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Conversations with the Inspiring Chelsea Brinkley

Today we’d like to introduce you to Chelsea Brinkley.

Chelsea, please share your story with us. How did you get to where you are today?
I didn’t wake up one day and have this dream of running 2 businesses. I never really thought of myself as an entrepreneur, but now I see it so clearly. I used to work long days in a cubicle at a company where I loved the mission and the people, but led me to be burnt out making someone else’s dream a reality. I was the executive assistant to the chief digital officer and had 15 vacation days a year that I treated like pure gold. Eventually, with the help of a friend who did something similar, I realized I didn’t have to work in a cubicle or office building until I retired to actually live the life I desired. I didn’t want to be stressed out and running the rat race working up the career ladder. Instead, I could do my entire job remotely from anywhere. However, the company I was with didn’t allow remote work, so I started working nights and weekends as a virtual executive assistant to learn the ropes of the remote work world. I had to make sure I knew what I was getting myself into. Turns out, working while enjoying a glass of wine was meant for me. After many months of planning, I made the switch and stepped away from my full-time job and into a remote one with additional clients. Since then, it’s picked up and I have this virtual assistant business where I not only work as a virtual executive assistant to a few select entrepreneurs, but I also coach virtual assistants (VAs) and match entrepreneurs/small business owners with highly skilled VAs.

Somewhere along the way, I decided to combine my hyper detail-oriented and organizational skills as an executive assistant with my extreme passion for travel and start a boutique travel planning business. It’s my creative travel outlet where I’m able to plan adventure trips for folks but also writes travel guides, share tips, and blog about our adventures as my husband and I travel and work remotely from around the world. It’s all been a ton of fun and a lot of work too. There’s no such thing as an overnight success.

Overall, has it been relatively smooth? If not, what were some of the struggles along the way?
Actually getting started and making the leap from my corporate job to doing my own thing was definitely a challenge. I had many supportive family members and friends but also several that urged me to stay with my corporate job. I was told I could travel and explore the world once I retired but for now, I needed to work hard at my career and settle down. It made me question whether I was doing the right thing or if I was going to mess everything up. I eventually decided I knew I was supposed to do this and I couldn’t not go for it.

I think at some point in your journey you’ll have supportive and not so supportive people in your life. If there’s something you know you’re supposed to do, make a plan then go for it. If you’re stuck in a situation where you’re not sure what to do, ask yourself what the absolute worst-case scenario is that could come from you going forward with it and if you can live with it, do it. For me, if it didn’t work out, at least I gave it a shot and could always go back to a corporate job. I didn’t want to regret not trying.

What do you do, what do you specialize in, what are you known for, etc. What are you most proud of? What sets you apart from others?
Helping people is at the core of everything I do and what brings me joy. Sometimes, it’s helping an entrepreneur launch their dream business, assisting in matching an entrepreneur with a skilled virtual assistant so their life is easier, or as a coach to those who are looking for the freedom and flexibility of the remote work lifestyle.

In addition to this, I love helping people explore the world through our travel business. I do this by creating travel guides, offering travel tips, writing about our travel experiences, and customized trip planning.

I think the key is to always focus on serving others, that’s what really matters.

Do you have any advice for finding a mentor or networking in general? What has worked well for you?
Networking and putting yourself out there can be scary at first. Look for opportunities to introduce yourself to others and make connections. When meeting new people, rather than ask folks what they do for a living, I love to ask what they’re passionate about. You’ll get a lot further in a conversation (and it’ll be more interesting) when people are talking about things they enjoy. And hopefully, what they are passionate about is also what they’re able to do for a living.

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Chelsea Brinkley

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