10 Years of Self-Employment: Here’s What I’ve Learned

He was wearing his “Thomas the Tank Engine” pajamas that morning.

I can’t remember if the character on the shirt was Thomas. Maybe it was Gordon or Percy.

All I remember is how much he loved those jammies.

“Here you go, buddy,” I said as I handed him his milk.

“Thank you, Daddy!” my oldest son replied.

He was three years old. I was his hero. And he was happy to be up early, hanging out with me, watching cartoons and having some breakfast.

So was I.

I had just quit my day job to freelance full time—something I had been planning for years. Naturally, I was elated. And now that I had finally done it, I finally felt a great sense of peace.

No more sales quotas. No more shifting compensation plans. No more internal politics.

It was my show now.

That was 10 years ago this week. June 1, 2006. The first day of my career as a self-employed professional.

It doesn’t seem like it’s been that long. You know how it is; the older you get, the faster time seems to fly.

It’s been a wild ride, for sure. I’ve learned a lot about running and growing a business. And I’ve learned a tremendous amount about myself.

What follows is a summary of the lessons I’ve learned during this journey. Wherever you are in your freelance career, I hope you’ll find some ideas and inspiration here.

The Leap Is Always Scary

My journey to self-employment wasn’t easy. I had a demanding, high-paying sales job, and I was my family’s sole breadwinner. So I didn’t have the luxury of extra time or a second income to help fund this experiment.

That’s why I mapped out and followed a very specific plan of action over a 27-month period. This plan required careful execution. It involved taking action every day, and it called for having a year’s worth of living expenses stashed away.

In May 2006, I had met my financial targets. I had the savings I needed, the steady work, the confidence and the plan to move forward.

Yet the weekend before I was going to submit my resignation, I was suddenly stricken with fear. What the heck was I doing? Was I really going to put it all on the line? Was this madness?

A bit of context: My employer had just been acquired by a much larger company. Most of us got to keep our jobs. The pay was about the same but the benefits package was much better. And the potential for upward mobility in this new company was very attractive.

So, yeah. I was having serious doubts about making this move. I feared that I’d be walking away from an excellent career opportunity.

The more I thought about it, the more I panicked. So I asked my wife for guidance.

“Have the circumstances changed?” she asked. “In other words, are your reasons for going out on your own still valid?”

“Yes, they are,” I replied.

“Then do it. Because if you don’t do it now, when will you do it?”

I love my wife. She’s a brilliant woman, and she was 100 percent correct.

If not now, when?

There’s never a perfect time to strike out on your own. So don’t sit around waiting for the stars to align.

I later discovered that this last-minute panic attack is very common when making big decisions. Maybe it’s some sort of survival mechanism—your lizard brain doing one last gut check before you jump off the cliff.

So if you find yourself in a similar predicament, re-evaluate your core reasons for making that decision. Have the factors changed? If they haven’t, stick to your plan.

Incidentally, within three years of my leaving that big software company, all but two of my colleagues had left or been laid off. (Something about a shift in priorities and direction within that organization.)

Don’t Quit Your Day Job

We tend to idolize people who make incredibly gutsy moves to start a business. We love to hear about the brave souls who put it all on the line to pursue their dreams. I guess it’s a common theme in Western culture, especially in America.

Of course, it’s the success stories we pay attention to, not the failures. The folks who crashed and burned by following a reckless strategy don’t seem to get much coverage in the media.

(And that’s a shame. Because we can all learn much from them.)

If you do something crazy and survive, you’ll have an amazing story to tell. But if you don’t make it, the price is often high. Especially if you have a family or other responsibilities.

Fortunately, you don’t have to risk everything. You can build your freelance business on the side while you keep the relative safety of your day job.

Yes, it’s more work. You’ll have to cut way back on Netflix binge-watching, college football and Facebook. You’ll have to say “No” to a few tempting invitations on the weekends. And you’ll get less sleep.

But this kind of bootstrapping will give you the “runway” you need in order to get your business off the ground the right way.

Keep your paycheck. And grow your side hustle until you’ve built enough savings to make the leap safely.

Create and Follow a Plan (…Sort Of)

Here’s the thing about planning. You need a plan when you want to accomplish something big — whether that’s launching a freelance business, taking your existing freelance practice to the next level or pivoting into a different business model.

But you also need to know when to throw your plan out the window.

A plan provides the vision and guidance you need day by day and week by week. But life doesn’t always work that way. Things happen. Priorities change. And big opportunities sometimes come along that force us to rethink our plan.

For instance, when I launched my freelance business in 2003 I billed myself as a lead generation specialist for B2B companies in general. But a few months later I refined my positioning to focus on enterprise software companies.

Within a year, I had abandoned the whole lead generation focus and was writing educational marketing content almost exclusively.

Why? Because that was the kind of work my clients were awarding me. So I took it!

Then, in early 2008 I wrote an e-book about how to safely make the transition from full-time day job to full-time freelancing. That e-book took off, and it helped me launch a side business selling instructional materials on how to land better clients.

Four years later I pivoted to focus most of my time and energy training and coaching other freelancers. And today, 95 percent of my income comes from teaching and coaching others how to earn more in less time doing work they love for better-paying clients.

It hasn’t always paid as well as my traditional freelance business has. But it’s what I most love to do.

My point? This wasn’t my original plan in 2003 when I started my part-time freelance business. But I continued to carefully pivot as I paid attention to what I enjoyed doing most and what was working for me.

So the lesson here is to be open to life’s little serendipities.

The best opportunities aren’t always the ones we carefully plan. They often show up unannounced.

And if you’re not paying attention (or if you’re obsessed with sticking to your plan), you may miss some great opportunities.

Imbalance Is Normal

The whole “work/life balance” thing has become a bit of a cliché. I think most of us get it: It’s not healthy to work too much or to rest too much. You need a balance.

It makes perfect sense. Until you’re facing multiple tight deadlines, intense pressure to land a new client and a newsletter you’ve been trying to publish for two weeks.

Here’s what I’ve learned: Imbalance is the normal state in our lives, not balance.

And if you try to create balance in your life every day, you’ll be sorely disappointed. This will often create even more anxiety, which leads to guilt, which creates more imbalance.

My struggle — and I don’t think I’m alone here — is not so much about finding balance as it is about ensuring that a hectic pace doesn’t become my new norm.

Because after a while, the level of intensity that once felt abnormal starts to feel very normal. And before you know it, that’s your new normal state. So when you try to disengage from work, it becomes very hard to stay fully present.

Hard work and long hours have become your new security blanket.

Self-employment is supposed to give you a level of freedom you didn’t have as an employee. But over the past 10 years I’ve also learned that it can become its own prison if you’re not careful. 

This is something I’m constantly battling. I started my business in large part to spend more time with my family. Yet I often find myself working longer hours than I did when I worked for someone else.

Awareness is the first step to change. I’m fully aware that this is a weakness of mine, so I have to monitor myself closely and set and follow personal rules that will keep me out of trouble.

The Comparison Trap

During my first few months of self-employment, I often felt guilty. I felt guilty for friends who had to endure jobs they hated. And I felt bad for aspiring copywriters I knew who were still barely scraping by.

Along with that guilt came a strong feeling of gratitude. I was thankful for the opportunity to do this. I was grateful for my clients, for my mentors and for having the gumption to give this a shot.

But it didn’t take long for me to start comparing myself to other freelance professionals. Some were doing better than I was. Or they had better-known clients. Or they were working on more interesting projects.

I also started questioning my choice to go solo. Especially when I saw that some of my ex colleagues were now advancing rapidly through the corporate ranks. Years ago we were all equals. Yet some of them were now in executive-level roles, traveling the world, cashing in stock options worth hundreds of thousands of dollars.

And I wondered: Did I make a mistake? Did I choose the foolish path?

I’m very achievement-oriented. It’s how I’m wired. So these thoughts still creep in from time to time. But I’ve also learned that comparing yourself to others is not healthy. Nothing good comes out of it.

These comparisons are never fair. In virtually every case what we’re doing is taking the best aspects of someone else’s situation, with the bad elements of that scenario removed. And then we’re comparing them to the worst parts of our own circumstances.

When the mental game we play is this rigged, of course we’re going to feel inferior and inadequate!

So the lesson I’m still trying to learn is simple:

Don’t compare. This is not a race. It’s not a contest. And if you choose to make it so, you’re always going to lose.

It Really IS About the Journey

If there’s one lesson I’ve resisted learning all these years, it’s this:

You never really “arrive.” There’s no magical income level that’s going to solve all your problems.

You’ve heard this advice many times before. But here’s the clarification I’d like to make:

Every time I heard this “it’s the journey that counts” advice, it seemed to come from a financially successful person. 

“Well, of course you’re saying that. You have plenty of money,” I would say to myself. “You’re comfortable. So you have the luxury of pontificating on such things. I, on the other hand, have bills to pay!”

Now that I’ve met and exceeded some of my biggest income goals, I can tell you without reservation that the advice is solid. Because no matter how much you earn, you’ll always have challenges.

Your problems don’t end when you reach $80,000 or $100,000 or $200,000 in income. You just have different problems.

So rather than obsessing over a big goal, try your best to enjoy the journey to that goal.

The late Jim Rohn said it best: The biggest value of a goal is not its achievement. The biggest value is the person you become in the pursuit of that goal.

Enjoy the journey. And make sure it shapes you into the person you want to become.

You Get What You Expect

I used to think that successful entrepreneurs got to where they are because of talent and intelligence. But one of my biggest discoveries over the past 10 years is that talent and IQ will take you only so far. While you need a minimum amount of each, there are other factors that will determine your success in business.

Here’s one of the most important traits successful solo professionals have in common: They are certain about their outcomes. Or at least more certain than the average person trying to achieve the same goal.

I call it the Law of Certainty:

Whatever you believe with total certainty will manifest itself (assuming that you take smart and steady action).

When you think about it, certainty is nothing more than a very strong belief. When we’re certain of something, there’s no doubt about that thing. It just “is.”

And guess what? You’re applying this law every single day. There are many things about which you’re already certain. The question is, what are those things?

I’m certain that my car is going to start tomorrow morning. And that there’s milk in the fridge. And that the light will come on in my office when I flip the switch.

I also have similar beliefs about how my business will do over the next few months.

When I look back at my best income years as a freelancer, and when I think about the top performers I’ve coached, three important realities emerge:

1. Big results are no big deal. I expected to continue to earn a high income. I didn’t overthink it. I didn’t get anxious about it. It felt normal to me.

2. I’m providing real value. I’ve always believed that I was providing a valuable service to the market. Overall, I didn’t feel weird about charging premium fees because I knew that my clients were getting serious value. (Sure, sometimes I felt a bit fearful about raising my fees. But for the most part I’ve felt good about what I charge.)

3. There’s an abundance of work out there. I didn’t worry day and night about my work pipeline. Instead, I trusted that the work would continue to flow. That didn’t mean I stopped prospecting. It just meant that generally I wasn’t worried about the work drying up. I knew that it was out there and I just needed to find it.

Yes, I’ve had my dry spells like everyone else. But I’ve also noticed that these dry spells were precipitated by a shift in my beliefs. When I started doubting myself and fearing the worst, bad stuff started to happen. Which, in turn, caused me to expect more bad things. And that created a self-fulfilling downward spiral.

Belief is the key. Which is why working hard to generate a positive result—any positive result—is so important.

Because a positive result creates positive thought, which helps improve our beliefs, which motivate us to take action, which leads to even more positive results.

Just Because You Can’t See It Doesn’t Mean It Doesn’t Exist

Along those same lines, I’ve discovered that our reality is very subjective. Just because we’re not earning what we’d like earn doesn’t mean that the higher-paying work is not out there. And just because our current clients treat us poorly doesn’t meant that better clients don’t exist.

I learned this lesson when my business took a big hit in 2008. After a few months of barely scraping by, I was quickly losing hope. And I really believed that there was no work out there.

That’s until, out of nowhere, I landed a $19,000 gig with a new client. Within a week of cashing the deposit check, my perception about the market had changed completely.

Here’s what I know: I still turn down work every month from prospects who contact me, and I refer them to colleagues who could serve them. I also know dozens of writers and copywriters who are currently booked solid with high-paying work.

That’s never changed, even during hard times.

There’s always plenty of good work out there. Just because we don’t have some, that doesn’t mean it doesn’t exist.

The Freelance Opportunity Pyramid 

One of the most interesting insights I’ve learned since going out on my own has to do with the dynamics of the freelance marketplace.

Not all freelance work is created equal. And not all clients have the same needs, expectations or willingness to pay good fees. Instead, there are four different categories within the marketplace:

1. Bargain-basement: This is where clients expect 1,000-word articles for $10 (or less!).

2. Vendor: The pay is higher, but you’re still in a very competitive situation. The client is mostly worried about price, not about who would be the best writer for the job.

3.Trusted Expert: Price is a factor but it’s not the top factor. The client is more concerned with overall experience, track record, dependability and other “soft” factors.

4. Rock Star: This is the top of the pyramid. Fees are not an issue. The client knows that the freelancer is worth every penny. It’s more common in situations such as direct-response copywriting, where the ROI is easily measured and the freelancer can help move the needle in a big way. There are only a handful of clients willing and able to hire rock stars. And there are even fewer freelancers who qualify for the title.

Once you understand that the market is divided into categories, you stop worrying about the low-priced competition and the rise of low-cost overseas freelancers. 

That’s when you realize that the sweet spot is the “Trusted Expert” sector. So you put forth the effort to establish yourself in this category and focus on value and other differentiators that are important to your target market.

I published a podcast episode on this topic, if you’re interested in learning more about this concept and how to apply it in your own business.

The Sunday Night Litmus Test

I used to dread Sunday nights when I had a day job. That’s when I’d start thinking about how I had to do it all over again the next morning.

But for the past 10 years, I’ve noticed that I no longer get depressed on Sundays. I look forward to Monday mornings. (Seriously!)

And that’s a great sign that I’m doing what I was put on this earth to do.

I encourage you to apply this Sunday night litmus test. As you continue your freelance journey, ask yourself: Am I typically happy and excited about the upcoming week, or am I dreading it?

If the feeling is usually more negative than positive, don’t ignore it. Find out what’s causing the pain.

But if the feeling is generally positive, consider it a sign that you’re on the right path.

Breakfast: 10 Years Later

Back to breakfast with my son. It’s been 10 years since that morning. He’s 13 now.

Just last week he came down for breakfast before leaving for school. And, boy, how things change!

He still was half asleep, wearing a black Green Day T-shirt (yes, the band from the 90s; don’t ask), black jeans, black Converse All-Stars and a beanie hat.

I was already in the kitchen, but he didn’t ask me to give him milk or cereal. He served himself.

A few moments later, he was done. He put his dishes in the sink (where apparently they wash themselves). And he gave me a goodbye hug on his way out to school.

“I love you, buddy,” I told him.

“I love you, too, Dad,” he replied.

Life is good.