• John Lim

MF 087 : A Single Mom’s Journey Through Entrepreneurship, with Madeline Roosevelt

Updated: Jun 17




Moving Forward is also available on Apple Podcasts, Stitcher Radio, Google Podcasts, Spotify, and Amazon Music.

Madeline Roosevelt is a hair and makeup artist, entrepreneur and single mom to three kids.  She is also a blogger at Up Close with Madi and an ambassador for the Portland chapter of Single Moms Planet, a support network for other single moms.  Today, Madeline will share some great knowledge bursts on moving forward as an entrepreneur, while balancing the responsibilities of being a single parent.

Successes at a glance:

  1. Single mom of three kids.

  2. Entrepreneur: hair and makeup artist, self-employed for over 10 years:

  3. Decided to become an entrepreneur while studying for a marketing degree.

  4. Made a pivot and got her cosmetology license in hair, skin and makeup.

  5. Former chapter leader and Ambassador of Single Moms Planet.

  6. Blogger at Up Close with Madi.

How Madeline gets inspired to conquer the day:

Madeline starts her morning with a positive affirmation to set the tone for her day.  Madeline was inspired by the 21-Day Meditation Challenge by Oprah Winfrey and Deepak Chopra. She also subscribed to John Assaraf’s work in mindset retraining.  Positivity is extremely important for Madeline as she strives to make the most of each day.  On this episode, Madeline shares this affirmation with Moving Forward listeners: “I will conquer today no matter what kind of challenges I have thrown at me!”  Moving Forward listeners, how do you frame your day?  Sometimes we set the wrong tone by negative thoughts or emotions.  Try making a simple pivot thru a positive affirmation.  It may seem silly or uncomfortable at first but saying something positive can shift those negative thoughts which can lead to positive actions.  Give it a try, you have nothing lose!  Take the first step to start moving forward in the right way.


Setback or failure that led to pivot and shift:

Madeline is a single mom of three children: two boys and one girl, ages 12, 7 and 9, respectively.  In that regard, Madeline faces challenges and setbacks everyday, raising three kids while also being on the entrepreneurial journey.  However, this hasn’t stopped Madeline from being innovative or creative.  Even though she juggles many responsibilities, Madeline has made it a point to be an inspiration for other single moms facing similar challenges.  Recently, Madeline reached out to Single Moms Planet, a LA-based organization, designed to provide a network to other single moms.  Madeline saw an opportunity to build a network for single moms in her city and took it upon herself to start a chapter in Portland.  Moving Forward listeners, what challenges do you face?  Are you a single parent who is also striving to do more for yourself and your family?  One of the best ways you can do that is to connect with like minded individuals who share similar challenges; providing one another with ideas, inspiration and partnerships.  Madeline has done this while raising three kids and working full-time as a hair and makeup artist.  She was inspired by a support group in another city and took the initiative to bring it to where she lives.  In doing so, Madeline is providing a portal for other single moms in Portland.  Think about how digital connections and online groups have made this possible.  This is the great equalizer that will allow you to keep moving forward, no matter what challenges or responsibilities you face each and everyday.


Knowledge Bursts:

  1. Resource or cultural experience that inspired Madeline to move forward:

  2. The Go-Getter by Peter B. Kyne (Paperback | Kindle): this book highlights the value of relationship building and going above and beyond customer expectations with a product or service.

  3. How Madeline stays organized and manages her time:

  4. Madeline admits that she struggles with procrastination.  To combat this, she recommends a practice of writing down what you set out to do in a calendar (both paper and virtual). Madeline reminds us that “if you fail to plan, you are planning to fail!”

  5. Favorite app / website / resource or productivity hack:

  6. Simbi: exchange or barter services.  An excellent place to outsource a service (e.g. a blog post) if you are on a tight budget.

  7. Fivver: another great place to find freelancers who can provide high quality work in areas such as logo design, SEO, market research, at very affordable rates.

  8. Busy Bee (Google Play): create a community through your Facebook friends and/or phone contact list.  Ideal if you’re looking for services like child care, ride-sharing or to form a meet-up group.

Support the Podcast:

  1. The Corporate Cliches Adult Coloring Book: makes the perfect stocking stuffer or white elephant gift.

  2. Try out Audible (affiliate link).

  3. Try out Amazon Prime (affiliate link).

Madeline’s Advice for you to Move Forward:

Find a mentor, someone you like and trust but also someone who is at the place where you want to be in your life.  Another way to find inspiration is to explore topics of interest that you would like to learn more about.  Madeline recommends listening to Ted talks and reading articles or blogs from influencers, online.  And as discussed on today’s episode, you can join or create networks to find like-minded individuals, facing similar situations or challenges; to encourage and support one another.  Today, you’ve learned how Madeline Roosevelt created a chapter of Single Moms Planet in Portland.  This is how we forge relationships, make connections and keep moving forward!


Connect with Madeline:

  1. Facebook

  2. Up Close with Madi

  3. Facebook Page

#movingforward #singlemom #hairstylist #movingforwardpodcast #entrepreneur #makeupartist

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