We caught up with the brilliant and insightful Tawny Ann De La Peña a few weeks ago and have shared our conversation below.

Hi Tawny Ann, thanks for joining us today. How did you scale up? What were the strategies, tactics, meaningful moments, twists/turns, obstacles, mistakes along the way? The world needs to hear more realistic, actionable stories about this critical part of the business building journey. Tell us your scaling up story – bring us along so we can understand what it was like making the decisions you had, implementing the strategies/tactics etc.

Before I became a life coach, I was a direct response copywriter. That means I’m utterly obsessed with using testing data to inform my decisions. The first thing I did was ask friends if they’d like to be coached on a weekly basis for free. That way, I could work out my systems and processes, while also doing a lot of front-end work like building the brand and website. I coached a total of 30 people for one year and before I officially “launched” my business.

I guess you could say the “first year” of my business was about understanding who I wanted to coach (aka my audience), strategies that worked, strategies that didn’t, and optimizing my sales process. That way, when I officially launched, it didn’t feel like it was my first time at the rodeo. I like to call all my (free) clients from December 2021 to July 2022 my alpha clients. And what I learned from my alpha clients was who I liked to coach and who I didn’t like to coach — and that’s how I narrowed my niche to high achievers, founders, and entrepreneurs. About 42-percent of my alpha clients converted into what I call my beta clients. I used my beta clients to really understand the segments that live inside of my target market (aka develop my buyer’s personas). My thinking here was to minimize the cost of paid social testing; if I understand my segments, then I can more easily speak their language, and therefore, convert them.

I had a soft launch in September, when I started charging for my 1:1 coaching sessions. About 58-percent of my beta clients converted into paid clients. By the time I hard launched in January 2023, I was able to launch my business with 8 existing clients, 5 referrals, and a shit ton of testimonials (both written and video).

Now that I’ve mastered the 1:1 systems and processes from a business perspective, I’m making plans to scale. For me, that means creating a group coaching program, including asynchronous courses. By the time I hard launched in January, I had already run four workshops, which I used to base the content I wanna include in my asynchronous courses.

I plan to use the group coaching program as a more accessible product that could potentially lead to 1:1 sessions. But the plan is to increase my 1:1 prices once I launch the group coaching program.

I do, however, want to include the fact that I couldn’t have gotten all of this done without the unwavering support of my wife, who has consistently empowered me to believe in myself and this business. It wasn’t until just this month that I can say I truly allowed myself to work on this business full-time; since I started in December 2021, I was also running my copywriting business at the same time. I’m proud to say that I’m no longer taking projects for that business and that I’m full-time Life With Tawny now.

Tawny Ann, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

I spent the majority of my career (more than a decade) as a storyteller. I began my career as a TV news producer and continued on to become a brand copywriter, then a direct response copywriter. I’ve written for brands like Wolfgang Puck, Dunkin’, Shapermint.com, and more. My work has received recognition like a Peabody nomination, Emmy Awards, and Addy awards. And although I had a successful career as an award-winning copywriter, I knew I had lost the passion I once had for it more than a decade later.

You see, prior to my storytelling career, I had a rocky coming-of-age story. I was raised in a home with cultural values and expectations that didn’t quite align with the values and expectations I developed merely by growing up in America. By the time I was 15 years old, I was a meth addict who got kicked out of honors classes and graduated high school barely scraping by. To top it all off, I was rejected by every college I applied to. My only choice WAS community college. And I think a big reason for my career success is because I felt like I needed to prove to everyone, but mostly myself, that I’m not an addict who was gonna throw it all away at 18 years old. (I’m proud to say that in December 2023, I’ll be 14 years sober.) And the obstacles I had to overcome throughout my life didn’t stop there. I’m not sharing all of this to paint a sad story or to make you feel sorry for me; I’m sharing this to show you why I felt it necessary to become a life coach.

I knew that although I loved copywriting, I always felt like there was more I could do to make an impact than make people buy stuff they don’t really need. If I have this special superpower to make people buy stuff, why not use it for good — for something that can help them turn their life around like I did?

I think most people can agree that there are a lot of ways my story could have ended differently. But I used the tools I learned from coaches I heard on podcasts, self-help blogs and books, and Ted Talks to help me change the way I see the world. There was once a time that I was a really angry person, full of resentment; I fell victim to my own victim mentality so many times. But had I not made that one Google search in 2016, “self-help podcasts,” I really don’t think I’d be the person I am today. It’s the coaching concepts I learned in my darkest times that allowed me to break away from my victim mentality. I didn’t realize it at the time, but the coaching and self-help strategies I learned throughout the years were helping me to better manage my relationships, communication with others, my ADHD, and so much more. Today, I feel the lightest I’ve ever felt. Things that used to ruin my week, now roll off my back. I have much healthier boundaries I can stick to, and I think I’m most proud of the fact that I’ve learned how to do what I WANT, not what I think I’m supposed to be doing or what other people want me to do. I’ve truly learned to live my life for me and no one else. I know what it’s like to pull yourself out of hell and back. I know what it’s like to feel like there’s no hope; like you’re alone in this world. Coaching is what taught me that it doesn’t have to stay that way.

I think it’s my life experiences, traumas I’ve overcome, and career milestones that make it easy for me to relate to high achievers, founders, and entrepreneurs. I created Life With Tawny so that I can help people like me create F-YEAH moments in their relationships, at work, and in their personal lives — ‘cuz life doesn’t have to be that heavy. I do this by helping them “unlearn the bs” (that’s my tagline) that clouds their judgment. This allow my clients to more easily manage negative emotions and behaviors like overwhelm, anxiety, stress, burnout, and procrastination. Really what that means is that I help high achievers, founders, and entrepreneurs build the skill of self-awareness so that they can identify beliefs that limit the possibilities they see for themselves. I work together with my clients to identify actionable strategies that reframe those limiting beliefs into new beliefs that propel them forward rather than hold them back. This allows them to create outcomes/results they never thought were possible.

If I could tell my 18-year-old self that it was all gonna be okay when I grew up — that I’d marry an amazing woman I think of as my best friend, own a sick house, have a dope career I love, and so much more — I wouldn’t believe it. And that’s ‘cuz it’s hard to imagine what you don’t think is possible. THAT’S what I help clients imagine — a different future than they ever imagined for themselves.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

Growing up in an Asian household meant I grew up with high expectations of me and my siblings. And it’s a very important part of my culture to live up to those expectations. It wasn’t until I grew up and left my home that I learned that it doesn’t have to be a bad thing if I don’t agree with the life others wanted for me. It’s okay to agree to disagree.

That’s why I think one of the biggest lessons I’ve learned in life is that just because I have expectations from other people doesn’t mean that they necessarily have to fulfill those expectations. I’ve also learned that sometimes, people just don’t have the capacity to fulfill those expectations and that’s okay, too. We’re all just trying the best we can with what we have. And more likely than not, other people are assholes because something fucked up happened to them either that day or consistently in life.

This lesson has allowed me to stay grounded when people disagree with my lifestyle choices or decisions. It’s helped me be more compassionate and empathetic with people I disagree with. And most importantly, it’s helped me accept myself and others more whole-heartedly.

Have you ever had to pivot?

I’ve pivot in my career so many times. I think one of the reasons I ended up becoming a life coach is because since I was young, I never stopped chasing happiness. So if I wasn’t happy with a job or career, I was never afraid to do something about it. Sometimes that meant starting over completely and taking a lower or lateral role.

I started my career as a journalist but wasn’t happy doing it. I had to work thanklessly long hours and for less money than I made as a server. It was a fun and exciting career, but I felt like something was missing. I didn’t even know what positions were available in advertising until I started dating a graphic designer who was also a web developer. She told me about the type of work she did and the advertising agencies she worked for — and I was hooked.

I scoured LinkedIn for people who used to be journalists and switched to marketing, advertising, or public relations. I asked them why they made the switch and what they liked and didn’t like about their career. This gave me a better idea of whether or not I wanted to pursue a career in advertising and marketing. Once I was sold on the career, all I had to do was get my foot in the door. I applied to every single communications, media, advertising, marketing, and public relations agency in the city I lived in at the time until someone took a chance on me. I rebuilt my career as a junior, eventually went on to lead copy teams, and even spoken as an expert on stages on the subject.

But like I said, I’ve always been a happiness chaser. There came a point in my copywriting career where my personal values no longer aligned with the work I did as a copywriter. I can definitely say that at that point, I was a bit older (closer to 30), so I was less likely to take a risk like jumping careers. But my wife never let me forget my dream of becoming a life coach. I would talk about it like it would happen one day, just not now. It wasn’t until the pandemic and we moved to Tulsa, Oklahoma by way of Tulsa Remote (a one-year program that provides a $10,000 grant to remote workers to move to Tulsa) that my wife asked me if not now, when? And as everyone knows, your wife is often right lol. I had to stop talking about it and start being about it. Four months after we moved to Tulsa, I quit my job, launched my copywriting business, and started building Life With Tawny.

So I guess the moral of the story is — never settle. You get to have your cake and eat it, too. There’s always a way to make what you didn’t think was possible, possible. All you have to do is be daring enough to figure it out, even when you don’t know how. I promise you that what’s on the other side is fucking worth it.

Take a chance on a career you’ve always wanted to try. If you aren’t in a financial position to do that, build the skills you need to pursue that career, while you work your day job. And that’s not the only way to solve that problem. We often think the only option is to get a job. But sometimes, entrepreneurship is better than any job; it can also be the opposite for other people. You’ll never know if what you daydream about can become a possibility unless you give yourself a chance to try.

Contact Info:

• Website: www.lifewithtawny.com
• Instagram: @unlearnthebs
• Facebook: @unlearnthebs
• Linkedin: https://www.linkedin.com/in/tawnyisthecoolest/
• Youtube: @unlearnthebs

Image Credits
I either had a friend take these photos or paid for them. No credit required.