Episode 100. Burnt Out Side Hustler to Multiple 6 Figure Coach (Part 1): The Mistakes & Challenges

If you notice, this is Episode 100. ONE HUNDRED. That’s all I wanted to say. Super anticlimactic start to this episode.

For Episode 100, I want to dive deeper into how I went from being a burnt out side hustler who ended up quitting my business for seven months, back in 2019, to now taking my business to multiple six figures and I am now full time in my business. This will be a two-part series on the podcast.

Specifically, in this episode, I want to share three key obstacles that came up in my journey since I started my business. They either kept me stuck or slowed me down.

And in the next episode, Episode 101. Burnt Out Side Hustler to Multiple 6 Figure Coach (Part 2): The Biggest Lessons & Shifts, we will look at three of the most profound lessons that have helped me see massive shifts and results once I really learned and implemented those lessons. These are the biggest needle movers in my business.

I hope that by sharing my own honest journey with all the ups and downs, we’re able to recognize that when challenges do come up for when things don’t go our way, we’re able to discern that it’s not a problem. And it’s not because you’re doing something wrong or that you’re not cut out for this.

But rather, we’re able to identify that this is a natural part of the entrepreneurial journey. And even though everyone’s journey will look different, I do believe there are nuggets in my own experiences that you can take away.

We will all go through our own challenges and lessons, and my hope is that we can all learn from one another. 

As usual, if anything we talk about in this series resonates with you and it’s how you want to take your brand and business to the next level, I’d love to invite you to join us inside  the Thought Leader Club 1:1 + Community Program focused on helping you build a body of work that not only lets you become known for something but also magnetizes clients and opportunities to you.

For all of the details, head on over to cheryltheory.com/program to send in your application. I cannot wait to see you on the inside.

In This Episode:

• Feeling not good enough led to my burn out
• Feeling not good enough also led me to spend too much time looking at what others were doing
• Shiny Object Syndrome led to doing tasks that distracted me and took time away from honing my craft
• Entrepreneurship may not be easy, but I know you’re going to figure it out and move forward from it

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Feeling not good enough led to my burn out

Let’s start with something that I think many of us experience in some way, shape or form.

For anyone who has already started your business or you’ve been contemplating it, you likely have already seen how business can trigger you and bring up all your fears and doubts.

A lot of these thoughts and feelings that come up are extremely layered. It’s not as surface level as we think. 

For example, if you experience resistance towards selling, it’s not because you’re just too introverted or not charismatic enough to show up online.

Rather, it could be because throughout your life, you’ve seen examples of sales people that really rubbed you the wrong way. Or, if you feel resistance towards not seeing results fast enough, or you’re feeling frustrated with the process.

It’s not because you’re not doing something right.

It could be because you’re someone who’s used to hitting your goals, or you’re used to being the underdog where your hard work always resulted in hitting your goals, but that’s not happening in your business and now your ego feels really bruised.

Or it could be for a lot of different reasons. But it is definitely layered and multidimensional. 

For me, I could see that a root cause of my burnout back in 2019 was because I deeply felt like I wasn’t good enough or talented enough. I felt that I needed to do more in order to at least make it seem like I am good enough.

I shared a concept called feeling like an average high achiever back on Episode 92: Building a Business Even if You Feel Average. In a nutshell, how I define this is feeling like you’re good at what you do, but you’re not the best, and as a result, the recognition you get is just kinda so-so. You feel like people do know that you’re good at what you do, but that’s about it.

The credit and recognition always go to the small percentage of people who are seen as the best and hence are better than you in whatever it is that you’re comparing yourself to.

How this translated into a major block in my own business was that in the first 5 months of my business, it felt really hard. Yes, I signed clients and I created “results” within the first month of starting my business, but this period of time felt really, really hard.

I hustled hard from March till August 2019. And by August 2019, I basically crashed and burned down my business. I literally shut everything down and stopped my business for the next 7 months. 

I think for many of us, in the context of our business, feeling like we’re not good enough is so prevalent. I think it’s especially prevalent for those of us who have the drive and work ethic, and we also identify as someone who is high achieving or capable of achieving big things.

But we feel like we’re not as good as other coaches or entrepreneurs, maybe because they’re way more established or are making way more money or are super well known in their space and are now speakers and authors.

We feel like we have to compensate by working really hard, by doing more, and by doing better so we can also be recognized for the value we bring to our industry and become an in-demand coach or entrepreneur. 

I was navigating so much internal self doubt and comparisons during the first 5 months of my business. I really believed that I had to work my utmost hardest to “make it” as a coach.

I really felt that I had to do 20 different things at once and go for quantity because I thought that is what’s going to help me create success, and that I could just work hard my way to success.

So, for those five-ish months, on top of my full time job as a research assistant, I also worked with 1:1 clients, posted on IG stories every day, posted several times on my Instagram feed every week, had a private Facebook group where I did weekly and month challenges and live streams, sent out weekly email newsletters, participated in other people’s Facebook groups, posted on LinkedIn, started a podcast, and even posted a few YouTube videos.

That’s a lot of work, especially for a side hustler. Long story short, I burned out. Fast. I shutdown my business for 7 months entirely.

It took 7 months for me to not only rest, but also to heal my relationship with myself. I was committed to rebuilding my business, but I knew I had to re-examine my views on what it means to be a successful entrepreneur, my views on hard work, and my views of myself as someone who has a lot to offer. Rather than seeing myself as lacking and hence overwork to compensate.

This is the uncomfortable work of entrepreneurship.

You can choose not to do the identity work, and only do the strategy. For me, when I only did the strategy, I hated who I was and the process and it was simply not sustainable.

I know for a lot of you listening to this, you don’t want to disappoint others.

For example, a lot of us want our parents to be proud of us because they worked so hard. For me, my parents immigrated to the United States and I grew up in North America. And I wouldn’t have been able to have the upbringing and resources I had access to if it was not for the sacrifices and hard work they put in.

So growing up, I internalized this feeling of “I have to work hard not just to be good enough, but also to give back to my parents who had given me so much.”

I felt like I have to have it all together and that I can’t share that I’m struggling, because I don’t want to burden others. 

How this could look in our business is that you might also see yourself pushing off things that you actually need to sustain you. Or maybe you’re avoiding uncomfortable things like exercising, seeking support and simplifying your business plan, because you don’t want to fail or seem like you don’t have it together. A lot of your decisions are probably stemming from the feeling of needing to make it all work.

And as a result, you’re putting a lot on your shoulders. You have this budding business that you really, really care about, but you also have other things on your plate such as work, family, relationships, and other things.

So it makes sense why you’re questioning your capability as an entrepreneur, why you have so much expectations of yourself, and so on. It’s because you truly do have a lot on your shoulders, right?

Here’s what I want to say to anyone who can relate to any of this.

First, you are resilient as an entrepreneur and as a human being, and you will figure it out. Challenges, frustrations and self doubt are inevitable. It’s required in the journey as an entrepreneur.

Second, your identity is not defined by your past. You get to define your identity, who you are, and what you want to create. You are very capable, intelligent, hardworking, and brilliant.

You are completely capable of creating your own dream business and career, even if it’s unconventional or not exactly the one others, such as your parents or friends, expect of you. 

And if building a highly impactful and profitable business is what you feel strongly called to do, please continue to stay grounded in that vision and dream.

Because being able to stay rooted to your beliefs, dreams and vision is a skill in entrepreneurship.

You have this vision for a reason. I would even venture to say that it is part of your identity. This is who you are.

In order to move forward in your business journey, being open to gaining deeper awareness into the multilayered parts of your identity is a required part of the process. Because you can’t outwork your self doubts and lack of belief in yourself.

You can’t hustle your way to success. You can get to a certain level, but it can only get you so far if the foundation you’re building on is shaky.

Your identity is the core of who you are, literally. Your belief in yourself is going to matter, and identity work can look different for anyone.

I encourage all of us to explore what exploring our identity could look like for each of us.

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Feeling not good enough also led me to spend too much time looking at what others were doing

Besides overworking myself because I felt like I wasn’t good enough and therefore I felt like I needed to compensate by doing as much as possible. My lack of confidence in myself, especially at the beginning of my business, also led me to compare myself a lot with others. Especially with other business coaches. 

What ended up happening was that I spent so much time paying attention to what other business coaches were doing, whether it be coaches who were way more established or coaches who were seemingly at the same level as me.

I paid so much attention and kept tabs on them. This left me feeling resentful, jealous and judgmental of others. It also made me doubt my own ideas and voice.

So much so that because I was up to my eyeballs consuming so much from others, I felt like my own ideas were not good. I actually ended up producing and posting content that honestly sounded like a lot of people I was following or creeping on. Whether it be the language or the topics of the content, you couldn’t tell me apart from other business coaches.

I didn’t quite realize that I was unknowing modeling after others and basically looking and sounding like everyone else until a very peculiar phenomenon started happening.

I would book sales calls for my coaching program, but interestingly, everyone was saying “Oh I’m actually going to do more discovery calls so I’ll let you know” and that’s when I realized damn. Who am I?

But that was exactly the wake up call I needed to start really using my own brain. It challenged me to think bigger and develop more self trust in my own ideas.

It pushed me to be more creative and more bold. I actually started asking myself. What are my ideas? What do I want to say? That’s why in 2021, I started to become known as the soft launch queen. Because I started to reverse engineer my own process and identify the unique skills or approach I bring to the business coaching industry.

This is why I strongly believe that 2021 was a six-figure year for us. Because I had this realization very early in 2021, I was able to go out of my comfort zone for the rest of the year and really build brand awareness for what I want to be known for.

I unpacked how I want to teach my signature skill of soft launching and paid extra close attention to how to better teach our clients this skill of soft launching. How to create even more specific, bold, and unique messaging for my coaching offers and also content that deeply resonates with our community.

It was definitely a punch to my stomach when I realized, wow, I’ve been creeping on others so much, so much so that I literally lost time and money as a result. Like really think about how that could be true. The more we spend looking at what others are doing and taking notes on them, the more time and money we miss out on. Really let that sink in.

Here’s the main point I want to emphasize in hopes that it can help all of us. First, we all have our unique thought leadership because we all have our own opinions, ideas, lived experiences, values, story, and so on.

Second, having an opinion about your industry is what will make you stand out and really showcase your expertise at a much higher level. I’d also argue that when you share your opinions, the most important thing it does is that it demonstrates your values. And guess what? Our clients are looking for coaches who share the same values as themselves.

That’s why inside our program The Side Hustle Club, we help our clients first identify and hone in on what their own unique thought leadership, and how it ties in with their offer. Then, we work on their delivery and being able to communicate their thought leadership in a powerful and compelling way.

This is what differentiates you in your niche or industry. When you’re known for your own unique thought leadership, competition isn’t even a concern anymore because you know what’s unique about you and what you bring to the table.

I had to believe in the power of my own voice, my story, my experiences, and my skills first. Only then could I create my first $10k month, then my first six-figure year, and then go from side hustler to now a full time coach with a multiple six-figure business. That’s why this is such a big component of my work with our clients.

To anyone listening to this, I really mean it when I say that your thought leadership matters. We all have it, especially if you’ve felt like your own ideas or experiences or achievements aren’t good enough because society and culture prized other ones over yours.

Because you’ve grappled with your own confidence in your voice, let that be a sign that your voice is needed. If you’ve felt like your own ideas weren’t good enough, that’s just because society or school or the workplace conditioned us to believe that only certain molds of ideas are good enough and worthy of being recognized. That is not true.

We all have thought leadership and your thought leadership is what will set you apart in your niche or industry. It’s what will help you truly build a sharp and uniquely differentiated brand. 

It’s what will help clients see that you are the coach for them and hence drives them to apply to your program. Your voice and ideas need to be seen and heard. I’m dead serious here. 

To help you start marinating on what’s your unique thought leadership, here are three question to ask yourself: 

1. Are there convention advice, approaches, or viewpoints in your industry that you disagree with? What are opinions you hold about your industry that you’re nervous to share because you’re worried it will ruffle feathers, but is a viewpoint that you deeply believe in? 

2. What do you care about so much? Why is it important to you to do what you do in your business? Why do you believe that what you do can profoundly change someone’s life? 

3. What’s something you changed your mind about? For example, maybe you used to believe in XXX but after some personal experiences you’ve now come to believe YYY instead? And why is YYY better for your people and community?

If you’re able to answer these questions and learn to communicate that in your content and marketing, that’s how you build a uniquely differentiated brand because these are all opinions you and your community hold.

It stems from you and your own lived experiences, as well as the collective ones of your people. And building a lifelong, highly impactful business and brand will require you to know how to communicate the above. 

This is how you build connections with your ideal clients. This is how you showcase your own values and attract clients who share the same values as you. This is how you show, not just tell, your expertise and “authority” in your niche. All of this is part of the work we do inside The Side Hustle Club program. 

Your story, message, and work deserves to take up space through your content online, in your containers with clients, and also in other rooms and stages globally. Your work matters. Your story matters. Your voice matters. The impact you make matters. And when we impact and help others, we get paid.

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Shiny Object Syndrome led to doing tasks that distracted me and took time away from honing my craft

There are often times when there’s an itch we want to scratch in our business. Maybe it’s launching a webinar or starting a YouTube channel or launching a new offer.

While I’m not saying not to do those things, because I think that would create a highly restrictive business, I also recognize that there are often times in the business when you’d want to choose to focus on improving what you’ve started on, rather than starting from complete scratch with something new every few months or so.

Let me share my personal experience with this. In 2021, I practiced launching small group programs. I launched four separate cohorts of the group program starting from the beginning of 2021 and my last one was around early 2022. 2 people → 4 people → 6 people → 7 people.

As you can see, we had more clients join us each time. For each launch, I did my signature “soft launch” style and each time, I would evaluate my strengths and areas for improvement from the previous launch so I know what I’d like to do for the current launch.

And as a result, I was able to observe both the mindset and strategy changes I wanted to refine. I didn’t change my offer or business model. I didn’t change my strategy. Because I kept soft launching and selling my offers simply on Instagram and on the Side Hustle Club podcast.

But rather, I would launch again, doing the same action items, but do the action items with even more energy, potency and impact each time around.

For instance, I experimented with new ways of talking about my offers. This is a great example of how focusing on practicing skills, and here it was the skill of soft launching for a small group program, can reap benefits over a relatively short amount of time. Because in a twelve month time span, we invited 2 + 4 + 6 + 7 = 19 amazing clients into our group program.

Now, I want to share where I totally did not take my own advice and instead, sold a $97 ebook and $197 workshop, both during 2021. I honestly did this out of FOMO (fear of missing out), it was like an itch I really wanted to scratch. And that’s not a problem whatsoever, because I had so much fun creating both offers.

However, here’s the lesson: Because I only did each of these once (i.e. 2 weeks for each product), and I never repeated selling them ever again or offering them again, I wasn’t able to work on improving the skill of selling either offer or even in the delivery of either offer.

Looking back, I created new offers because I wanted to diversify my product suite. I got FOMO when I looked at other coaches, and I was getting bored of selling 1:1 so I kept launching small group programs.

Although I know that if I had simply continued selling coaching (1:1 or group), I probably could have made more money in 2021 and I would have been able to better my coaching skills, which would then allow me to create a strong standalone digital offer. But I wouldn’t have been able to learn this lesson otherwise.

Overall, I was able to evaluate each group program launch and pick up on things I did well and things I’d do differently next time → Each launch got bigger and better.

However, I cannot say the same for the digital products. The lesson here is that selling and launching is also a skill I need to practice and repeat!

So how does this apply to you?

I’d summarize it into two parts:

First, if you aren’t confident on the “basics” (for example, booking sales call for your 1:1 program), it may be even more difficult to make something new/different/more advanced actually work (ex: Selling a group program, where you need to get multiple individuals to book a call and say yes on the call).

Second, it’s also harder to see improvements when you’re working on 5-10 (or more) skills at once. It’s easier to get overwhelmed and discouraged when there’s so much to work on simultaneously.

Mastering the bare minimum number of skills can honestly lead to your first $5k month, $10k month, and even six-figure year.

If anything, the skills that you’re going to work on at the earlier stages of your business are going to be needed even at the six-figure level. For example, you still need to do marketing, sales, and help clients get results at literally all levels of your business. You cannot skip these skills.

Doing the bare minimum, works. But more often than not, early-stage coaches get impatient and bored from doing the basics and making small improvements, over and over again. 

That’s why I suggest staying focused on letting these small 0.001% progress compound into bigger wins.

Here’s a practical tip I want to offer: Learn to get really really good at selling only one offer for at least 6 months or 12 months. 

The reason is simple: You need time to understand your strengths in selling, the areas you want to improve on, and how to address questions or objections that your audience has about working with you.

Changing your offer isn’t going to change or improve your marketing and sales skills. It also takes time to understand how you want to help people.

But if you keep changing your offers, it’s harder for you to gain clarity on what you’re good at or what refinements you need to make in your offer.

Perhaps even more importantly, it also takes time to build brand awareness and demand for one offer alone.

But if you keep flip-flopping around offers and continue to create a new one, it’s a lot harder to build up the reputation for one signature offer.

All that to say, it’s not that I’m saying NEVER create a new offer or restrict yourself if there’s something you really really want to do. Rather, I would suggest that if there’s something new you want to try, try it first.

Second and more important, give yourself a longer time line to try it out. Meaning, give yourself at least 6 or even 12 months to practice it and get really good at it.

Every new thing in your business is essentially a new skill set, and skills take time. It takes practice to get good at a skill and to see results from that skill.

So, don’t just try it once and think it’s not working if you aren’t immediately seeing results. Keep refining your skill with time and practice, rather than continue to jump from strategy to strategy.

Every strategy is simply a skill. And the best part about skills is that it’s not like you’re either good at it or you’re not. Skills can be honed and improved on.

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Entrepreneurship may not be easy, but I know you’re going to figure it out and move forward from it

Those are three of the mistakes, failures, or challenges that I’ve experienced in my years as an entrepreneur. These are ones that have definitely held me back in noticeable ways, so I felt extremely called to share them with you in hopes that you can take away some nuggets that are helpful to you and your business.

Whatever challenges you might face in your business journey, I know that you’re going to figure it out and move forward from it. Entrepreneurship may not be easy, but I know that the work you do as a coach or entrepreneur matters to you.

This concludes Episode 100, thank you so much for tuning in and I cannot wait for the next episode, Episode 101: Burnt Out Side Hustler to Multiple 6 Figure Coach (Part 2): The Biggest Lessons & Shifts, where we will shed some light on some of the biggest needle movers in my business.

Lastly, if anything we talk about in this series resonates with you and it’s how you want to take your brand and business to the next level, I’d love to invite you to join us inside the Thought Leader Club 1:1 + Community Program focused on helping you build a body of work that not only lets you become known for something but also magnetizes clients and opportunities to you.

For all of the details, head on over to cheryltheory.com/program to send in your application. I cannot wait to see you on the inside.

Sounds good? Awesome. Let’s get to work.

Listen to the Episode