The Boldest Moves I Made Before Age 40

This month, I’m celebrating my 40th birthday – a milestone that has me reflecting on my life journey in many ways! In honor of this moment, I wanted to look back at some of the bold moves I’ve made over the years, why they mattered, and how they’ve shaped both my life and my business.

Being bold doesn’t mean being fearless. I’m actually pretty calculated when it comes to risk-taking. But the truth is, no one is going to swoop in and rescue us from situations that aren’t working. Sometimes, we must find the courage to make big changes, even when the outcome is uncertain.

What I’m going to share is a mix of personal and professional decisions – not to put myself on a pedestal, but in the hope that it inspires you to take the bold steps that you know you need to take, deep down. Because the right move at the right time, no matter how hard it feels in the moment, can open doors you never knew were there.

Bold Move #1: Changing direction regarding my college education a few days prior to moving into my dorm

After high school, I got my first job as an office assistant at a machine shop. I really liked the work I was doing, and the small office setting gave me opportunities to problem-solve and try new things.

I was set to leave my job at the end of summer and move into a dorm at a university away from home, but I wasn't feeling as excited as many of my friends were. My mom must have gotten the same vibe, because when we were packing, we talked about how frustrated we were by some of the disorganization we were experiencing from the university. 

She said something like, “Maybe we should just switch to somewhere else.” I immediately agreed – and we withdrew my enrollment that afternoon.

Instead, I enrolled in a business program at a local technical college, which had a credit transfer agreement with another university in our state. I really enjoyed my classes, and the best part was that I was able to keep my office assistant job while attending college during the evenings.

Lesson Learned: Sometimes the “right” path isn’t the one you planned months – or even years – in advance. Staying open to change, even at the last minute, can lead to an outcome that fits you far better than the original plan.

Bold Move #2: Leaving my corporate job with benefits at age 26 without having a job lined up

I had a corporate career for many years while attending and after finishing college, and surviving many rounds of layoffs during 2008 and the recession that followed. But that left me in a role that wasn't suited for me. I had no idea what the next stage of my career looked like. All I knew was that I needed to make a change. I desired more control over my time, the work I did, and who I worked with.

So, I saved up a little money, gave my notice, and three weeks later found myself unemployed.

To find my footing, I attended a networking luncheon and landed a consulting gig. This work led me to learning about Virtual Assistants, and I decided to launch my business. My business took off, largely because I established an office at a coworking space that was full of solopreneurs who needed business support. And the rest is history! 

Lesson Learned: You don’t need to have the entire staircase mapped out to take the first step. Trusting yourself, even when the next chapter is unclear, creates space for unexpected opportunities to find you.

Bold Move #3: Choosing to go from solopreneur to CEO

My business was growing, but I was the only one doing “all the things.” My DIY mindset was deeply ingrained since my childhood, so the idea of building a team was a hard sell… in the beginning.

Hiring my first team members felt like a huge risk, to both my reputation and income. Would I lose any clients? What if the work was done poorly? What if I couldn't pay my team or bills?

But as soon as I started building a team and scaling with intention, this has had a positive domino effect on the rest of my business. I continued hiring team members, closing larger contracts, and investing in software, tools, coaching, and more. Today, we have a thriving team and I’m a true CEO. 

Lesson Learned: Growth often requires letting go of control and trusting others to share the work. When you invest in people and systems, you create capacity for bigger opportunities and a stronger business.

Bold Move #4: Choosing Alignment Over Comfort 

In both my personal life and in business, there have been times when I realized that certain relationships were no longer aligned with who I was becoming or where I was headed.

In business, this has looked like discontinuing work with large clients who were no longer a fit for the direction my company was taking. The tensions and financial impacts were extremely difficult, but ultimately worth it in the grand scheme of my business

In my personal life, these changes were even harder to make – even causing me to feel physically ill at times. But no longer pretending that “everything is fine” has created so much peace in my household.

Lesson Learned: The hardest decisions are often the most transformative. Walking away from what no longer fits – whether in business or life – may feel like loss at first, but it makes room for peace, purpose, and the right opportunities.

What Bold Moves Are Coming for You? 

As I step into my 40s, I’m reminded that bold moves rarely feel easy in the moment. They’re uncomfortable, uncertain, and sometimes downright scary. But each one has shaped who I am today – more confident, more aligned, and more willing to trust my instincts.

If there’s one thing I’ve learned, it’s this: The life and business you want won’t be built on comfort zones. Bold moves create the space for growth. And if you’re standing at the edge of a big decision right now, this is your reminder: You are braver than you think!