Dear Diary: My Hardest Lessons in Entrepreneurship
Written by Allison Santana 3/16/2025Hello, Gentle Reader,
If you’ve made it to my "Diary," thank you. Truly.
I named my website and social media platforms Switching Lanes Diary because I thought I was going the blogging route at one point. I truly despised the word ‘blog’. I thought ‘diary’ sounded cooler. And I liked Switching Lanes, because it empowered me to own my many pivots in life.
So, there’s that (whether or not you were wondering)!
This entry is a little different from my usual content, but today, I just want to share my heart. If you're here, chances are you’re navigating a season of uncertainty, just like I was. And if that’s the case, let me be the first to tell you—you can do this. You should do this. And honestly? You’ll probably be better at it than me.
A couple of years ago, I moved to a new state with my four kids, determined to carve out a better future for us. But reality hit hard. My cleaning business wasn’t taking off, and finding a stable job felt impossible. I pivoted again and again—podcasting, insurance sales, even driving for Amazon—trying to find something that fit, something that gave me both financial security and a sense of purpose. But no matter what I tried, I felt like my dream life was slipping further and further away. I knew that if I didn’t make a bold move soon, I’d wake up one day trapped in a life I never wanted.
Then, like so many others, I found myself doom-scrolling on TikTok. And suddenly, I saw it—creators making insane money online, building real businesses right from their phones. I had always dismissed TikTok (probably because of all the choreographed dances—I can’t dance to save my life), but something clicked. These weren’t just influencers; they were digital marketers, course creators, and business owners leveraging the platform in ways I had never considered.
I kept seeing one opportunity pop up over and over: digital marketing. People were reselling courses that taught actual skills, others were selling digital products, and some were making full-time incomes doing both. Then, I came across a couple who had gone from teacher salaries to making multiple six figures in less than a year. That caught my attention. Sure, they had a massive following, but what intrigued me most was their business model—selling done-for-you courses that allowed them to keep nearly 100% of the profits.
That part? That part made sense to me.
With my background in podcasting, teaching, and even helping create online workshops, I knew I could make this work. It felt like the beginner-friendly approach I needed. But even though everything seemed to line up, I still sat on the decision for another month. Why? Because my confidence was shot.
I kept second-guessing myself. What if I failed again? What if people rolled their eyes at me starting another business? What if I just wasn’t cut out for this?
It still took me another month to make the leap. Honestly? My confidence was wrecked. I kept beating myself up for not having my life figured out. The thought of presenting yet another business venture to the people in my life filled me with dread. What if I failed? What if they rolled their eyes? What if I just wasn’t good enough?
In times like these, I turn to the voices that pull me out of my own head—and Mel Robbins? She’s one of the best at it. Her podcast hit me with a reality check I desperately needed: most of the fears I had about starting over weren’t even real. I was inflating them in my mind, giving them way more power than they deserved.
And let’s be real—people don’t care as much as we think they do. They might judge, they might have opinions, but at the end of the day? It’s like a fart in the wind. (Yep, I said it.) They react, wrinkle their noses for a moment, and then move on to the next thing to criticize, complain about, or gossip over.
That realization was freeing.
Starting over wasn’t some red flag or personal failure. It was just life. And given everything I had been through in the last few years, the fact that I was still standing—still pushing forward—was proof that I wasn’t lost. I was learning. I was adapting. But if I wanted this next chapter to be different, I had to step into it with a plan.
Then came another fear, one I almost felt guilty for having: Would people take me seriously?
I know how that sounds. Maybe I’m supposed to pretend I’m above it, but let’s be real—I’m a plus-size woman in my mid-30s, with acne and dark circles from sleep apnea. Social media is full of polished, picture-perfect “boss babes” with flawless skin, high-energy aesthetics, and designer everything. Would people trust me as an authority in anything?
We all know social media isn’t real—at least, not entirely. But our brains still believe what we see first. So I couldn’t help but wonder: could I, looking the way I do, genuinely inspire someone to take action? Could I make them believe in me enough to believe in themselves?
After many empowering episodes of Mel Robbins’ podcast and a heart-to-heart with the people who matter most—my kids—I knew it was time. Time to take a bold leap, to bet on myself, and to build the incredible life I knew we deserved. After all, how could I teach my children about courage, resilience, and chasing their dreams if I wasn’t willing to lead by example? Kids don’t learn from what we say—they learn from what we do.
So, on Christmas Day, sick in bed with the flu and exhausted from my grueling Amazon delivery job, I made a decision that changed everything. I ordered Digital Wealth Academy—the course that would teach me digital marketing and allow me to resell it. That same day, I committed to posting on social media consistently. To my surprise, I actually enjoyed it. I even pushed myself to go live—terrifying, but absolutely worth it. And just like that, my journey as a content creator and digital marketer began.
For the first time in a long time, I wasn’t just trying different things—I was actually thriving. I tapped into my creativity in ways I hadn’t in years, applying everything I learned from the course and pushing myself beyond my comfort zone. And more importantly, I gave myself permission to start messy, to be a beginner, to improve as I went. Like Doechii said, “…I have the right to be bad when I start when I first start...”
And here’s what I’ve learned: nobody is coming to save you. No matter how many setbacks or struggles you’ve faced, you are the hero of your own story. You are the only one who can decide what happens next. Make a plan, execute it relentlessly, and be willing to adapt along the way. You have the right to take up space, to claim your seat at the table—or better yet, to build the damn table yourself.
So now, I ask you: what’s the leap you’ve been afraid to take? What’s the thing you know could change your life, but fear, doubt, or judgment is holding you back? Because if you take one thing from my journey, let it be this: you don’t have to be perfect to start—you just have to start!
XO -Allison
P.S. I totally got fired from that job like a week later, so good thing I got out of my own way. 😅