Meet Amy Oostveen

We’re excited to introduce you to the always interesting and insightful Amy Oostveen. We hope you’ll enjoy our conversation with Amy below.

Amy, so great to have you with us and we want to jump right into a really important question. In recent years, it’s become so clear that we’re living through a time where so many folks are lacking self-confidence and self-esteem. So, we’d love to hear about your journey and how you developed your self-confidence and self-esteem.

I developed confidence and self-esteem by failing. So many people want to shy away from the failures in life, but I welcomed them. You can only have successes by having failures. Failures, bumps in the road, learning how to navigate problems…..those are all learning experiences. If you spend your time being hard on yourself about the rough times, you won’t be able to learn and build your confidence in the times and moments of success. I remember specific moments of success where I finally had those feelings of confidence and a higher self-esteem. There were times I had to play the part of fake it til you make it. Sometimes people thought I had all the confidence and self-esteem in the world but in reality I was struggling. It’s ok to continue to state facts to yourself while you might not FEEL these two things. There are always things you need to tell yourself as a business owner that will lead you to actually feeling it. Don’t always trust your feelings. Sometimes you just need to put one foot in front of the other to lead you to a confident path.

Let’s take a small detour – maybe you can share a bit about yourself before we dive back into some of the other questions we had for you?

I am the co-owner of Wagging Riders (which currently just got trademarked)! My son and I started this business together during our homeschool journey. We pick up dogs at their house, take them to a place to play, and then drop them all off at their homes. We are a full service business and do all of the work for the owners. It’s insanely rewarding. Dogs love unconditionally and it’s pretty tough to have a bad day with our pups! They are so excited for their bus days. Watching them meet new friends, play with their best friends and take their favorite ride just makes your heart burst with happiness.

My son came up with the name, we started the business having no idea what we were doing! We have learned so much and now have settled into attainable structure, profit and success. We have recently trademarked our name and are currently working on franchising our business!

In the meantime, we will begin to expand our routes Summer of 2026.

If you had to pick three qualities that are most important to develop, which three would you say matter most?

1.) I had knowledge of a 13 year, franchised business when we started this one. It was really fun to see my experience with the business I sold come to life in a completely different industry. Business structure is the same, no matter the industry. Living that was really cool to experience.

2.) I make decisions. Some people tend to think, think, and think some more until they either miss the window of taking action or someone else takes action because they took so long. I have always STARTED. I always think of the Nike slogan: Just Do It. It really is that simple. You don’t have to have everything figured out. You can do that along the way

3.) Resilience. I don’t get nervous when things go wrong or feel like a failure if I failed. I evaluate, learn, apply and move forward. That’s how you build confidence and success.

Any advice for folks feeling overwhelmed?

I reset and KISS. I am a single Mom of two and I pretty much have owned my own business my entire life. I have had so many moments of feeling overwhelmed – SO MANY! If I feel overwhelmed about anything, I reset back to baseline and I KISS: Keep It Super Simple. For example, if I’m feeling overwhelmed about what I have to do in a day, I will reset by sitting at the island in my house. My island is homebase for me and it’s a place where I can think about everything in my life: my faith, my family, my business, etc. I will KISS by first thinking of only the things that I can control. I will consider outcomes I want of those things and then think about how those need to be completed for me to have the outcome that I want. Then, I will think about what HAS to get done that day. I really have to sit in this sometimes because I am a fast mover and an efficient person so I typically think that everything needs to get done. But, I find that when I give myself the time to slowly think about it, there are things that can be eliminated out of the MUST category. When I find those things, I need to process my feelings to accept that it’s ok if they to not get finished that day. Typically at this point, I say, out loud, a strong, simple affirmation of something like: I’m going to do my best. My best is good enough. It will all work out.

At this point, my energy has typically calmed down. Sometimes all of this happens in 5 minutes and sometimes it happens in what feels like 30 seconds. lol Don’t be confused with the fact that you need to take all sorts of time to make this happens. It depends on what works for you and what you personally need at that moment.

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