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Lindsay Yaw Rogers of Raw Strategy: “Understand your mission and work from there”

Understand your mission and work from there. I made the mistake of focusing strictly on execution and production of work, and it landed me in a place where I was not attracting the clients I enjoyed working with. Instead, focus on the impact you ultimately want to have, then work backwards to figure out the “how.” […]

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Understand your mission and work from there. I made the mistake of focusing strictly on execution and production of work, and it landed me in a place where I was not attracting the clients I enjoyed working with. Instead, focus on the impact you ultimately want to have, then work backwards to figure out the “how.”


Many successful people reinvented themselves in a later period in their life. Jeff Bezos worked in Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder, to an actor to a Governor. McDonald’s founder Ray Croc was a milkshake-device salesman before starting the McDonalds franchise in his 50’s.

How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?

In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.

As a part of this interview series, I had the pleasure of interviewing Lindsay Yaw Rogers.

Lindsay Yaw Rogers is a brand story strategist, and owner of Raw Strategy. She coaches entrepreneurs, athletes, and business owners on how to leverage their personal and brand story to stand out, position themselves as a leader, and inspire authentic relationships with their customers. Grab a free guide on 4 surprising ways to use stories in your marketing here.


Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I am a storyteller. It started when I was 3 — my parents took our family of 6 on a sabbatical to some of the most remote places in the world — trekking across Kashmir, sailing in Tonga, and visiting tribes in Kenya. Rinse and repeat in 1988 when we traveled around Europe in a VW van stuffed with road bikes, hiking shoes and baguettes, and we met some of the most fascinating people along the way. These moments, these memories, were seared into our cells and would inform how I perceived experiences from age 3, on — normalcy was the enemy; people and their stories were the gift. These trips embedded something in how I see and approach life’s dynamism — stories have the ability to shape and impact our lives and our future.

We grew up in Aspen, Colorado, and in the midst of those trips, I was a student, a friend, a nature lover, and a ski racer. Starting at age 13, I traveled the country, then the globe ski racing mostly speed events (downhill and Super G) which means I’m most comfortable at speed, and in the cold. I formed relationships with people from all over the world, and helped me understand that people are my fuel as I loved them a much as I loved the idea of racing at the elite level. That has formed much of how I have pivoted my business — helping people understand that bravery and confidence in their story will ultimately cause far more impact and stronger relationships than if they chose not to share their story.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Tell the story of the mountains you’ve climbed. Your words could become a part of someone else’s survival guide. ~Morgan Harper Nichols

I reread this quote daily as it gives me license to feel that what we go through in life, relationships, and in business, is worth it — if not to us at the moment, it will be to someone you connect with in the future. So, share the stories, share your insight, reflect on what you’ve learned and be honest and transparent as they could, quite literally, become someone’s guide to overcoming their own monster.

You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much? If you can, please share a story or example for each.

  1. I believe that you never learn less. It is a concept my dad taught me that has allowed me to obsess over my craft and not feel like it is wasted time. It allows me to take miniature tangents in life that always beget so much knowledge, insight, and experience that I lean on often, in part because I’ve come to understand that a narrow path means a narrow perspective.
  2. I strive to be more interested than interesting because people remember what questions you asked them, not how much you shared about yourself. Recently, I was messaging someone I viewed as a mentor on Instagram, and I was sharing how she inspired me, and why. I asked her a few questions that were out of the norm, expecting nothing in return as she has hundreds of thousands of followers. She wrote back and said nobody had ever asked her that — which spurred a longer conversation, an interview, and now it is becoming an article on Business Insider.
  3. I believe that the back of the statue matters. In other words, all the unsexy stuff that happens on the backend of your craft, of your business, and in your life — it matters. It matters how you communicate with your audience, your employees, and your peers because that will become your legacy. The front of the statue — the side everyone sees — is just the byproduct of the precision of the backend of your unfun stuff behind the scenes. This, again, harkens back to relationships — take care of the ones nobody will see and they will take care of you.

Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?

I’ve never wanted a boss, so I’ve made decisions along my career to make sure that doesn’t happen — or if it did, it was brief and I extracted all the knowledge I could from the experience. In that, after college, I landed magazine editor jobs at Outside and Skiing magazines. A few years in, I ached to travel, so I launched my freelance career — which took off. I traveled across the globe as a freelance journalist for Outside, National Geographic Adventure, Skiing, MSNBC, Yahoo! and many more. Among others, I traveled to Annapurna in Nepal documenting Ed Viesturs’ final 8,000m peak; to northern Norway retracing the steps of Jan Baalsrud, a forgotten war hero; to Utah where I was buried in a simulated avalanche to report on the physiological repercussions of oxygen deprivation and hypothermia; to Canada, Chile, India, and numerous other locations across the world. In that time, I learned what mattered to people and why. I learned how to use language to connect, and how to translate highly personal stories into universal truths. In essence, I learned how stories can transform people.

At a certain point, I began being approached by larger brands to build story-based content that would resonate with their audiences on a deeper, more personal level. I worked with MSNBC, Yahoo, NBC on several Olympics projects, Twitter, Toyota, Aetna, and many more on building sophisticated and strategic content programs and it was exciting, and I loved it — at the beginning. From the outside, it looked like a fabulous and lucrative career — and it was for a while. I was traveling to incredible places all over the world. I was interviewing fascinating people. And working with iconic brands the world was familiar with. But I was trading time for dollars, and not building a business I was proud of, nor a legacy I could point to for my kids. Plus, I was away from my 2 young children and the guilt was overwhelming as I felt I wasn’t doing anything well — working, nor being the mother I wanted to be.

And how did you “reinvent yourself” in your Second Chapter?

So, in 2019, I took a break, stopped traveling for work, and started taking a very hard look at what I wanted in my life, how I could leave a lasting legacy that changed people for the better. I took courses, hired coaches, read every personal development and business book on the shelf today, and I realized several things. First, I wanted to help people, not just brands. I wanted to give them a holistic transformation in themselves, in the stories they told the world, and how they were perceived by others. In that, I came up with a brand story framework for entrepreneurs, coaches, athletes, and businesses that allows them to discover their own story that is aligned with their values and strategic business goals, and share it with the world so they can stand out, and build movements. That is what Raw Strategy is all about today.

Can you tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?

This may sound trite, but I was sitting in a hotel room in Washington DC, exhausted from working all day, and I called my daughter to tell her good night, but also that I had to stay an extra day to do some more work. She started crying on the phone, so disappointed I was going to miss another soccer game, another dinner, another book at bedtime, and she refused to talk to me. I started crying, and decided this life that looked so successful on the outside wasn’t worth it on the inside — she was. And so were my husband and my son. If you don’t have your relationships, you have nothing. So, I decided to build a sustainable business that allowed me the flexibility and freedom to share valuable time with my family and friends while investing heavily in the growth of others. In that time, I realized that what my business was not giving back to me was that sense of discovery and service — how I could develop something strong to change someone’s life for the better.

What did you do to discover that you had a new skillset inside of you that you haven’t been maximizing? How did you find that and how did you ultimately overcome the barriers to help manifest those powers?

Up until this point, I had worked with larger corporations and teams within those organizations. And, I was always the hub of the content wheel, project managing the process of content production so my communication had to be excellent. However, when I pivoted my business to work in more of a teaching and coaching capacity, I found that I was far more influential, far more compelling, and had a far greater impact on those I was speaking with because it allowed me to delve deeper into their challenges, empathize with their struggles, then put systems in place to solve them right then and there. With larger brands, it is harder to be as effective in a short time frame as I’m able to be with small and medium-sized businesses, or even individual people.

The other thing I discovered is that, over time, I had created a process framework that I used with clients that made the projects immensely successful — but it was in my head. As soon as I catalyzed that into a step-by-step roadmap to bring clients through, I saw immediate results and I wanted to make sure smaller companies, and entrepreneurs had access to this framework.

How are things going with this new initiative? We would love to hear some specific examples or stories.

So tremendously great! This year has been a foundational year for my business, and I feel fortunate that it has also brought in so many clients that I am thrilled to be working with. With my brand story framework, I have attracted people who are in the midst of a major pivotal moment in their life or business, or at their inception, along with several large and thriving brands. And the process I bring them through tends to eradicate their fear of change, fear of not being successful, and fear of not having meaning and purpose in their lives and in their businesses.

For example, I’m working with a Muslim woman now who is launching a new business training and coaching families on how to keep the Muslim faith embedded in their children’s lives. She has not only taught me so much about her faith, but she has had massive epiphanies about her business, and her life, that have massively transformed how she sees her future. That, to me, is the greatest gift a client could give me.

I’m also working with a professional athlete and major influencer in England who has arrived at a point in her career where she wants to pivot her message, pivot her offering, and pivot how people perceive her, so we are working together massively overhauling her personal brand story, and documenting every step of her journey together through IG lives, Clubhouse rooms, and social posts. It is so much fun!

I’m also working with a major brand in the construction space creating a brand anthem video that is going to break with so many norms in that industry — we are hoping to disrupt the status quo in an otherwise very conservative space.

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?

There are a few people who have become mentors for me, all of whom I owe a debt of gratitude toward as they have unknowingly guided me down this new path. Due to the constraints of Covid, I lost my biggest client in early 2020. During the lag as I picked myself back up, I started listening to podcasts and reading books by Brendon Burchard, Amy Porterfield, Tim Ferris, and Seth Godin — all of whom have radically different styles, teach on radically different topics, and have radically different skill sets. But each one provided a tiny step I could take to regain my footing as I pivoted my business.

Can you share the most interesting story that happened to you since you started in this new direction?

People keep finding me, and it surprises me every time. As I shared up higher, the biggest surprise I’ve had is reaching out to a huge influencer, and having them respond so favorably that we have partnered on guest posts for major business publications together. When in doubt, don’t be afraid to ask — you might just be surprised with the answer.

Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?

This is not a moment in time as it is a perpetual problem that all entrepreneurs face on a continual basis because you are always creating and innovating new things. That said, a few years ago, I had come off of a huge, all-consuming project and I was struggling to land projects that I was inspired by (I had plenty that just paid the bills). I wondered why, what was wrong with me, my approach, my style, etc. I happened upon a few books (High Performance Habits by Brendon Burchard) and two programs (one through Seth Godin, and one through Bo Eason) where I honed my skills articulating stories, as well as nailing down the lessons and reasons for my own journey, then encapsulating all of my experience into a specific and results-driven framework. In that time, I also worked on future-casting what I wanted my own business to look like, and how and who I wanted to be in that. Once I had a clear visual of my own mission, and the mission of my company, from there it was less about me, and more about execution.

In my own work I usually encourage my clients to ask for support before they embark on something new. How did you create your support system before you moved to your new chapter?

I’ve struggled with this because I’m intensely independent. But, in the past 2–3 years, I have joined several mastermind groups that have allowed me to let my guard down, learn how to grow my business in new ways, and accept incredibly valuable feedback on how to do that. It has given me a massive boost of confidence in scaling my business.

Starting a new chapter usually means getting out of your comfort zone, how did you do that? Can you share a story or example of that?

I love risks. I grew up ski racing downhill, and my dad was an entrepreneur who always instilled the idea of exploration being the root of all great teachings. In that, I don’t find myself intimidated by being out of my comfort zone, but that doesn’t mean I am always IN my comfort zone. I’d say one of the ways I am frequently out of my comfort zone is by trying to teach to new audiences every month. Whether that is on Facebook teaching someone else’s FB group, or at a conference or on a podcast, I have had to force myself to come off as confident and fully in control when I sometimes feel completely out of place. To offset that, I typically overcompensate and tend to be overly prepared for anything!

Fantastic. Here is the main question of our interview. What are your “5 things I wish someone told me before I started leading my organization” and why? Please share a story or example for each.

  1. Understand your mission and work from there. I made the mistake of focusing strictly on execution and production of work, and it landed me in a place where I was not attracting the clients I enjoyed working with. Instead, focus on the impact you ultimately want to have, then work backwards to figure out the “how.”
  2. Be prolific from day one. As in number 1, I spent years focusing on executing on large projects, but didn’t think strategically over the long term so wasn’t producing content across multiple platforms that allowed others to see how I work, how I think, what frameworks I use, etc. Being prolific pays off as it allows people to find you more readily, trust you, and then ultimately buy from you. Since becoming a guest poster on Business Insider, Medium, Thrive Global, and numerous large Facebook communities, I have seen a huge uptick in revenue.
  3. Position yourself as a leader. Building on number 2, once I pivoted my business, I began to see the importance of positioning yourself as a leader in your own space. So, get on podcasts, write guest posts, and teach to other people’s audiences as frequently as possible to be seen as a leader in whatever industry you’re in. That means you have to build it into your schedule every single week.
  4. Never burn a bridge. Nobody had to tell me this, but it is something I live by as I firmly believe that relationships are the root of all happiness and success in life. Even if a client isn’t as enjoyable as you wish, treat them as you wish to be treated, and it will come back to you tenfold. I had an experience a couple years ago where I was tapped to be the content lead for a large national brand. I declined the job offer, but sent them a document outlining several key strategies I would have used had I accepted the job. That company has not only become a client since, but has referred several clients as well.
  5. Accepting help is a key to growth. Nobody is their strongest alone. My hubris when I was young made it so that I had a bullheaded mind of someone who didn’t want to admit that I didn’t know anything. I’d fake knowing anything, and I believe it cost me a couple years of growth in my business. Instead, adopt a learner’s mindset and know that asking for help is what will skyrocket your personal and professional aptitude and ability to grow.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

I want people to find confidence in themselves through discovering the most compelling parts of their story — then sharing it with others as a social contribution. The primary way we all learn is through knowledge transfer, and sharing stories is the way our brains are designed to receive that information. I suppose Oprah made a career out of encouraging people to share their stories. I’d like to piggyback on her movement and allow people in the business space to find the confidence, and key paths, to sharing their insight as a way to guide others on their journey.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them. 🙂

At the moment, I’d love to sit across the table from Tim Ferris or Guy Raz. I’ve been studying how Tim Ferris asks questions in his podcast interviews as he is the master, and therefore tends to get unique answers out of his very practiced guests. Guy Raz: Another master interviewer, but his style is so different than Tim Ferris’. What I appreciate in Guy Raz is his humility as it transcends the questions and makes the interview feel like you’re sitting across the table from whomever he’s interviewing. I’d love to sit across from both of these guys and ask them about their interview process, and how they’ve honed their craft of becoming, quite literally, a craftsman of questions.

How can our readers further follow your work online?

Instagram: https://www.instagram.com/rawstrategy/

LinkedIn: https://www.linkedin.com/in/lindsayyaw/

Website: https://www.rawstrategy.net/

Thank you so much for sharing these important insights. We wish you continued success and good health!

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