How Documenting My Career Transition Accidentally Built a Gig Economy On-Ramp I Didn’t Know I Needed
I remember exactly when my heart dropped. Looking at the report, I saw my law practice revenue had fallen by 40%. I panicked. It wasn’t that I was failing as a lawyer—I was just overextended and too thin. For twenty-two years, I ran my own securities law practice. It felt steady until one night at 2 AM, with only my laptop’s glow and a mug of coffee, I finished the last lines of my screenplay. After an intense discussion about AI, what started as a hobby became an obsession. That script, called GOOD, slowly picked up awards. Over the holidays, I got swept up in creativity, writing two more scripts and letting that spark show up in every line.
And then my law practice revenue dropped 40%.
Not because I was bad at law. Because I was splitting the bandwidth. Clients could feel the distraction. I was choosing writing over taking on new work.
I had a choice: Abandon the writing and rebuild the practice, or go all-in on screenwriting (which pays nothing until it pays everything, and even then pays slowly).
Instead, I decided to document my experience. I saw it as a low-risk way to explore my career interests without giving up my law practice. This wasn’t a sudden jump—it was a careful test. I started by sharing the real, unfiltered process of my transition on Instagram (@monte99). I focused on the behind-the-scenes work: late nights, mistakes, numbers that didn’t add up, and the changes that did. For example, I found that my short, honest reels about balancing two careers did much better than static posts, bringing in more engagement and followers. These kinds of insights helped me turn my process into practical steps that others could use too.
I thought maybe 200 people would care.
Six months later, 1.3 million people—many going through their own career changes—care because they see their personal struggles and hopes in my story. My audience isn’t just a number. It’s a community of people facing the same challenge: balancing different careers and income streams while chasing what they really want to do.
And now something unexpected is happening: The documentation itself is becoming a revenue stream I didn’t plan for.
Brand partnership offers. Consulting requests. Speaking inquiries. Collaboration proposals.
The gig economy, I thought I was documenting? I'm accidentally building an on-ramp to it. It turns out that documentation can serve as a bridge between careers, enabling more seamless transitions by showcasing real-time processes and learnings. I've realized this journey can be distilled into a simple, transferable framework. Consider the three-step model: Document, Diagnose, Deploy. Document your process authentically, diagnose what works and what doesn't, and deploy refined strategies based on those insights. Here's what I'm learning in real time about how the freelance economy actually works and what it means when your career transition becomes an unexpected side hustle.
THE DOCUMENTATION THAT BECAME THE PRODUCT
I started posting because I was frustrated.
Frustrated that every “lawyer turned screenwriter” story is either:
Glossy bullshit about “taking the leap” (written by someone with family money)
Failure porn about inevitable flameout (written by someone too scared to try)
Nobody talks about the actual mechanics:
How are you explaining to a client that you’re less available because you’re rewriting Act 2?
What’s the conversation with your spouse when revenue drops 40%?
How do you decide which clients to fire when you need the money but can’t afford the time?
What does the Google Calendar actually look like when you’re running two careers simultaneously?
So I started showing it.
I didn’t perform or curate my posts—I just documented them. The response was huge: my unfiltered posts had an average 85% view-through rate. This shows how powerful it is to simply share the real process instead of trying to create a perfect story.
Screen recordings of my thoughts
Videos of 2 AM writing sessions
Photos of my color-coded calendar system
Voice-over explaining why I bought a $100/month grammar service (because just proofreading was costing me billable hours)
I posted as if I were submitting evidence. Because that’s what lawyers do.
WHAT HAPPENED (AND WHAT’S HAPPENING NOW)
First three weeks: 3,500 followers. Mostly friends.
In the first month, one of my reels got 50,000 views. It connected with people because it was relatable and had a clear appeal to action. The 30-second video gave a quick look into my life managing two careers, starting with a hook about the difficulty of balancing work. At the end, I asked viewers to tell their own stories in the comments, which really increased engagement.
Month 3: 300,000 followers.
Month 4: 700,000 followers.
Month 6: 1.3 million followers.
And then the DMs started:
“Can you consult on my career transition?”
“Would you speak in our webinar?”
“We’d love to partner on content about productivity tools.”
“Would you review our platform and share how you’d use it?”
I’m watching the gig economy materialize in my inbox.
Now I see that my audience is becoming the support I needed to fill the income gap. This change has shifted how I see myself—from just a lawyer and screenwriter to someone who helps others through career changes. As my audience becomes more than just numbers and turns into a real support system, I find myself growing into a community leader who values joint growth and learning.
THE GIG OFFERS I’M GETTING (AND WHAT THEY TEACH ABOUT THE FREELANCE ECONOMY)
Allow me show you what’s actually arriving. Because this is where theory meets reality.
Brand Partnership Inquiries
What they want: Sponsored content showing how I use their product in my dual-career workflow
Recent examples:
Productivity software companies (Notion, Calendly, etc.)
Legal practice management tools
Screenwriting software
Time-tracking apps
Professional development platforms
What they’re offering: $5,000-$15,000 per campaign for 3-5 pieces of content
What I’m learning:
Brands aren’t paying me just because I have 1.3 million followers. They’re paying for my confidence and credibility with a specific group of people.
My audience isn’t “everyone.” It’s:
Professionals attempting career transitions
Lawyers are burning out on traditional practice.
People are managing multiple income streams.
Mid-career folks who can’t afford to “just quit and follow their dreams.”
That specificity is valuable.
General influencers get paid for how many people they reach. Experts with a clear focus get paid for being relevant to the right audience.
Collaboration Proposals
What they want: Co-created content, courses, and workshops on managing multiple careers
Recent examples:
“Create a mini-course on productizing legal services.”
“Co-host a workshop series on time management for creative professionals.”
“Partner on a newsletter about sustainable career transitions”
What they’re offering: Revenue share, upfront fees, ongoing partnerships
What I’m learning:
The gig economy rewards demonstrated expertise over credentials.
I don’t have an MBA. I don’t have a coaching certification. I haven’t written a bestselling book about productivity.
But I have 1.3 million people watching me actually do the thing.
In the gig economy, showing real results matters more than making promises.
THE PATTERN I’M SEEING (AND WHAT IT MEANS)
Here’s what’s becoming clear as these offers arrive:
Pattern 1: The Transition Is the Product
I thought screenwriting was the product I was building. I was wrong. The real product is the system for making a career change without going broke. That’s what people want right now, while income from screenwriting is still far off. The bridge I’m building is more valuable in the short term than the end goal.
Pattern 2: Documentation Beats Aspiration
Every offer I get mentions something particular I shared: “I saw your reel about time management,” “Your post about the fund changed my approach,” or “The time-blocking system you showed actually works.” People aren’t reacting to my follower count—they care about the practical systems I share. The gig economy doesn’t reward vague inspiration. It rewards clear, useful methods that others can follow.
Pattern 3: Being specific lets you charge higher rates
A general webinar speaker might charge $150 an hour. But a small business attorney who became an award-winning screenwriter and kept earning through productized services and a documented system can charge $500 for 90 minutes. The more focused your expertise, the higher your rate. General skills are common, but specific skills are worth more.
Pattern 4: Multiple Small Streams Build Faster Than One Big One
I’m not getting one massive gig offer. I’m getting:
5-10 consulting requests per week
2-3 brand partnership inquiries per month
4-6 speaking opportunities per quarter
Ongoing collaboration discussions
On their own, none of these gigs replaces my law income. But together, they’re starting to make up for what I lost from my law practice.
Pattern 4: Multiple Small Streams Build Faster Than One Big One
I’m not getting one massive gig offer.
I’m getting:
5-10 consulting requests per week
2-3 brand partnership inquiries per month
4-6 speaking opportunities per quarter
Ongoing collaboration discussions
Individually, none replaces my law income.
Collectively, they’re starting to fill the gap left by the law practice.
Lesson 1: The gig economy values real results over fancy titles. Credentials matter less than showing your audience what you can actually do.
Lesson 2: When you share your personal struggles, you help people facing the same problems. Solving these issues not only supports them but also shows what people are willing to pay to fix them.
Lesson 3: Transitioning to gig work often accelerates faster growth than traditional career paths, creating unexpected safety nets that support bigger dreams.
Lesson 4: Don't see your audience as only numbers; view them as the infrastructure that supports and sustains your diversified income streams.
Lesson 5: Show your work instead of just talking about it. The gig economy values your real process and results, not empty promises.
THE DISTURBING TRUTH
I’m writing this article not because I’ve figured it out.
I’m writing it because I’m in the middle of figuring it out.
The gig offers are arriving. I’m accepting some, declining others, building systems to manage them.
But I don’t know yet if this works long-term.
I don’t know whether gig income stabilizes or depends on constant content production.
I don’t know if the audience grows, plateaus, or declines.
I don’t know if brands keep partnering or if the novelty wears off.
What I do know:
The gig economy is giving me an option I didn’t have six months ago.
The option to transition careers without panicking about the mortgage.
Not because one gig replaced my law income.
Because ten small gigs are filling the gap left by my reduced law practice.
THE BOTTOM LINE
I thought I was documenting my transition from lawyer to screenwriter.
I was actually building an on-ramp to the gig economy I didn’t know I needed.
And now I’m learning in real-time:
The freelance/gig economy isn’t about replacing your career with DoorDash.
It’s about creating enough different income streams so you can afford to go after the career you really want, even as your old job brings in less money.
For me, that’s emerging as:
Legal work (declining by design, productized, retained clients)
Screenwriting (growing slowly, long-tail revenue)
Gig work (brand partnerships, consulting, speaking—immediate, scalable)
None of those alone replaces a six-figure law practice.
Together, these income streams are helping me move toward the career I truly want.
Time is running out.
You can wait for the best moment to transition into a new career.
Or you can start documenting the imperfect process and discover that the documentation itself becomes infrastructure for the income gap you need to bridge.
I didn’t plan to build a gig economy safety net.
I just started showing my work.
And 1.3 million people decided that was worth following.
Not because it’s aspirational.
Because it’s real.
And in the gig economy, real is the sole competitive advantage that matters.
