isn’t going to lay the foundation for a successful business. Wait until the right time. You’ll know when it is.


Feel the Rush of Starting a Second Business

For many entrepreneurs, starting a second (or third) business reinvigorates them. It provides the opportunity to make strategic decisions, reach new customers, and do something completely different and exciting.

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