My Good Woman
Ep. 28 | CEO or Bust: The Rough Road to Becoming Your Own Boss
Dawn Andrews:
Welcome back friend to another riveting episode of My Good Woman, where we don't just dream about being the boss. We actually become the boss. Even if that journey looks more like an episode of Survivor than Sex in the City. Fasten your seatbelts, because we're about to dive into the nitty gritty of being the driver of your own destiny.
Because it's the ride that makes it all worth it.
Hello friends. Welcome to My Good Woman, the podcast for new and future Female Leaders. I'm your host, Dawn Andrews, a happily married hockey mom and the founder and CEO of Free Range Thinking Business Strategy Consulting. Grab a seat at the table with me each week for candid conversations with culture shifting, glass ceiling busting, trailblazing, women leading impactful enterprises. We discuss what makes them tick, how they get it all done, and actionable strategies to help you lead with confidence and grow the visibility, reach, and revenue of your business. We're classy ladies, but we don't bleep the swear words, listener discretion is advised.
If you've ever caught yourself, daydreaming about calling the shots without a soul to answer to, except maybe your cat. Then buckle up because we're about to take a detour from Dreamville and land smack dab in the middle of reality city where you trade your business fantasies for a CEO nameplate.
In this episode, you'll learn the unvarnished truth about the roller coaster ride of entrepreneurship. The lessons I learned from my own journey to becoming a CEO. And how to figure out if you're ready to trade your corporate ID for a shot at being your own boss.
Before we dive in. If you already know that launching a business is on your horizon. I've got a special gift for you. If you want to figure out if you've got what it takes to be a trailblazing entrepreneur, take our fun, insightful quiz to uncover your entrepreneurial spirit. Discover, whether you're a Born Boss or a Mindful Maven.
And get tailored advice to guide your journey. Click the link in the show notes or head over to DawnAndrews.com/BizQuiz to get started. Take the quiz now, because your next big leap might just be a quiz away.
Now let's get to the real, real.
Act one. Backstory.
Picture this. There was a marketing director in the glamorous world of entertainment. Life was like a glossy magazine spread until one sunny day I was served up a pink slip sandwich with the SIDA. What the hell do I do now? You might say I was thrown into the deep end, but that's giving the deep end a bad name. It was more like an ocean of uncertainty with no lifeboat insight.
I got laid off. And I wasn't really sure what to do about that. I'd reached out to a coach, knowing that layoffs were happening in my company and might be coming for me. And I took away some great advice. And in those coaching sessions, I realized I wanted her job. But I was unprepared, untrained,
And I didn't really know how I would turn that into a profession that made me money.
What I was clear about is that I did not want to go to work in another company. I wanted freedom and flexibility. I remember driving to work in another crush of LA traffic, wondering what it would be like to run to the grocery store when everyone else was working. And honestly friends, I am not a big fan of going to the grocery store.
But I just liked the idea of being able to work when I wanted to work and take time away when I wanted to take time away. To not feel like I had to fight the sea of humanity every time I wanted to get something done. I've always been a city girl. I love working in very urban environments with a high population.
But I think I was getting to a point where I just didn't want to struggle like that anymore. I wanted the flexibility to be with my future kids. I was not yet a mom. And to still work without struggling through a corporate Workday having to be somewhere at a certain time.
And I had a little family history on my side. My grandparents were entrepreneurs. They were the O G chip and Joanna. starting out as a young married couple, they bought a fourplex apartment and renovated each unit as they moved into the next. They were micro moguls.
And maybe you've heard this phrase before when people are talking about work. Like, even if they're complaining about their job, they might say,
Well, it's better than digging ditches. That's what my grandfather did next. They sold the apartment to buy a backhoe. And my grandfather literally started digging ditches for a living. People would hire him and the backhoe for a day of work. Over time. He added more machines, more people and built a large plumbing, heating, cooling, and contracting company.
That had a hand in building a majority of the Northern California town I grew up in and the surrounding areas as well. It was where I got my first job at 13 years old. while I was working there, my grandmother was over my shoulder telling me I could do or be anything I wanted to be.
Which is a kid sounded great and as an adult was completely overwhelming. By the time I hit my thirties, I still didn't know what I wanted to be when I grew up. I just knew I wanted to be able to make something myself. To put my heart and soul into something that was meaningful to me. And I was naively confident enough to take the leap. Start a business. And had no clue what I was in for.
Act two. The entrepreneurial struggle is a real.
You know, in the beginning that first year there was a struggle. Oh, honey, was there ever a struggle? It was like, I was trying to build an empire with a toothpick and bubblegum wrappers. In fact, I was so overwhelmed. I didn't even know I was trying to build an empire. I was just trying to figure out how to survive and stay motivated.
And to manage the tangled yarn ball that was my excitement and my fear in equal measure.
Frank and I had been married for three years. We were first-time home buyers. He had a steady job, but we needed both incomes to make it all work. This is Los Angeles after all. So I jumped into entrepreneurship like a cat on a hot tin roof. I was scrambling, struggling, and occasionally face planting.
Picture me like what claws out, like sliding down the roof, trying to hang on. Starting this business felt like the ultimate game of dress up. I felt like I was business Barbie.
It was 2002 Skype, zoom, social media didn't exist yet. It was me. An old Mac tower, computer. A hot garage and a rotary phone. For all you youngsters out there. A rotary phone is the phone with a dial on it where people would stick the pencil in the circles and you'd have to dial the phone. Or your finger. If you don't have long nails. I had no idea how to run a business. It was tough. No sugarcoating.
I had no MBA.I had a little bit of cash in the bank. Barely five figures. And no clue. At that time, the world of coaching was brand spanking new. It hadn't even gotten to the point where people were making fun of life coaches yet.
And I was enrolled in courses to make me a great one. But it would take three years before I was done with school and I needed to make money now, which is a great motivator.
Frank. And I cleared out our uninsulated old 1920s garage space to use as an office. It's the kind of garage space where you walk in and you can immediately smell the dust. And there was no insulation. The walls were bare. It was simply stucco and studs. And it was hot as.
I was surrounded by Christmas decorations, smelly hockey equipment, and those boxes of old clothes and books that you move from apartment to house, to apartment and never seem to get rid of.
We hung a curtain as a wall to hide most of it, but it was rustic at best. It was not Instagrammable. And I thank God Instagram didn't exist to document the jankyness of my situation at the beginning. It's hard to feel like you're a professional when you're sitting in the middle of a garage with hockey equipment.
I was using that old phone I talked about because I thought it looked cool. It was a bright blue phone and really big and chunky. It took up a huge portion of the desk, but for some reason, I felt like it was inspiring. It was filled with possibility for me.
And just to have a phone in the office. I had to drag the phone cord From under our main house into this outer garage and the deck in our backyard, just to get a phone into the office. . covered in dirt
Those first few years. We did everything to save money and watch our expenses. I was doing everything myself. We also took on some debt that would take nearly a decade to pay back. So here are a couple of lessons. If you're considering entrepreneurship. Lesson one even if you feel like an idiot. Ask for help.
Trade with someone, ask questions, get a mentor, get a coach and shorten the distance between taking the leap of starting a business. And having your business take flight and make some money. And then when it comes to the debt, it is worth betting on yourself and going into debt, if you have a guide to help you make smart decisions with your cash.
I did not. They were my best educated guesses. And looking back, having a solid coach or mentor would have made all the difference. We may still have been in the same debt. It may still have taken the same amount of time to pay it off. But where I put the money to grow and to support myself would have been better utilized.
So here's what the day-to-day looked like.
Each day I would get up. Shower put on my work clothes And go into the sweaty little office in the back. Not knowing what the heck I was supposed to be doing each day. It was like a Stranger Things episode with the upside down, one side was a busy office life and a full to-do list.
Which is the way things used to be when I was working in corporate. And the other side, the upside down was wandering in a dark forsaken wilderness searching for purpose in a hot garage.
One of the saving graces at that point was that I had been able to turn part of my previous corporate job into contract work. My mentor, Leanne helped me to do that. So I had some cash scraps to get me started. And you can look forward to my conversation with my mentor Leanne in a future episode.
Then it was time to really reach out and let people know that I was in business and I became a mail merge power user. And sent physical snail mail to everyone. I knew announcing the business. That was me opening my literal address book, not contacts on my iPhone. And putting them all in the computer and writing individual letters to over 400 people.
And at that point, I didn't know what to say. I mean, obviously, I said I was launching a business. I did have a business name and an idea of the coaching I was offering.
There was no marketing. There was no positioning. There was no packaging and pricing. It was just basically a plea to be hired. And at the time. I was very proud of those letters. Each one that went out felt like I was one step closer to the future I was dreaming of. and after 400 letters. I finally got a bite.
My first client was a lovely, gracious, thoughtful friend who was doing something similar. She was leaving her job to start a business. And I was about five or six steps ahead of her. So she was the perfect person to coach because I had a lot to offer. And we both had a lot to learn.
In my first year of coaching. I made a cool 20 grand with five clients. And let me tell you. It felt like I had earned every single penny, the hard way. In fact, if there was a harder way to start a business, I'm not sure it exists.
Act three. Rising from the ashes.
So here's the thing about tough times. They either grind you down or they polish ya up.
During those first several years, I became a voracious reader and learner. I continued to get better at serving my clients as a coach and get better at running my business and marketing to people. And year over year, the money increased. Google and I we're super tight.
I read books. I read magazines. I talked to people. I would go to networking events, even if they weren't necessarily the most appropriate for what I was doing. If you'd like a list of my top reads for starting a business, check out the show notes.
I enrolled in telecourse trainings with the early versions of online marketers Promising to help me 10 X my revenue, or find my ideal clients. Some of those telecourse is, were brilliant and some were duds and all of those telecourse trainings now have turned into online masterclasses webinars, et cetera.
But they used to be done on the phone. You would dial in. And you'd listen to an hour and a half long phone conversation. And buy, based on that conversation,
By year four. Things really started to shift. And I just want to say. It was year four for me. It does not have to take that long for you. That was me not knowing what I was doing and figuring it out as I went. So if you're one of those die hard people that wants to Maverick it and do it on your own.
That is great, but the quote that comes to mind is if you want to go fast, go alone. If you want to go far, go together. I would actually disagree with that quote, if you want to go fast and far, go together. Especially when it comes to business. So in year four, I was hustling, learning, growing, and finally.
Finally I was earning. And it was a big turning point moment because I was also bold enough to reach out and get hired by a Hollywood talent management company.
I was six months pregnant with my first son and waddled into their office to coach the founder and his execs based on a cold call I made to their offices. And if that version of me had looked back. Three or four years to the person that walked into that dusty office by herself. We wouldn't have recognized each other.
That's how much things had grown and changed in such a short period of time.
this game-changing cold call. I had rehearsed and fretted about. It took me almost two weeks to make it. I was rewriting the script of what was a three-minute conversation repeatedly.
So maybe the baby bump was lucky, but by then I had coached more than 150 clients and I was getting great results. I just hadn't ever made a real cold call before. Those letters that I sent out were about as close as it got.
That management company I refer to now as my patient zero. The beginning of the spread of the virus. Through the founder I met clients that I still work with to this day, more than 20 years later. We've all grown, learned and risen together in our businesses. And it's in these moments that you realize that you're not just a chick with a dream.
You are a Phoenix rising from the ashes of corporate life. And if this is a journey you want to take. I would love to shorten that distance between day zero and year four. And it's totally possible.
So that year. I hit my old salary and then
Hold onto your hat My Good Woman. I started doubling my income every two to three years. Making more money than I had ever seen in my corporate life. More money than I expected to make more money than I ever thought I could make, because I was going into a profession that had never existed before. There were no comps.
And let me tell you. With doubling that income every two to three years, that view from the top, it's pretty stunning.
Act four. Entrepreneurship. Not for everyone. But maybe for you.
Okay. Again, we're being real here today. Not everyone is built to weather the storm of entrepreneurship. It is a rollercoaster ride where you are both the rider and the operator. But if you've got this gnawing feeling in your gut, that little voice whispering, you could do this. Then you've got to listen. If you don't, it'll keep you up at night. Wondering what if.
It will haunt you.
There's a social media version of the laptop lifestyle. Pictures of people sitting on a beach, kicking it with a cocktail and a computer while the money rolls in. And it exists to a degree but it is a trade-off. Even after seeing the income and the level of my client's rise and the volume of work rise. Running the business day to-day continues to present challenges. Sometimes cashflow is low and I scrambled to make it work. Sometimes I am blessedly flooded with tons of amazing opportunities. And I have to figure out how to serve a high volume of clients with a small team.
Or what to say no to and what to say yes to. And you might think those are high-class problems, but there is a lot nested underneath that problem. And, you know, from the other episodes of this podcast, that marketing and keeping the podcast consistent is a challenge.
And there is no such thing as work-life balance. It is a work-life tango.
I secured that game-changing connection to the management company when I was pregnant and only took two months off after a very difficult birth and postpartum depression because I was keeping the business going.
the ideal life. I had envisioned for myself, where I had lots of time for work and family. Was not materializing in the way I thought it would. Getting past the startup phase of the business seemed to be taking a lot longer than I had hoped or expected. And I was still often doing a great deal of the work myself.
And that's a tough place to be when you can see that what you have to offer is actually connecting with the market. People are paying you for what you're good at, and there is truly a business there. But you're always running two businesses. The one where you're serving people and the one where you're fixing and improving and growing the business that supports you, serving people.
And. you know, honestly, you guys, like if I had a chance to go back, I wish I would've had a coach every single step along the way. I'm not trying to be salesy in this moment because I am a coach for people that start and grow businesses. I'm saying it because It's a tough ride to be an entrepreneur.
Frank used to say, if I had a dollar for every time you told me you wanted to F it all and quit we would've made more money maybe than what you've made in your business Let's be real. I don't think that's true. But I wanted to quit a lot. in the 20 years I've had so far.
And most of the time I would not trade it for the world. the middle of this 20 year journey was full of difficult times nights when I couldn't sleep. Early mornings, hustling to figure out how to get more clients in the door. And constantly facing my own psychology and fears and imposter syndrome.
The peaks are higher in entrepreneurship and the valleys can be lower. But the highs do seem to last longer and plateau. And now I've developed the skills to bounce back from the lows I face plant plenty. But I recover more quickly and gracefully these days. That's the gift. One of the many gifts of more than 20 years in business.
But it is the reality of starting something and being the generator of that idea. You are always lovingly and sometimes stressfully connected to it and you never stop thinking about it. You will always be looking for ways to connect with and retain clients. You will always be watching your finances.
You will always be searching for great people to ride the coaster with you.
And you will always be looking for ways to make things smoother, easier better, more efficient. This is real entrepreneurship. And the best part. You can make your own choices. About when you work hard and when you step away. Who you choose to work with or not? The direction you'd like your company to move in. The creative avenues and partnerships you want to explore? How much fun you want to have. And how much money you want to generate.
As well as how to use it to fund the next level of growth and possibility.
And as your leadership skills, relationships and ability to serve clients grow. You can market effectively and successfully and set the price for working with the one and only you.
Owning this business has allowed me and my family to take amazing vacations. And shift schedules at a moment's notice. We've been able to help friends and family financially. And with our time. And live a lovely, worthwhile, fulfilling life. A life filled with possibility, love and adventure.
Act five. Well how about it? Are you ready for entrepreneurship?
So now that I've given you the unvarnished version of what it's really like to start and run your own business, what do you think. Because I'm not just here to entertain you with my tales of trials and triumphs. I've got something tangible for you.
If you've got that, you can't scare me vibe going you're in the right place. And if you're still not sure. Maybe. You're in the right place. Because I've got something to help you figure out if the CEO life is your destiny and it's time to put yourself to the test. See where this takes you next. And it's a quiz.
It's the, are you ready for entrepreneurship quiz? And it isn't one of those fluffy Time pass quizzes you take when you're avoiding work. Although I will say it is fun and a little goofy. But it is designed to help you take that leap of faith with just a bit more confidence.
And with a clearer idea of whether you are ready to say CEO or bust and mean it.
To take the quiz and take your next step go to DawnAndrews.com/BizQuiz. or grab the link in the show notes. I would love for you to be able to see what your next step is. And in the results, I give you clear directives about what you can do to move forward.
Well, my good woman. We've really written the rollercoaster today. Haven't we? So let's recap what we unpacked. The journey through entrepreneurship is not a walk in the park it's a Trek up a mountain, and sometimes the weather is not so friendly. But when you reach the peak and, or the peaks over and over again the view is absolutely worth it. There is nothing that will help you grow faster than engaging in running your own business. It will turn you into the person you were meant to become and help you fulfill your potential.
Starting your own business is challenging and there's a steep learning curve involved. But remember it is these very challenges that build resilience and pave the way for your future success.
It takes time to replace a steady income with the fluctuating earnings of a new business. And that's okay. Because Rome wasn't built in a day and neither is a successful business.
And most importantly, entrepreneurship isn't for everyone. But if there's a fire in your belly and you can't ignore the call to be your own boss. Then you owe it to yourself to explore that path. Do not stay in a job that has you feel unseen underappreciated, and passed over for progress.
Whew! You got me all fired up. I'm all ready for you to start your business.
So if you like this episode, Please hit that subscribe button on your favorite podcast platform and pass it on to another woman, you know, who might be really tired of her corporate job. And ready to jump out and get her own thing started. We've got plenty of exciting content on the horizon and subscribing ensures you won't miss a beat. Plus it helps other visionary women like you find My Good Woman.
So subscribe and join us on this journey to entrepreneurial greatness. And remember My Good Woman, this journey is all about betting on yourself and stepping into the unknown with courage and conviction.
Until next time.
You've got this. Thank you for joining me this week. To view the complete show notes and all the links mentioned in today's episode, visit mygoodwoman.com. And before you go, make sure you follow or subscribe to the podcast so you can receive fresh episodes when they drop. And if you're enjoying my Good Woman, leave us a review on Apple Podcast, reviews are one of the major ways that Apple ranks their pods.
So even though it takes only a few seconds, it really does make a difference and helps our show grow. This episode was produced by me and Julissa Ramirez. Thank you again for joining me, Dawn Andrews in this episode of My Good Woman.