Lessons from Running a Business for 16 Years

I started my first business at sixteen. Not because I had a grand vision. Because I hated depending on other people for money. That simple discomfort led to sixteen years of building, failing, rebuilding, and eventually figuring out what actually works.

Most business advice comes from people who’ve read about business. This comes from someone who’s lived it. I’ve made expensive mistakes. I’ve had months where client payments didn’t come through and rent was due anyway. I’ve also had years where revenue grew 104% without me adding a single hour of work. The difference between those two states came down to a handful of lessons that took way too long to learn.

Here’s what I wish someone had told me at the start. For the practical tools behind these lessons, check my guide on must-have tools for freelancers.

Cash Flow Is Everything

Revenue means nothing if you can’t pay your bills this month. I learned this the hard way in my third year of freelancing. On paper, I had $12,000 in outstanding invoices. In reality, I had $340 in my bank account and rent due in a week. That gap between money owed and money received nearly killed my business before it really started.

The problem wasn’t the work. Clients were happy. Projects were successful. The problem was that I’d agreed to net-60 payment terms because I wanted to seem professional and accommodating. Two months is a long time to wait when your hosting bill is due now.

After that scare, I changed everything about how I handled money. Net-15 became my standard. Deposits upfront became non-negotiable. I started tracking cash position weekly, not monthly. When you know exactly how much money you have and when money is arriving, you stop making desperate decisions. You can say no to bad clients. You can wait for good opportunities. Cash flow gives you options, and options are what separate surviving businesses from thriving ones. For tracking all of this, best accounting software makes the job manageable.

Your First Clients Won’t Be Your Best Clients

Early in my career, I took every project that came my way. Someone needed a logo for $50? I was on it. A local restaurant wanted a website but could only pay in gift cards? Sure, why not. I said yes to everything because I needed the work and I needed the experience.

Those early clients taught me a lot, but mostly they taught me what I didn’t want. The $50 logo client wanted seventeen revisions and called me at 10pm on weekends. The gift card restaurant never referred anyone and complained about the website for years after I’d finished it. Meanwhile, the one client I’d charged properly, a small software company that paid $2,000 for their site, sent me three referrals in the first year. Each of those referrals became bigger projects than the original.

There’s a direct correlation between what clients pay and how they treat you. The clients who pay the least demand the most. The clients who pay fairly respect your time and expertise. This isn’t always true, but it’s true often enough that you should build your business around it. Stop chasing small checks from difficult people. Find the clients who value what you do and double down on serving them well.

Systems Beat Talent Every Time

I know talented people who struggle financially. I know mediocre people who’ve built successful businesses. The difference isn’t luck. It’s systems. Talent gets you started. Systems get you paid consistently.

When I was doing everything manually, I could handle maybe eight clients at a time before quality started slipping. Emails would go unanswered for days. Invoices would go out late. Follow-ups would fall through the cracks. I was working constantly but dropping balls everywhere.

Then I started systematizing. Templates for proposals. Automated follow-up sequences. A project management board where nothing gets lost. Recurring calendar blocks for different types of work. Within six months, I was handling fifteen clients with less stress than I’d had with five. The systems didn’t make me more talented. They made my talent more reliable. And reliability, more than brilliance, is what clients pay for. For the tools that enable this, see best project management tools for teams.

Raise Your Prices Before You’re Ready

I waited too long to raise my rates. By the time I finally did, I’d spent three years undercharging and attracting the wrong clients. The moment I increased my prices by 40%, something weird happened. I lost two clients who complained about the increase. I gained three new ones who never questioned the higher rate.

Net result: more revenue, better clients, less stress. The clients who pay more expect more, but they also trust your expertise more. They don’t question every decision or demand constant updates. They hired you because you’re good at what you do, and they let you do it.

If you haven’t raised your rates in two years, you’ve given yourself a pay cut. Inflation eroded your margins while your skills improved. You’re literally worth more than you’re charging. The only thing stopping you from charging more is your own fear that clients will say no. Some will. The ones who stay, and the new ones who come in at higher rates, will make up for it and then some. See the complete guide to raising your rates for strategies.

Specialization Multiplies Your Value

Generalists compete on price. Specialists compete on expertise. I spent my first five years as a generalist, doing logos, websites, SEO, social media, content writing, whatever clients needed. I was decent at all of it but great at none of it. That meant I was always competing with someone cheaper.

When I specialized in WordPress performance and monetization, everything changed. I could charge more because fewer people did exactly what I did. I could work faster because I solved the same types of problems repeatedly. I could market more effectively because my message was specific instead of vague. Instead of “I do digital marketing,” I could say “I help content sites load faster and make more money.” That specificity attracted clients who had exactly those problems and were willing to pay for solutions.

Specialization feels scary because you’re turning away potential work. In practice, you’re trading a wide pool of low-value clients for a smaller pool of high-value ones. The math works out in your favor almost every time. For WordPress specifically, my WordPress freelancing guide covers specialization in depth.

Your Network Is Your Net Worth

The best opportunities I’ve had didn’t come from cold outreach or marketing. They came from people I’d helped years earlier. A client I did a $500 project for in 2015 referred me to a company that became a $40,000 annual retainer. A podcast guest I helped with technical issues introduced me to a partnership that still generates passive income today.

Relationships compound like interest. Every person you help genuinely, without expecting anything back, becomes a node in a network that can open doors you didn’t know existed. This isn’t about being fake or strategic. It’s about being genuinely useful and trusting that good things come back around. They almost always do, just not immediately and not always from the direction you expect.

I make it a point to help at least one person per week with no expectation of return. Sometimes it’s answering a question. Sometimes it’s making an introduction. Sometimes it’s giving honest feedback on their work. The time investment is minimal. The long-term returns have been massive.

Saying No Is a Skill

Every yes to the wrong thing is a no to the right thing. I didn’t understand this for years. I’d take on projects that weren’t a good fit because I was afraid of turning down money. Those projects always took longer than expected, paid less than they should have, and drained energy I could’ve spent on better opportunities.

Learning to say no was uncomfortable at first. It felt like I was leaving money on the table. But the opposite was true. Every bad project I declined opened space for a good one to come in. Every client I turned away for being a poor fit led me to find one who was a perfect match.

The filter I use now is simple: Would I be excited to do this work at this price for this person? If any of those three elements is off, I pass. Life is too short to spend it doing work you resent for people you don’t enjoy at rates that feel insulting.

Health Is a Business Asset

I ignored my health for the first decade of running my business. Late nights, junk food, no exercise, constant stress. I told myself it was necessary for success. That was a lie I told to justify bad choices. When my health finally caught up with me, productivity crashed. I spent more on doctors than I would have spent on prevention. Worst of all, the quality of my thinking degraded when I needed it most.

Now I treat health like a business investment. Sleep is non-negotiable. Exercise happens every day, even if it’s just a walk. Food is fuel, not entertainment. When I’m healthy, I make better decisions, work faster, and handle stress more effectively. When I’m not, everything suffers.

If you’re running on empty, you’re not being dedicated. You’re being foolish. Your business needs you functioning at your best. That means taking care of the machine that runs it.

Most Failures Are Recoverable

I’ve launched products that nobody bought. I’ve lost clients over stupid mistakes. I’ve made financial decisions that cost thousands. Every single one of those failures felt catastrophic at the time. Looking back, none of them were. The product failure taught me to validate before building. The lost clients taught me to communicate better. The financial mistakes taught me to track everything.

When you’re in the middle of a failure, it feels permanent. It’s not. Most business failures are recoverable if you learn the lesson and adjust. The only unrecoverable failure is giving up entirely. Everything else is just expensive education.

The Long Game Always Wins

I’ve watched people chase quick money and burn out in two years. I’ve watched others build slowly and compound their way to success over a decade. The slow builders almost always win. Quick money usually comes with hidden costs: reputation damage, client relationships that can’t be maintained, or business models that don’t scale.

The boring path of doing good work for fair clients, year after year, builds something that lasts. Each year adds to your reputation, your network, your skills, and your income. The compounding effect is invisible at first but undeniable after ten years.

I’m not where I am because I had a breakthrough moment. I’m here because I kept showing up for sixteen years. I got a little better each year. I built on previous work each year. I maintained relationships each year. Success in business isn’t about one big win. It’s about accumulating small wins until they add up to something significant.

Know When to Walk Away

Not every project should be finished. Not every client relationship should be maintained. Not every business model should be saved. Sometimes the best decision is to cut your losses and move on.

I’ve ended projects that weren’t working. I’ve fired clients who made my life miserable. I’ve shut down revenue streams that weren’t worth the effort. Every time, walking away freed up energy and resources for something better. The sunk cost fallacy will tell you to keep going because you’ve already invested so much. But throwing good time after bad investments doesn’t make them good. It just makes the hole deeper. Learn more about how to fire a client the right way.

Know when to pivot. Know when to stop. Know when the lesson has been learned and it’s time for the next chapter.

Simplicity Beats Complexity

Every time I’ve made my business more complicated, I’ve regretted it. More services, more tools, more processes, more overhead. Complexity feels like progress but usually just creates problems.

The businesses that work best are simple. One core offering, done well. One target market, understood deeply. A handful of tools that actually get used. Processes that can be explained in a paragraph.

When I stripped my business down to essentials, profitability increased even as revenue stayed flat. The math is obvious in hindsight: fewer moving parts means fewer things breaking. Focused effort beats scattered attention.

Now I actively resist complexity. Every new service, tool, or process has to justify its existence. Most don’t.

Luck Matters More Than You Think

Hard work is necessary but not sufficient. I know people who worked harder than me and failed. I know people who worked less and succeeded spectacularly. The difference often came down to timing, connections, or circumstances none of us controlled.

This isn’t an excuse to stop trying. Effort creates opportunities for luck to matter. But acknowledging luck’s role keeps you humble when things go well and resilient when they don’t. Success doesn’t mean you’re smarter than those who struggled. Failure doesn’t mean you’re less capable than those who thrived.

Do the work. Stack the odds in your favor. But remember that randomness plays a larger role than any of us want to admit.

Your Business Reflects You

Over sixteen years, I’ve noticed that businesses tend to reflect their owners. Chaotic people build chaotic businesses. Organized people build organized businesses. Generous people attract loyal customers. Difficult people attract difficult clients.

This is both empowering and uncomfortable. If your business has patterns you don’t like, look at yourself first. The problem is rarely “out there.” It’s usually in how you’re showing up.

When I worked on myself, my business improved. Better boundaries in personal life translated to better boundaries with clients. Clearer thinking translated to clearer offerings. More patience translated to better relationships.

Document Everything

The knowledge in your head isn’t an asset. It’s a liability. If only you know how something works, you’re a single point of failure.

I started documenting processes late, and I paid for it. Every time I needed help, I had to explain everything from scratch. Every time I took a vacation, things fell apart because nobody knew what to do.

Now I document obsessively. Standard operating procedures for recurring tasks. Templates for common deliverables. Knowledge bases for client information. The documentation takes time to create but saves far more time over years.

Plus, documented businesses are sellable. Businesses that live in the owner’s head can only be shut down.

Recurring Revenue Changes Everything

The most stressful years of my business were when every month started at zero. No matter how good last month was, the slate wiped clean. I had to sell constantly just to maintain position.

Building recurring revenue changed the game completely. Retainers, subscriptions, and ongoing agreements mean each new month starts with a foundation. The compounding effect is powerful: add one retainer, and it keeps paying. Add another, and the base grows. Eventually, you’re building on something instead of rebuilding from nothing.

If your business model allows recurring revenue, pursue it aggressively. The stability it provides is worth almost any tradeoff.

You Don’t Need Permission

Early in my career, I waited for permission that never came. Permission to charge more. Permission to say no to bad clients. Permission to pivot my business model. I thought someone would validate my choices.

Nobody did. Nobody does. The permission you’re waiting for doesn’t exist. You’re the one running the business. You make the decisions.

Some decisions will be wrong. That’s fine. Wrong decisions you own are better than good decisions you waited for approval to make. The waiting is usually more costly than the mistakes.

Automation Is Underrated

Every task I’ve automated has paid for itself within months. Email sequences that run without me. Invoices that send themselves. Social posts that schedule in advance. Reports that generate automatically.

The cumulative effect of small automations is massive. Each saves maybe 30 minutes per week. Ten automations save 25 hours per month. That’s weeks of time back over a year.

Look at everything you do repeatedly and ask if software could do it instead. The answer is usually yes, and the investment is usually worth it.

Business Is Personal

The idea that you should separate business from personal is naive. Your business is deeply personal. It affects your stress, your relationships, your sense of identity. Pretending otherwise doesn’t change the reality.

This means business problems become life problems. But it also means solving business problems improves your life. The skills you build, the discipline you develop, the resilience you gain, these transfer everywhere.

Embrace the personal nature of business. Build something you’re proud of. Work with people you respect. Create impact that matters to you. Business that’s just business isn’t sustainable long-term.

Final Thoughts

Sixteen years isn’t that long in the grand scheme of things, but it’s long enough to see patterns. Long enough to watch what works and what doesn’t. Long enough to make most of the common mistakes and learn from them.

The lessons above aren’t theories. They’re what I learned by getting things wrong first. If even one of them helps you avoid a mistake I made, this article was worth writing.

Business is simple, but it’s not easy. Do good work. Charge what you’re worth. Take care of your health. Build relationships. Play the long game. Trust the process even when results are slow. Learn from failures without being defined by them.

The sixteen years ahead will bring new lessons I can’t predict. That’s what makes this interesting. Every phase of business brings different challenges and different growth. I’m looking forward to the lessons year twenty will teach me.

Everything else is details.