An Interview with Stylist Maegan Watson of My Dear Watson

To say Maegan Watson could help you overcome your wardrobe challenges is an understatement. As the founder and CEO of the personal styling firm My Dear Watson, Maegan takes an inside out approach to building wardrobes for executive women. She styles for desired feelings, goals, expectations and life changes to create wardrobes that help clients feel the way they want to feel and love the way they look.

Read on to learn more about Maegan and her company – and to discover the unexpected investment that gave her the best return in her business and life.


What drew you to entrepreneurship over going the more traditional path of working for someone else?

There is part of me who always knew that entrepreneurship was the best fit for me.  I remember going to the career fair in college and thinking – this is not for me.

One of my greatest strengths is strategy and vision. It’s easy and exciting for me to come up with new ideas and solve problems creatively. As an entrepreneur, I get to exercise this strength all the time.  Most importantly, I always wanted to be a mom and have the flexibility to work and focus on my family. I have a toddler now and entrepreneurship has given me the exact work-life integration I always wanted.


How would you describe the work you do?

I support female leaders with image and wardrobe. I've been a stylist my entire career, even throughout college and graduate school, and I found a major flaw in the way women were getting dressed and leveraging their visibility. As women, the number one thing that keeps us from speaking up or living the brave life we deserve is appearance and body image. This topic has been researched for decades and the results are always the same: the way we feel about our appearance can create the cold rush of shame or the supportive push of self-acceptance and love. I knew I had to shift the way the world uses personal styling to empower more women to harness how brave and beautiful they are to change the world.


What does a day in your working life look like?

I start work around 9am by checking in, reviewing my goals and responding to emails. Most of my days are spent doing video styling sessions with clients and potential clients. We are a full-service boutique so we do all of our clients shopping and styling. That means we do a ton of online shopping and reviewing lookbooks with the team.

What hats do you personally wear in your business and where do you have support?

I wear two main hats: sales and service. Every lead that comes through our door talks with me. I have a team of stylists that service clients, doing the shopping, styling and supporting alongside me, but I also have my own book of clients that I work with exclusively.

I have an amazing assistant and my husband is our COO so he ensures that our systems are running smoothly. We have a phenomenal sales coach – a coach is a must! I have vowed to have one every year that we are in business. We also have 3 to 4 virtual assistants that do various things like copywriting, automation, lookbooks, email marketing and I'm sure a million other things I'm not thinking of.

What makes you uniquely suited to do the work you do?

I'm an exceptionally sensitive person. This certainly comes with its challenges but it makes me particular gifted at understanding someone at a very deep level. It also makes me sensitive to colors, patterns, textures and fits, which positively impacts the visual aspect of my work. We don't create images and plant them on our clients. We extract the core of who they are and ascribe visual attributes to the qualities that make them unique. I'm blessed to have the empathy to allow people to open up because it is a vulnerable and powerful process to experience. The end result is unlike anything I could imagine.


In those first few months of business (or maybe even years), what were your biggest challenges, real or self-imposed?

The biggest challenge in the beginning was constantly questioning the efficacy of our work. As our programs evolved and eventually became 100 percent virtual, I was always worried that the program would have some fatal flaw. It took a lot of faith to go implement them anyway and allow the kinks to work out gracefully.


How did you overcome those challenges to find your version of success?

I have to be very conscious of my mindset. Working on my faith in the universe is really what gave me the space to allow things to unfold. The early months were exceptionally difficult but in retrospect they didn't need to be. If you can find a way to stop worrying, then do it. Everything is going to work out in your favor even if it’s not what you expected.


What drives you to continue giving your time and energy to your business, even when it’s hard? Put another way: what’s the motivation behind what you do?

I'm motivated to keep pushing through the hard times because I genuinely love what I do. I experience so much joy when I get to unveil a new wardrobe to a client. I get so much drive from the positive feedback and from witnessing the transformation.

I'm also motivated by the vision I have for our team. Scaling our business has been challenging but I'm proud of the culture we are trying to create, one with good pay, flexibility and [the chance to] work from home. I want to grow so I can give more people the opportunity to work with us.

The last motivation is financial freedom. It's such a gift to truly have unlimited income potential. Yes, not getting a paycheck every two weeks can be scary but there is an incredible financial upside to working for yourself.


Let’s talk about failure. How have you learned to deal with failure in your life as an entrepreneur?

Failure stings at first but the more times you fail, the easier and easier it gets. I've had to learn to laugh at it. I've had some major failures. I started businesses that didn't work and made decisions out of fear that derailed our progress but they all led me here. Yes, I would erase some of them if I could but I can't do that so laughing about it softens the blow. Plus as Marie Forleo says "everything is figuroutable." I can't tell you how many times a week I use that phrase to ease some tension.


What’s the best investment you’ve made in your business or self-development so far? What’s the next investment you want to make?

The best investment I ever made in myself was yoga teacher training. I did it for myself without the intention to teach. The best investment we've made in the business is hiring our first coach. It was an integral part in our success.


What is your long-term vision for your business, and life?

My long-term vision is to be a world-renowned virtual, personal styling boutique. I'd like to expand to Canada by 2018 and Europe after that. I have a vision for a 5-person leadership team that will give me the flexibility to work on a long-time passion project with my husband.

What advice do you have for women who are working hard to get their business off the ground and who fear failure?

The world needs what you have to offer. We are not given the vision for something without the skills, talent and drive to make it happen. It's truthfully so easy to make money when your intention is to serve other people. You are destined to follow your calling – and if you were called to be an entrepreneur, then stop worrying about having to get a job. It's not part of your path. Lastly, be confident in what you have to offer. There is immense power in being a woman who stops selling herself short. You got this!


Is there anything else you’d like to share with readers or any requests you have of them?

My request would be to take one action step toward your goal after you read this interview. We all need support – and I need a ton of it. If your dream doesn't seem possible, then you may just need a loving nudge or a fresh set of eyes on your vision. Make a call, send an email and be open to the possibility of things working out when you enlist the support you need.


Where can my readers find you and connect with you online? 

The best place to find me is at and the best way to connect with me is via email at I also have a complimentary gift that walks women through some of the most transformational parts of our signature program. If you're interested in having a closet full of good-to-go outfits that transforms the way the world receives your gifts, then I invite you to click here and gain access to that free gift immediately.