These days, I see quite a few clients who simply want to work for themselves. They’re not trying to build empires with layers of staff and multiple departments. Most just want to be freelancers, maybe bring in a subcontractor or two when needed, and enjoy more control over their time, income, and lives.
Honestly, I get it—I’m in the same boat. These days, I consider myself self-employed: no payroll to run, no office politics to navigate. Just me, a few part-time subcontractors, my work, and the people I help. That’s why I thought it was time to set the stage for what lies ahead when you choose this path. What follows is shaped by what I’ve learned firsthand over the years and by the patterns I’ve seen in the clients I advise, especially in areas where they tend to encounter difficulties or surprises.
Are You Wired for This?
Let’s start with a hard truth: not everyone is cut out to be self-employed. It’s not about intelligence or ambition. It’s about wiring. Self-employment demands a certain kind of resilience—the ability to wake up every day and push forward without a boss looking over your shoulder. You need a healthy tolerance for risk, a strong sense of internal drive, and the ability to handle the emotional ups and downs without losing focus.
It’s a constant balance between believing in yourself and questioning everything you’re doing. You’ll second-guess your decisions. You’ll feel imposter syndrome. You’ll doubt whether the income will ever stabilize. I’m here to tell you that it’s normal. But if you have a high degree of self-motivation, a bias toward action, and a willingness to learn as you go, you’ll more than likely be okay.
Rewiring Your Thinking
Making the leap from employee to self-employed requires more than a new business card—it’s a full mindset shift. In a job, you wait for instructions. When you’re self-employed, you write your own to-do list every day. In a job, there’s a structure someone else built. Here, you’re building the structure while trying to operate inside it. If I’m honest, it can be pretty exhausting at first.
Discipline becomes your best friend. You’ll need to create routines that support your productivity—and stick to them, even when no one’s watching. But the good news is that you get to shape your days. You can lean into your energy patterns, create work that aligns with your values, and ditch the stuff that never made sense in the first place.
Setting Up Shop—Literally
I can’t tell you how many people underestimate the value of a proper workspace. Whether it’s a home office, a spare bedroom, or a table at the local co-working space, you need a dedicated environment that signals to your brain: “This is where work happens.”
My own office is set up in what used to be a bedroom. It’s fully dedicated now, though I did keep a Murphy bed tucked into one side of the closet—just in case. The rest of the closet has been converted into shelving for office supplies. One entire wall features a built-in bookcase filled with my favorite business books and a few awards that remind me why I do this work. I work from a large L-shaped desk with a matching file cabinet that keeps my records organized. My main setup includes a desktop PC with three large monitors arranged in a semicircle for maximum efficiency and an all-in-one fax/copier/printer. I also keep a laptop handy for when I’m on the go.
Because I create video content and meet with clients via Zoom, I’ve added a green screen drape that attaches to the ceiling with magnets, along with studio lights and a 4K webcam to give a polished, professional look.
If you don’t have a dedicated room and plan to use your dining room or kitchen table, I’ll be honest—you’ll probably struggle to get into the zone. Your environment matters more than you think.
Taming the Clock
Time is your most precious currency when you’re self-employed. The challenge isn’t just doing the work; it’s deciding what work is worth doing. You’ll quickly discover the difference between being busy and being effective.
One of the best habits you can develop early on is scheduling your priorities instead of prioritizing your schedule. Block time for client work, yes—but also make space for marketing, networking, and learning. Otherwise, your business may run, but it won’t grow.
And don’t forget to set boundaries. Just because you can work anytime doesn’t mean you should. That said, I genuinely enjoy being the master of my day. In the summer, for example, I often reserve Tuesdays for field trips with my grandson. At the same time, I don’t treat weekends as sacred or off-limits—I’ve never embraced the Monday-to-Friday, 9-to-5 model. In fact, I often work on weekends because there are fewer distractions and more quiet focus time.
I’m intrinsically motivated to complete the priorities I’ve set for myself, and I take time off when I need it. The constructs of weekdays or office hours don’t really exist in my world. I’ve developed a strong awareness of when I need to buckle down—and when I can afford to take a break.
But it’s not always about choice. Sometimes life throws you a curveball—a spouse recovering from surgery, an aging parent needing daily care, or a child who’s suddenly home sick for a week. In a traditional job, you might lean on sick time or paid family or medical leave. But when you’re self-employed, there’s no safety net. The flexibility to be there is a gift, yes—but it often comes with a steep cost. Client work pauses. Invoices stop flowing. And the stress of wanting to help while watching your income dry up is a reality many solopreneurs don’t fully anticipate. It’s one of the hidden emotional taxes of being your own boss.
Money: Feast, Famine, and the In-Between
Here’s where things get real. Cash flow is the lifeblood of any business, but it’s especially volatile when you’re self-employed. You may have a great month followed by a month where all you hear are crickets. You need to be ready for that.
Budgeting becomes more than just a suggestion—it’s survival. Track every dollar. Know your burn rate. Build an emergency fund. Plan for taxes. And make peace with the fact that your income will likely be irregular. That’s okay. It’s part of the rhythm. In fact, it is during the slow times that you spend more time working “on” your business rather than “in” it.
Also, think long-term. Just because you’re self-employed doesn’t mean you should ignore retirement. Open a solo 401(k), contribute when you can, and automate what you can. No one’s going to do it for you.
The Benefits Black Hole
Let’s talk about the stuff no one misses until it’s gone: benefits. Health insurance, paid time off, and disability coverage. When you’re on your own, all that safety net stuff becomes your responsibility.
It’s not impossible to find good coverage, but it takes time, research, and usually more money than you’d like. Look into your state’s health insurance exchange, see if any professional groups or trade associations offer plans, and seriously consider an HSA if you qualify.
It’s not fun. But it’s necessary.
You’re Not Alone—Unless You Choose to Be
Self-employment can be isolating, especially if you’re used to the camaraderie of an office. You’re the boss, the IT department, the janitor, and the coffee runner. But that doesn’t mean you have to do it alone.
Surround yourself with people who get it. Join networking groups. Create a small circle of fellow freelancers or business owners with whom you can bounce ideas off. Find a mentor or a coach. And don’t underestimate the value of a good mentor or accountability partner—someone who helps keep you focused when the grind gets rough.
The Learning Never Stops
Finally, self-employment is one long, winding course in personal and professional development. You will have to learn on the fly—new skills, new tools, new ways of thinking. And here’s the kicker: the time and money you invest in learning now fall entirely on your shoulders.
You don’t get paid for training days. There’s no HR department footing the bill for conferences. If you want to stay sharp and competitive, you’ll need to make space for learning—and budget for it too. That might mean buying courses, upgrading your software, attending events, or carving out a few hours to read or watch a tutorial.
You don’t need to master everything, but you do need to stay curious. Watch webinars. Read. Take courses. Learn from your mistakes. Stay humble enough to admit what you don’t know and bold enough to go figure it out.
Conclusion
If you’re on the path to self-employment—or already walking it—know that you’re not alone. It’s hard. It’s freeing. It’s messy. And it’s deeply rewarding if you stick with it and do the work. I hope that these lessons help you prepare, adapt, and thrive.
Now that you know what it truly takes, what’s your next move?