How To Make Difficult Decisions At The Crossroads Of Business: 3 Lessons Learned On The Entrepreneurial Adventure
Feb 02, 2026
Have you ever arrived at a crossroads in your business and been faced with an important choice about how to continue?
It’s the kind of choice that has the potential to set the trajectory of your business on a completely different course. So no pressure, right?
“We are getting real about the moments that shape our businesses—the ones that feel like crossroads.” Kim White
There are two extremes when it comes to making decisions at the crossroads of business.
You can keep doing something because you’ve always done it. But, that’s not a good reason. Or you can quit because it didn’t work out the way you wanted it to. But, that’s not a good reason either.
Here are 3 lessons learned about how to navigate the crossroads with wisdom from decades of experience on the entrepreneurial adventure.
1. Show Caution And Consideration
Would you speed through a traffic intersection? Of course not. It could have terrible consequences for you, everyone involved on the scene, and more.
Crossroads in business are no different.
Lesson #1 is to slow down and show caution when approaching a crossroads. And while you’re slowing down, consider your people.
“Sometimes when you try to go too fast with something, you start discombobulating your clients, your customers, your followers, your audience. It can be very abrupt” Kim White
Feeling change is hard, even when it's good.
“Sometimes we need to change things gently.” Jill Olish
Remember that any decision you make is going to have an impact on the people you work with and work for.
Going slow, and considering the impact on your people will help you navigate the crossroads wisely to make the best decision for your business.
2. Making A Choice VS Making An Investment
“Think about every chance, possibility, or opportunity as something you’re choosing. Are you going to invest in it or not?” Kim White
Lesson #2 is this: when you’re at a crossroads in your business, your decisions need to be about your investments.
Not the stock market kind of investments. But where to invest your time, your energy, and your heart.
When you are investing your time, energy, money, heart, and bandwidth in the right places, you’re doing business in a smart way, where you still have a life.
At the crossroads of business, ask yourself, "What do you need to put your effort into? Where do you need to be investing?"
“If something isn’t working, do you need to invest in making it work and doing it better? Or do you need to pull out altogether and invest somewhere else?” Jill Olish
Considering your investments is how you navigate the crossroads wisely and decide which direction to take your business, team, clients, or audience.
3. Take The Human Out
Sometimes, the platforms you use in your business can force the crossroads into your path.
“You can love something - a product, brand, or platform, and then they shift.” Jill Olish
When you are an entrepreneur in the virtual space and a platform you rely on makes some big changes, it can be a major disruptor for your business. And there’s often nothing you can do about it except shift your whole business with them or start fresh somewhere else.
It’s easy to get caught up in the frustrations of having this dilemma forced on you and your business, and then let those emotions drive your decision-making process.
Here is lesson #3. You might need to take your human out of the process for a bit, so you can slow down and then start considering your people who will be impacted by this decision.
How can you shift (with or without the platform) that will be the least abrupt and painful for them?
Then you can decide how to invest your time, energy, and bandwidth regarding that particular platform.
But whatever you do, follow through. Be there for the people you said you were there for. Don't underestimate what follow-through does for your business.
“I think our businesses are worth following through for. If you're on a platform and you're not following through, I think it's a consideration of whether you should be on the platform or not.” Kim White
Crossroads don’t always come with flashing lights or easy answers. You do need to be cautious of the shiny new things and confident to honor what’s already working in your business.
Don’t give up on something that actually works. And don’t choose to keep doing something that is absolutely not working.
“We're doing our best to get encouragement and inspiration out there because we know we've needed it.” Kim White
We work on this exact process together in our signature “Not Creepy Room” on the Clubhouse Audio app, where you can get real-time feedback, practice your pitch, offer or intro, and connect with fellow entrepreneurs. Come hang out with us on Wednesdays 8-9am CST in the My Sexy Business House.
Our Groundwork Brigade is a home for entrepreneurs who want to build a business that they own and that doesn't own them. It’s a community of like-minded entrepreneurs finding freedom in the entrepreneurial adventure by practicing putting the right things in the right order.
It’s a safe space to learn how to build a relational business using irresistible marketing strategies, tailored to your individual needs, in a group setting, with lots of accountability and support.
If you missed the conversation between Kim and Jill on their podcast Buckets and Boom Gates, you can catch it here.
To connect and find out more about Kim or how to create a sexy business for a sexy life, you can reach her and the My Sexy Business Team at www.mysexybusiness.com.
And to connect with Jill Olish go straight to her website www.mamaoutspoken.com and you’ll find her there!
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