The Freedom Fantasy
Here’s what I thought when I was employed: “My boss is unreasonable. Deadlines are arbitrary. I don’t have control over my work. If I could just work for myself, I’d have freedom.” Here’s what I learned after years of client work: In a job you have one boss. With clients you have many bosses. And the problems I wanted to escape? Most of them followed me.What Actually Happens
Unreasonable Deadlines
In employment, your manager sets unrealistic deadlines based on business needs you might not fully understand. With clients, every client sets unrealistic deadlines based on their business needs you definitely don’t fully understand. And you have 3-5 of them doing this simultaneously. The difference: instead of negotiating with one manager you can learn to manage over time, you’re negotiating with multiple clients who all think they’re your only priority.Scope Creep
In employment, “just one more feature” from your PM. With clients, “just one more feature” from Client A, Client B, and Client C—all in the same week. And they’re all paying you, so saying no feels risky. The scope creep is multiplied by the number of clients. Each client’s “small ask” compounds into chaos.Meetings That Should Be Emails
In employment, 30-minute standup that should be a Slack update. With clients, each client wants their own check-in call. You spend 2 hours a day in “quick syncs” instead of building. You can’t skip these meetings—they’re paying you. Each client deserves attention. So now you’re in meetings all day across multiple projects.Lack of Context
In employment, you sometimes don’t understand why decisions are made. With clients, you definitely don’t understand their business context, their internal politics, or why they’re asking for what they’re asking for. At least in employment you can build context over time. With clients, especially short engagements, you’re always working with partial information.Not Feeling Valued
In employment, sometimes you feel like a cog in a machine. With clients, you’re definitely a vendor. You’re brought in for specific tasks. You’re external. And you’re the first to go when budgets get cut. In employment you at least have the possibility of becoming integral to the team. With clients, you’re always somewhat disposable.The Problems That Actually Are Better
To be fair, some things do improve: You can fire bad clients. Eventually. When you’re not desperate for money. You can raise your rates between projects. You can charge different clients different amounts. You can say no to projects that don’t fit—when you have enough work. You can work from anywhere—but client meetings still happen, and if you have clients across time zones, you might be taking calls at 6 AM and 9 PM. The catch for all of these: only when you have enough work. When you’re desperate, you say yes to everything.The Hidden Problems
Beyond the obvious stuff, here are the problems I didn’t see coming:Decision Fatigue Multiplied
In employment, one set of priorities, one codebase to learn, one set of tools and processes, one company culture to navigate. With multiple clients, different priorities for each, different codebases and tech stacks, different tools and processes for everything, different communication styles and expectations. By Wednesday you’ve made more decisions than you used to make in a month. You’re exhausted, and you haven’t even built anything yet.Context Switching Is Brutal
Monday morning: 9 AM Client A (React, e-commerce), 11 AM Client B (Python, data pipeline), 2 PM Client C (Vue, internal tools), 4 PM back to Client A. Each switch requires loading different codebases into your head, remembering where you left off, switching communication styles, changing what “good” looks like for this client. You spend more time switching contexts than actually being productive in any single context.You’re Always “On”
In employment, work hours are defined, you can mostly disconnect outside them, vacation is actually vacation, sick days are a thing. With clients, each client expects availability. You can’t ignore Client B’s urgent message just because it’s your weekend. Vacation means hoping nothing breaks. Sick days mean falling behind with everyone. The boundaries you wanted from leaving employment completely disappear. You’re more “on” than you ever were.The Gap Anxiety
In employment, job is secure (mostly), paycheck is predictable, you can plan months or years ahead. With clients, every project ends. What happens after this? Constantly thinking about the next client. Can’t fully relax into the current work. Even when you have work, you’re worried about not having work. The anxiety never fully goes away.The Types of Clients
After years of client work, most clients fall into a few categories: The Dream Client (rare): clear about what they want, respects your expertise, pays on time, reasonable about deadlines, good at communication. Do great work, maintain the relationship forever. The Indecisive Client (common): “I’ll know it when I see it,” changes requirements constantly, can’t make decisions, wants you to read their mind. Over-communicate, document everything, charge for revisions. The Micromanager (exhausting): wants daily updates, questions every decision, doesn’t trust your expertise, hired you but won’t let you do the job. Consider not renewing. The Disappearing Client (frustrating): hires you urgently, then vanishes, doesn’t respond to questions, reappears at the deadline angry you didn’t finish. Document all communication. The Budget Client (often not worth it): wants cheap work, questions every hour, asks for discounts constantly. These clients rarely become less difficult. The Unicorn Client (treasure these): becomes a long-term relationship, trusts you completely, pays well and on time, refers other clients. Prioritize them.What Makes Client Work Harder Than Employment
A boss is one relationship you can invest in learning over time. Clients are multiple relationships, each different, constantly churning. You’re always adapting to new people, new expectations, new communication styles—while also doing the actual work. You’re always selling. Selling to new clients. Selling scope changes. Selling timeline extensions. Selling rate increases. Selling renewals. You handle all the business stuff. Sales, marketing, accounting, legal, IT. Every hour spent on business operations is an hour not billed. The emotional labor. You can’t show weakness. You’re always “on.” Even when you’re struggling, you have to appear confident and capable. No safety net. Bad week? You don’t bill. Sick? You fall behind. Client cancels? Income disappears immediately.When Client Work Actually Makes Sense
Despite all this, client work can be the right choice if: You have multiple clients—never depend on one client for more than 50% of income. You charge enough—2-3x what you’d make employed (hourly). You can say no—only when you have enough work to turn down bad fits. You enjoy variety—if context switching energizes you instead of draining you. You’re good at sales. It’s a bridge, not a destination—great as a step between employment and products. But as a permanent model? For most people, it’s exhausting.My Experience
I’ve done client work in various forms for years. What I liked: higher income than employment, variety of problems, some flexibility, could work remotely. What I hated: constant context switching drained me, relationships with clients felt transactional, always selling, gap anxiety was exhausting, missed colleagues and domain depth. What I’m doing now: moving toward a portfolio approach. Some employment (stability, colleagues, depth), some products (ownership, upside), maybe some consulting (variety, high rates). But pure client work as my main income? I’m done with that.Questions to Ask Before You Make the Jump
Thinking about leaving employment for client work? About selling: Do I enjoy selling or dread it? Can I handle rejection repeatedly? Do I have a network that could become clients? About money: Do I have 6-12 months of runway? Can I handle irregular income? What’s my actual burn rate? How much do I need to charge? About isolation: Do I work well alone or need colleagues? Where will I get professional feedback? About work style: Does context switching energize or drain me? Do I prefer depth or breadth? Can I handle multiple relationships simultaneously? Am I good at setting boundaries? About reality: What am I actually running from? Will those problems follow me to client work? Am I being realistic about the tradeoffs?The Path I Didn’t Expect
At 37, after years of client work, I’m interviewing for employment again. Some people might see this as going backwards. I see it as learning what I actually value: colleagues over isolation, depth over breadth, stability over maximum income, clear boundaries over “freedom.” That doesn’t mean client work was a mistake. It taught me how to sell, how to manage relationships, what I actually value in work, what kind of problems I want to solve. Now I can make an informed choice instead of running from something.The Truth About Freedom
Here’s what nobody tells you: trading one boss for many isn’t freedom. It’s just more bosses. Real freedom might actually be: choosing employment with good boundaries, building products on the side, having financial stability so you can say no, working with people you respect. Freedom isn’t about who signs your paycheck. It’s about having options and making intentional choices.Trading one boss for many isn’t freedom—it’s just more bosses with more complexity. Understand the tradeoffs before you jump. And remember: choosing employment after freelancing isn’t failing. It’s growing up.