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Chelsy Pillsbury: “Invest in yourself”

…Ohh this is a juicy one! I honestly think I’d keep it simple and do some kind of walking movement. I think COVID-19 has actually started a walking movement since people were so desperate to get out of their homes. Seriously though, walking is underrated. It’s not overwhelming, it doesn’t cause stress, and it’s a […]

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…Ohh this is a juicy one! I honestly think I’d keep it simple and do some kind of walking movement. I think COVID-19 has actually started a walking movement since people were so desperate to get out of their homes. Seriously though, walking is underrated. It’s not overwhelming, it doesn’t cause stress, and it’s a great way to get fresh air. If everyone walked for 10–30 minutes every single day the human race would be substantially healthier. Rather than trying to start movements that are overwhelming, expensive, or time consuming to many people, it would be fun to start one that’s as universal and accessible as walking. Ha! Maybe I’ll start planning it now…


As a part of my series about the women in wellness, I had the pleasure of interviewing Chelsy Pillsbury.

Chelsy is an certified personal trainer (ACE) with a background in applied psychology and an ongoing study to become a Master Practitioner in Neuro Linguistic Programming. She owns Train With Chelsy LLC, a one woman show that helps busy women heal their relationship with fitness, body positivity, and sustainable habits through an extremely personalized 12 week online program. This is more than a fitness program. It is intimate and supportive in ways most online platforms struggle to create- and it’s only going to get better!


Thank you so much for doing this with us! Our readers would love to “get to know you” better. Can you share your “backstory” with us?

Thank you for having me! I’m excited to share what I do because it really is all coming together in a way I wish everyone could experience. I studied Applied Psychology in college and thought I’d graduate, go to grad school, and become a therapist. Instead, I hopped into a toxic relationship after college and spent a few years paralyzed by that. I tolerated it for far too long and when I finally had the courage to cut things off I turned to fitness. I didn’t want to blame other people for my problems or get stuck telling my story as a victim or turn to alcohol to ignore my problems, so when I got into fitness my whole world changed. It certainly didn’t happen in a day, but my physical, mental, and emotional health improved so much that I needed to become a CPT to show others how healing exercise can be.

Once I got certified as a personal trainer I dove right in and made it my full-time job. I filled my schedule with clients of all kinds (from children to Olympic level athletes) and spread myself pretty thin in the process. Gyms will usually take a significant cut of a trainer’s sessions so it seemed like no matter how hard I worked I wasn’t able to properly take care of myself.

That’s when I started investigating the online world. What do programs look like? How do I get started? How do I do it well? I really didn’t want to create another “one size fits all” program at a low cost for people to sign up for and then forget about. For me it’s always been vital I deliver actual transformation, not just information.

I hired a mindset coach to help me heal myself further and the moment I got into that was the moment my whole world shifted. I stopped researching how other fitness professionals were doing things and instead focused on what I wanted to do and what my ideal clientele (busy, motivated women) was searching for. Once I started asking women what they wanted I was able to create something epic.

Fast forward to now and I couldn’t be prouder of the loving, supportive, detail-oriented program I have the honor of leading women through. It gets better and better every week too! That’s been my favorite part of working full time for myself — any time I want to do something I just do it. Taking feedback and taking action is everything.

I’m obsessed with my life now and grateful for the women who trust me to help take their health to the next level.

Can you share the most interesting story that happened to you since you started your career? What were the main lessons or takeaways from that story?

So many interesting and incredible things have happened. I discovered NLP (neuro linguistic programming) which is basically therapy on steroids. It’s very confronting, but it unlocks the mind in ways I didn’t know were possible. Now I’m a practitioner studying to become a Master and I am stoked to start offering “Breakthrough calls” as part of my 12-week program. Doesn’t that make sense? We get so obsessed with thinking workouts and body composition changes will suddenly make us happier, but what about our minds? Combining mind and body work has been my favorite discovery since starting my business and it’s what makes my strategy as a trainer and coach effective. When I had my epiphany of combining the physical with the mental my whole world opened up.

Can you share a story about the biggest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

As if there was only one mistake…gosh, I’ve had a lot of trial and error since starting. As a new trainer I made the mistake of thinking my certification qualified me as an expert. I used to take any client I could get, even if I didn’t know how to help, and that ended up stalling both myself as a professional and my clients trying to see results.

I wanted to help everyone and I came from a good place in my heart, but ultimately it burned me out to take that much and it wasn’t fair to the people paying me to help them reach their goals. Once I transitioned to online training, I made it a point to be serious about making sure my clients and I are the right fit for one another. If I can’t help, I’ll try to provide resources or referrals so the right help can be found.

Another mistake that kind of ties into that one is my burn out. I allowed myself to spread too thin while being underpaid. I learned a lot from that time, but ultimately, I know I can only have the most impact for others when I am well taken care of. I run a very high-quality program at a high cost and it makes it so I can pour everything into each person who joins. I’m able to invest in additional learning, seminars, conferences, and tools to develop my business. I’m able to take care of my personal life very well. And all of this over flows into the relationships in my life both personally and professionally.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Oh my goodness, there’s a list of people. I’ll name a couple if that’s okay.

A girl named Charlotte who worked on the sales team at the first gym I ever joined before I was a trainer. She didn’t “sell” to me in a sleezy way and she made me feel so welcome my first time at the gym. Who knows where I’d be if she hadn’t walked me around and hugged me and helped me feel comfortable getting started.

Another helpful human is Rachel Bell. She’s a genius business mentor for coaches across the board. I went to her summit in San Diego where she then introduced all of us to Allyson Byrd, a brilliant boss babe who helps improve money mindset, and Peter Shaw, an NLP guru who has helped me a ton.

Mostly, though, the support of my boyfriend, Scott, has been unparalleled. He’s seen me go through many transitions emotionally, professionally, and financially. It could’ve been a stressful thing for him to go through with me but he’s always been supportive, proud, and loving. He knows I’m a big action taker and that I don’t like when people doubt me, so he’s nurtured my dreams alongside me and I’ve done the same for him. We’re a power couple for sure and we’re proof that being supportive and on each other’s side is what will conquer all.

Ok perfect. Now let’s jump to our main focus. When it comes to health and wellness, how is the work you are doing helping to make a bigger impact in the world?

My hope is that rather than creating a program that focuses on body image and leaves women saying, “okay, now what?” I can combine physical fitness with mental fitness and create a space where women finish my program saying, “wow, I can’t wait to keep going!” I used to think I needed to make a generic program and sell it to as many humans as possible but instead I’ve chosen to take on only a handful of women at any given time to make sure they’re actually heard and taken care of. I truly believe if health and wellness professionals wore the ‘specialist’ hat more than the ‘jack of all trades’ hat then more people would be better impacted for the long haul. It’s all about sustainability for me. If I can get one woman to join my program and leave feeling more confident, understood, healthy, energized, and ready to implement what she learned to keep her momentum going then I have succeeded in having an impact. Quality over quantity!

Can you share your top five “lifestyle tweaks” that you believe will help support people’s journey towards better wellbeing? Please give an example or story for each.

1. Eliminate the “All or Nothing mindset.” Fitness isn’t all or nothing. It’s consistency and sustainability. Imagine a year of doing 20-minute workouts versus a year of skipping all workouts because you thought you had to devote 1–2 hours of insane effort every time? There is a middle ground, for sure.

2. Be strict with your social media. I unfollow accounts regularly that leave me feeling drained in any way. If I’m comparing myself too much or feeling uninspired, angry, or upset about content I see regularly, I’ll get away from them. Social media is only toxic when we allow it to be.

3. Invest in yourself. Trying to find cheap wellness options will keep you stuck. I learned this the hard way both in fitness and in business. As soon as I was ready to dish out bigger investments in people, programs, software, conferences, and learning material my business, body, and mind improved tenfold. It’s true — you get what you pay for!

4. Prioritize sleep. I know this one is so common and cliché, but for good reason. Any time someone says, “I’ll sleep when I’m dead!” I’m like, “…yes but you actually die without sleep so….” Better sleep improves metabolism, energy, mood, productivity, hormonal balances, so much! Not prioritizing what we know is good for us is self-sabotage.

5. Stop falling for quick fixes and fads. It’s not enough to eat healthy for a month or to work out hard for 90 days. Start looking for people and programs and methods that help build long lasting habits and healthier mindsets. If you try something you know you can’t or won’t do forever, then it’s probably not the right thing to be putting time into.

If you could start a movement that would bring the most amount of wellness to the most amount of people, what would that be?

Ohh this is a juicy one! I honestly think I’d keep it simple and do some kind of walking movement. I think COVID-19 has actually started a walking movement since people were so desperate to get out of their homes. Seriously though, walking is underrated. It’s not overwhelming, it doesn’t cause stress, and it’s a great way to get fresh air. If everyone walked for 10–30 minutes every single day the human race would be substantially healthier. Rather than trying to start movements that are overwhelming, expensive, or time consuming to many people, it would be fun to start one that’s as universal and accessible as walking. Ha! Maybe I’ll start planning it now…

What are your “5 Things I Wish Someone Told Me Before I Started” and why?

  1. SO many business owners are lost, confused, brave people willing to wing it until they got it right. So…wing it. Don’t worry about doing things right, instead worry about doing things. I take messy action until I get it right and I do not quit.
  2. It’s not about me. My business is separate from me. It’s about the women I aim to help. My business revolves around them. So instead of wondering what I want or need or think is fun, it’s important to get that information from my clients!
  3. Do not stop after a couple months! For years I would try something and then give up as soon as it didn’t work out perfectly. I’ve been giving my current program time and let me tell you, the first year was hard, but the second has been epic. I can’t imagine how much better it’s going to get and how sad it would’ve been had I given up four months in when nothing was going right.
  4. Don’t take advice from anyone who doesn’t have what I want or embody what I hope to become. I won’t take financial advice from a friend who struggles with money. I won’t take relationship advice from someone who struggles with relationships. You get the idea. When asking for advice, I go to the people who will challenge me and who I know are speaking from experience.
  5. Never stop learning. Even as an “expert” there will be more to learn.

Sustainability, veganism, mental health and environmental changes are big topics at the moment. Which one of these causes is dearest to you, and why?

Wow. Those are all valuable and important! I’d have to say mental health is dearest to me right now. Without prioritizing my own mental health there’s no way I’d be successful at effectively helping others. Practicing what I preach, remaining consistent with my health, and pressing forward through stress, change, and unpredictable moments has only been possible because of the work I’ve done with my mental health. I’ve always been fascinated with how our minds work, how emotions flow, and what it means to heal how we interact with the world. Psychology, fitness, and NLP have all propelled me further into this topic and proved to me that it’s all related and when we neglect any part of it we suffer greatly.

What is the best way our readers can follow you on social media?

Right on Instagram! @trainwithchelsy — Everything I do is there. It’s simple, accessible, and effective. I can show up on my stories each day so anyone who’s interested in working with me can see what I’m about and what I do. My posts offer valuable information, tips, and tools. Plus, it’s just fun to connect and be part of the nook online that isn’t toxic. I’m all about body positivity, mindset work, and having fun along the way. Come say hi!

Thank you for these fantastic insights!

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