Preppy Consultant Mom on the Street: Courtney Henry

Preppy Consultant Mom on the Street Courtney Henry cover photo

After years of grinding in the typical 9-5 and wanting to spend more time with her family, Preppy Consultant Mom on the Street Courtney Henry knew the time was right to start her own consulting business. Read all about Courtney and how her hardworking spirit inspires many.

Meet Courtney

Courtney Henry is a brand and marketing strategist, podcast host, boy mom, Enneagram 3, and health and wellness junkie. With over 15 years of experience working in marketing and advertising on brands such as Disney, NFL, Planet Fitness, American Cancer Society, Cigna, and Bank of America, Courtney is passionate about getting customers to take note and take action.

Today, Courtney runs Courtney Henry Consulting, a brand and content marketing agency dedicated to helping small businesses make a mighty impact on the world. Courtney is also a wife and mom to two boys, ages one and four. In her spare time, you can find Courtney on the latest episode of her podcast “A Better Way,” running, doing yoga, Irish dancing, or enjoying the Maine coast.

Preppy Consultant Business

When did you first start up your own consulting business, and why?

I always felt there had to be a “better” way. I had spent years working 16-18+ hour days, climbing my way up in major advertising agencies. On the outside, I was successful. But, inside, I was a mess. My health suffered. My relationships suffered. I didn’t feel like I was making a difference. 

Once I had my first son, I realized that there had to be more to life. I vowed to myself that if I had another child, I wouldn’t go back to my traditional 9-5. Somehow, someway, I made that happen. I took a virtual assistant course on a whim in June 2020, while I was four months pregnant, and was up and running with my brand and marketing consultancy a month later. I continued to run it as a side hustle through March of 2021 when I officially resigned from my full-time job.

Consulting and Marketing Strategy

What sort of clients do you help, and how do you build up their brands?

Today, Courtney Henry Consulting has grown into a full brand and content marketing agency specializing in brand strategy, marketing strategy, and content creation for small and medium-sized mission-driven businesses. 

First and foremost, we help clients develop a clear, concise messaging strategy. Consistency is key – especially when you are operating on a small budget. So we help our clients define who they are and why their customers or clients should care to ensure we’re sharing a message that resonates with our ideal audience and is consistent throughout a customer’s journey.

Second, we help clients determine which marketing channels they should be active in and what tactics they should leverage to maximize impact. We believe that small and medium-sized businesses can succeed through organic efforts, so many of our recommendations are rooted in email marketing, content marketing, thought leadership, and partnerships and collaborations.

Lastly, a marketing plan is only as good as its implementation. Most of our clients don’t have in-house marketing support, so we lead the content creation process for them. This includes copywriting and design for everything from websites and social media to sales collateral and event marketing. We also help identify and coordinate brand partnerships and collaborations. 

Also, as a side note, my team is currently built entirely of women – most of whom are moms. I’m realizing that so many of us have moved away from more traditional 9 to 5 roles to find a better way, and I’m proud to be leveraging their incredible talent to build brands worth a customer’s time, money, and energy.

“A Better Way” Podcast

You also co-host a podcast, “A Better Way Podcast” tell us a little more about it, Who is the other co-host, Who do you feature?

I run the “A Better Way” podcast with my friend and co-host, Danielle Drapeau. Danielle and I went to undergrad together at Endicott College, and both lived and worked in Boston afterward. We both have our MBAs, spent our 20’s and early 30’s working like dogs, doing everything we were told was “right” – and yet, we found ourselves exhausted, unhappy, and wondering what we were missing. We both started looking to build something outside our traditional 9-5’s and decided to document our journey and learn from others doing the same.

All of our guests are fellow mompreneurs who are building businesses and families at the same time. We aim to show the good, bad, and the ugly, letting moms know they aren’t alone. We’re also sharing the shortcuts that have helped us and our guests build a better way – be it through marketing tactics, financial planning, mindset, or conscious rest. 

What has been your favorite podcast episode?

We’ve had so many amazing episodes, but I have two favorites:

  • Episode 14Why Rest is the Secret to Success & How to Get More with Deanna Mason: Deanna is a rest consultant who helps busy mompreneurs build businesses that support rest. After having my own case of burnout in a previous agency job – to the point I actually had to leave my role to focus on my mental health – I can’t stress how important rest is for everyone. I wish more moms would listen to this episode and give themselves permission to invest in themselves in this way. 
  • Episode 18 How to Enjoy Your Unique Motherhood Journey with Meghan van Metre: Meghan was actually a client of mine in my first year of business and she has the most beautiful spirit. She holds space for each of us in such a powerful way and I think moms who listen to this episode will feel more peace and empowerment.

Family Support and Lifestyle

Do your family, friends, and husband support you in your business endeavors? How so?

My husband has been my #1 supporter – which is great because I don’t think I would have kept going without him cheering me on in the background. And, my family and friends have been amazing, too. The biggest thing for my family is that they know I tend to be a workaholic, which is amplified when you run your own business. So, they’re extremely proud of me but also cautious because they realize how much time and energy it takes to run a successful business.

Interestingly, my coworkers at my previous jobs have been amazingly supportive, too. They have told me that they always knew I was built for something like this, so their encouragement has meant the world to me. 

How has your work style evolved through the years? Between working, raising a family, and other hobbies?

I’ve had to realize that not everything will get done. But, everything that needs to get done will. It’s still a practice for me, but when I can lean into this, I find more balance and flow in my life. 

Also, I try to remind myself frequently of why I created my own business in the first place. Was it to be working 12-hour days and never have a day off? No. So, I keep that front and center and remind myself that the point isn’t always more money or more clients – instead, it’s about impact, both in the business and at home with my family.

Preppy Consultant Goals, Challenges, and Rewards

What are the biggest challenges and rewards of owning your own business?

I never realized how much of a mental game it is to run your own business. As a result, the biggest challenge has been overcoming limiting beliefs and working to better myself as an individual.

Additionally, your work is never done. There is always more to do. Maintaining the mindset that I “get” to do this rather than “need” to do this has been helpful. When it’s 9:00 am, and I’m still downstairs making my breakfast, feeling the pressure to finish my to-do list before school pick-up, I remind myself that I wouldn’t have been able to have the time with my kids before work if I were in a normal 9-5.

I try to remember when I leave in the middle of the day for a doctor’s appointment that there is no longer stress about “being away from my computer” and “hoping my boss won’t try to call me.” I try to soak in the moments when my team tells me they appreciate me as a leader – these are all examples of why I do what I do and help keep me grounded when things feel hard.

What is your number one piece of advice to other business owners?

Oooh, there is so much I would recommend. But, if there were one piece of advice I would give, it would be to know that no one else has it all figured out. We are all just taking it one day at a time – regardless of if you run a 5-figure, 6-figure, 7-figure, or 8-figure business. Be kind to yourself and know that it’s about the journey, not the destination.

P.S. Having a strong support system can help make this feel easier!

Where can people find your business on social media/ your website?

The best place to find me is at, @courtneyhenryconsulting, and on A Better Way podcast (anywhere you listen to podcasts).

Preppy Consultant Style

Which three words best describe your style?

Sporty. Preppy. Polished.

What are your favorite places to shop?

Old Navy. Target. Land’s End.

Who’s your favorite style icon?

Reese Witherspoon

What’s your best style advice?

Follow what feels good to you, not trends.

What are three things you are most likely to have in your purse at all times?

Goodr sunglasses, Burt’s Bees Lip Shine, a mask.

What article of clothing/accessory would you not want to live without?

Black compression leggings

Which trend would you want to see make a comeback?

Collared shirts

What should NEVER make a comeback?

Crop tops (sorry!)

What’s your best style secret?

A smile! And pearl earrings.

Stilettos or flats?

Running sneakers 🙂 preferably, Brooks

Favorite color for clothing?

Navy blue. Bonus points if it’s plaid.

Preppy Consultant Family

What’s your favorite way to spend time with your family?

At Nana’s beach house in Maine – lots of fresh air, family time, good food, and tons of fun.

What’s been your best family vacation?

As a family of 4, we’ve only done vacations up in Maine – which have been great. While we’re looking forward to traveling further soon (our trip to Ireland was delayed due to the pandemic), we’re loving low-key weeks at the beach right now.

Best parenting advice:

Realize that you can’t control anyone; you can only love them and guide them.

Parenting true confession: 

I don’t like playing with cars, trains, and planes, but I do it anyway because I love my kids’ smiles.

What’s your go-to family dinner?

We love any high-protein, high veggie dish and cook most of our meals at home. When we’re short on time, we especially love sheet-pan dinners, soups, and chilis, or fish and veggies.

What’s your favorite family restaurant?

We love Bar Taco and Bricco – both in West Hartford, CT. Great food and lots of gluten-free options.

Preppy Consultant Life

What’s your favorite show to binge-watch?

Ted Lasso, Ozark, Below Deck.

What’s your favorite beach read?

Anything by Brene Brown or Glennon Doyle.

What song would you dance to when nobody’s watching?

Too many to count – I have the most eclectic taste in music and love doing dance parties with my boys. I love everything from pop, rap, and Latin music to Irish folk, but right now, my boys and I are really enjoying songs from Koo Koo Kangaroo.

If you could go shopping with anyone from history, living or deceased, who would it be?

My dad who passed in 2015. I think family connections and traditions are super important – I was known as his “shopping buddy” and would love to have the opportunity to take another stroll through the aisles with him.

What’s at the top of your travel bucket list?

I’ve already been to Ireland and England, but they are #1 on my list to go back to. I’d also love to explore the Mediterranean coast and make a visit to Australia someday.

What’s your favorite way to unwind at the end of a long day?

Read, meditate, and spend time with my husband.

Family and Business Life

We love Preppy Consultant Mom on the Street Courtney Henry’s love of helping other mom-entrepreneurs through her podcast or consulting business. She exudes passion throughout all areas of life, whether through her business, her podcast, or hanging with her family. Be sure to check out Courtney on Instagram at @courtneyhenryconsulting.

And for more interesting and inspiring moms, be sure to check out FamilyApp’s Mom on the Street page!

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