More Than Meets the Eye

I’m starting off this blog with an obligatory “why-I’m-qualified-to-write-this” story. If you really want to skip to the good stuff, just keep scrolling until you see the list. 

For the lore freaks still reading, thank you and welcome. Let’s dive in.

I graduated college in 2018 bright-eyed, bushy-tailed, and eager to work. After having completed multiple internships (at super serious places like the Federal Reserve Bank), I networked myself into my first full-time job within three months of getting my diploma. 

After the honeymoon phase, I woke up and realized I was working up to 60 hour weeks for a fixed $42,000 per year. I was barely making $15/hour at my peak workload…after investing in a college degree. The illusion quickly faded. This was the reality I invested all that time and money into? 

As fate would have it, at the end of 2019, I led a successful in-house project that gave me just enough leverage to quit and position myself as a project manager for hire under temporary contracts. I had less than $5,000 in the bank and didn’t even know what a business plan was, but I trusted myself more than anything else in the world.

By 2020, I had become my own boss. I started working on various projects (mostly community initiatives) in higher education as a contractor, remotely, from my tiny third floor apartment in Philadelphia. I did it. I escaped! Or, at least I thought I did.

When I crunched the numbers after year one, I was looking at an ugly mess. It wasn’t actually working. There was no plan. I was losing money. I didn’t know how to price myself. My practices were shady (and sometimes dishonest). And to top it all off, I didn’t really like remote work. 

Despite doing the hard thing and finding the courage to leave my full-time job with benefits, I couldn’t quite figure out how to sustain myself as a solo entrepreneur with integrity.

After a cataclysmic project failure in 2023 that resulted in me getting let go by my top-paying client in Colorado, I was left stranded in the state unable to continue my business as it was. I was forced to make a choice: I either had to pivot, or quit this lifestyle.

The distant hum of the fluorescent cubicle lights tried to beckon me to return to the illusion of stability, but I couldn’t bring myself to face the corporate world again despite a total and complete obliteration of my career. 

After some deep intrapersonal work, I ended up building three new income streams from the rubble. Each one serves a unique purpose that aligns with my values: caretaking, teaching, and having fun. 

After five years of failing forward as an entrepreneur, I finally stand as a quasi-competent business owner with a unique mission and purpose that continues to grow and evolve. I have a long way to go and much more to learn. However, there are some major lessons I’d like to share and reflect on below, just in case it resonates with someone else out there doing the thing:

1. You don’t have to run your business like the rest of the world. Out the gate, I started doing business like a capitalist corporation since it was the only existing model I knew to follow. I copied successful movers and shakers. I pitched. I chased the bag. I was a LinkedIn loyalist. The deeper I got into “playing the game,” the more I realized I was perpetuating exploitation, profit over people, and the very behaviors and mindsets I was trying to escape from in corporate America. In year three, when my business flopped, I knew I had to start carving my own unique path that strayed from traditional business practices. For me, this looked like organic growth (even when it’s slow or messy) and always having multiple streams of income flowing simultaneously. Which brings me to the next lesson.

2. There are infinite ways to make money. As a new entrepreneur, it’s vital not to put all your eggs in one basket. The system taught us that the safest way to make an income was by pledging loyalty to a singular entity, idea, or pipeline. While focusing on a singular mission is important, I also learned that having multiple income streams is even more integral for growth, flexibility, and freedom. The ego loves to trick us into thinking we “should” do something complicated, serious, and socially “respectable” as a career, but you can make more money scooping cat shit than doing most office jobs. Open up. Money is fluid, not rigid. It adapts to your self-imposed limitations. 

3. You will fail often. Get used to it. I’d recommend not getting attached to your plans or your identity in your field. If what you’re doing is not working within a reasonable amount of time, don’t get caught in the sunk cost and “push through.” Instead, know when to cut the dead weight and move on. The first failure feels cataclysmic, I won’t lie, but it gets easier to stay calm in the chaos as you grow accustomed to handling the constant onslaught of change. Get comfortable losing—and losing with dignity—because it never ends.

4. NEVER negotiate your value. If you cost $100/hour, you cost $100/hour. Period. Not up for negotiation. If the client’s immediate instinct isn’t to make an investment in you after your pitch, move on. Your target market will be enthusiastic about spending their money on your service or product because what you offer solves their problem. Clients who haggle or resist your rates often don’t actually want you, they want to take advantage of you. Trust me, you don’t need the sale that badly. Let it go. There’s literally billions of other options.

5. Educate yourself about taxes. I almost shit myself when I saw a $7,500 tax bill after my first year in business. Americans, Uncle Sam demands upwards of 15% of your income (self-employment tax) if you’re on your own. Disappointing, but you can plan for it. Also—really hanging myself out to dry with this one—but you should know that tax deductions ≠ tax returns. When I started out, I thought I would be getting a tax return from all of the business expenses I had incurred in my first year. It does not work that way! Tax deductions mostly have the potential to lower your tax bill. It is very unlikely to get a tax return as a self-employed individual. Do your research.

Honestly, I learned a lot of these lessons the hard way, but the idea of staying trapped in a cubicle for the rest of my life seemed more terrifying to me than winging it with the potential of losing financial stability, so I took the leap. 

This lifestyle is not for everyone, but if even a teeny tiny slice of this resonates with you, I urge you to examine those thoughts and feelings. You don’t have to suffer in your work life and money doesn’t need to be complicated. However, walking a new path requires massive changes and sacrifice. Are you ready for that?