For many people, putting things off is second nature. We’re always waiting for that perfect timing—going back to school, getting married, having kids, buying a house, and yes, even starting a business. 

I get asked some form of the same question all the time since starting my business. What took you so long? Why didn’t you do it sooner? And honestly, my answer was always that the stars had not yet aligned. A reason always kept me from pursuing my dream of being a full-time writer. 

I didn’t think I had the chops to manage my own business. I didn’t have confidence in my ability to be my own boss. There was the fear that I wouldn’t be able to offset the income I was bringing in through more traditional employment. You name it. I had a reason why I couldn’t do it. 

While it is true that the stars finally did align for me and the perfect timing came for me to start my business—it practically fell in my lap—I want to caution people that if they wait too long, they might miss a golden opportunity. Why? Because I firmly believe that people are meant to live out their dreams. And what’s the worst thing that can happen? Do we fail? Yes, that’s a risk. But we won’t know until we try.

Why We Push Off Our Dreams: It’s a Psychology Thing

Many people fail to pursue their dreams because they are afraid of failure. And yes, that fear lived and breathed in me. But honestly, it wasn’t the all-consuming barrier that kept me from doing what I really wanted to do all the time—write (and read a great book now and again for good measure). The biggest obstacle that got in my way was the fear that I wouldn’t generate the income I needed. I wouldn’t bring in the money that my family had come to rely on.

So, instead of trying things on for size, I kept my passion for writing in the background. When Experian, yes, one of the three credit bureaus in the U.S. and the company that I worked for from 2012 to 2015, started a blog, I signed up to be a contributor. When Sutherland Global Services, the company I worked for from 2015 to 2018, needed content rewritten—I took the challenge head-on. Of course, it wasn’t all that challenging to do when I was responsible for industry marketing, and we needed content to share.

When I worked for a small online lender from 2019 to 2023, my favorite part of the workday was writing blogs or overseeing blog creation for the company’s external website. I found a way to live in my happy space, even though I wasn’t doing it on a day-to-day basis.

The challenge was that the longer I kept myself from doing what I loved to do, the unhappier I became in my career. And that’s the thing. When you find yourself doing a job you don’t love, no matter how good you may be, you do yourself and everyone around you a disservice. And trust me, all the money in the world isn’t going to give you the happiness that you can find when you get to do what you love to do every day.

But why do we let these fears hold us back? What is it that keeps so many of us from diving into what we’re passionate about? The truth is, it often comes down to a mix of psychological reasons that can quietly convince us to stay put. If this sounds like you, take a look at some of these common mental roadblocks that might be standing in your way.

I know I hit on some of these earlier, but humor me while I organize and lay it all out on the table.

• Fear of Failure: This is probably the biggest one. We worry about what happens if things don’t work out, and that fear can paralyze us into inaction. And, while I know I talk about this a lot in my blog on my business website, Copywriting For You, there is a sad reality out there—20% of businesses fail in their first year. Perhaps even more alarming is that only half of businesses are still standing after five years. 
• Comfort in Familiarity: Even if you’re not entirely happy, the comfort of what you know can keep you from taking the leap into something new and uncertain. But I warn you, getting too comfortable can lead to complacency. And that can lead to stagnation. And that’s not good.
• Imposter Syndrome: The nagging feeling that you’re not good enough or that you’re just faking it can make you doubt your abilities, even when you’re fully capable. I’ll be honest; I’ve had a pretty successful career if I do say so myself. I had made my first million by 2010, which I think is pretty impressive considering I didn’t graduate from college until 1998. And I’ve hit that million-dollar mark a few more times since then—something I am quite proud of. This isn’t to be a “wow, look at me” exclamation by any means. Rather, it’s almost my way of saying to myself that I’m no imposter. When I put my mind to things, I’m good at it.
• Lack of Resources: Whether it’s time, money, or skills, the belief that you don’t have what it takes to succeed can stop you before you even start. But if you are looking to start a business as a writer, all you really need is a notebook, pen, and a really good laptop. 
• Overthinking: Sometimes, we get so caught up in analyzing every possible outcome that we talk ourselves out of taking any action at all. I have talked about the concept of analysis paralysis before in the context of endless client revisions. But it applies here, too. I found myself so caught up in all the reasons that starting my business wouldn’t work that I forgot to think of all the reasons it would.
• Fear of Judgment: Worrying about what others might think if you fail—or even if you succeed—can be a major barrier. In my case, a bit of fuel was added to the fire based on the income expectations that my former spouse seemed to have. He was a chronic spender, always looking to buy the next thing. As such, I feared disappointing him. Before I knew it, I found myself pushing aside my own career dreams and instead looking for bigger and better incomes to help fund his passions rather than my own.
• Procrastination: Putting things off because the task seems too big or you’re waiting for the “right” moment can indefinitely delay your dreams. For me, my procrastination consisted of all the things earlier in this list. I let those things hold me back, thus pushing out the opportunity further and further. 

The Cost of Waiting

So, what’s the risk of waiting? What is the actual cost of doing so? No, this is not meant to be a financial computation, though you can certainly do the math if you want to.

The cost I am talking about is the cost to you as a talented individual who has more to offer the world—someone who has more to offer themself. Trust me here. The real cost of waiting is about more than just dollars and cents. It’s about the missed opportunities that could have helped you grow, both personally and professionally. 

By waiting until January 2023 to finally make the leap and turn my side hustle into a full-time gig, I lost valuable time that could have been spent building my brand, expanding my network, and honing my skills in a highly competitive industry.

Everyone is vying for attention in the content writing space, and starting sooner could have given me a head start in growing my social media presence and establishing my name as a go-to writer. The earlier you jump in—not just get your feet wet—the more time you have to create connections, gather testimonials and show the world what you’re capable of. Trust me, there’s plenty of room for talented writers, but it takes time to carve out your space.

Then there’s the regret factor. Sure, the risk of failure is real—anyone who’s started a business will tell you that. But compare that to the regret of never trying at all. What if you wait too long and miss out on the chance to do something amazing? The long-term consequences of inaction can weigh heavier than any potential failure. You don’t want to look back and wonder, “What if I had just started sooner?”

And yes, let’s talk about the money. Delaying your start can also delay your financial independence. Every month you wait is another month of not earning what you could be if you were all in. It’s another month of not building the financial security of running a successful business. I’m not one of those content writers or copywriters who earn less than $100,000 per year. I’m good at what I do. I put my all into my work. And my compensation shows it. 

Plus, starting earlier means more time to navigate the ups and downs, learn from your mistakes, and eventually reach a point where your business is prosperous.

In short, the cost of waiting is high. The lost time, missed opportunities, and lingering what-ifs can hold you back from reaching your full potential. So, if you’re on the fence, consider this your nudge to start sooner rather than later.

The Realities of Starting a Business

Starting a business isn’t easy, and if you’ve been following along in this blog series, you’ve probably seen that firsthand. My goal has always been to share what I’ve learned so you can avoid the same pitfalls I encountered.

From the beginning, I made some rookie mistakes that cost me time, money, and a lot of stress. For instance, going cheap on a website left me with a design that didn’t represent my brand well. Not having clients sign a statement of work led to misunderstandings and unpaid invoices. Undervaluing my services hurt my bottom line, while not dedicating enough time to lead generation made finding clients more challenging—and hurt my pocketbook a bit in the process.

I also neglected to protect my business with liability insurance, which was a risk I shouldn’t have taken. Waiting too long to embrace social media meant I missed out on opportunities to build my audience. And let’s not forget the importance of regularly updating my blog—something I didn’t prioritize early on. Then there’s the balancing act with AI: relying too much or too little on it can both be a problem. Finally, I underestimated the power of business partnerships, which could have helped me grow faster and get in front of more of the right people.

These lessons were hard-earned, but they’ve shaped the business I have today, and I hope they help you build yours even better. Because, yes, building a business is a lot of work. It takes dedication and perseverance. You’ll give up some free time. You’ll need to establish some boundaries. But it is possible. And you can absolutely be successful.

Turning Your Dreams into Your Reality

How do you turn your dreams into reality? It all starts with setting reasonable dreams. Of course, we all want to win the lottery. Imagine those millions of dollars and all the doors it can open—a house up in the mountains or on the beach—maybe both. Never worrying about making ends meet. Moving out of that 66% of Americans who live paycheck to paycheck and possibly becoming one of America’s elite?

Winning the lottery has a probability of one in three million. Considering the U.S. population is just under 346 million at the time of this writing, you can see that this is just one of those dreams that might not become a reality. And while all you need to do is buy a ticket, the chances that you will get those numbers right on the right day, is just not that probable.

Going after a small business dream, on the other hand, is far more realistic. It’s achievable. And typically, the only thing getting in your way is yourself. All those reasons I laid on the table earlier in this article are keeping you from taking the steps of getting off the couch and getting started.

Do you think those who win marathons, or our Olympians, simply got up one day and said they would win a medal and just made it happen? Of course not. They worked for it. Training was non-negotiable. They did their homework. And most importantly, they owned their dream to make it a reality.

You can do this too. But if you keep pushing it off over and over again, it will never happen. 

Getting Started and Making It Happen

Making the decision to get started is where it all begins. Obviously. But what do you do once you decide you want to get into the copywriting business? You may already be panicking. How are you going to find customers? How are you going to make sure those leads start coming in? Will you be able to charge what you are worth, and more importantly, what rate should you start out at? 

You’ll have a lot of questions. And up front, you won’t have all the answers. One of the most beautiful things about the writing business is that you are always learning. So, anticipate that you will be learning a lot during your first several months. I’ve been writing as a side hustle since 2019, and I’ve been doing this full-time since the beginning of 2023. I can honestly tell you that I learn each and every day. I am constantly refining my approaches to managing my business to see what works and what doesn’t. You will, too.

So, with an open mind and a willingness to learn—and make mistakes—you’ll be well-positioned for success. That said, here is what I suggest you do to get started. It worked for me, and with some perseverance, I think it can work for you, too.

1. Decide What Kind of Writer You Want to Be

Take some time to think about what type of writing excites you the most. Are you drawn to creating persuasive copy for sales pages, crafting engaging blog posts, or developing technical content? Knowing your niche will help you focus your efforts and attract the right clients.

What kind of writing do I do? Well, my passion is in writing informative content—blogs and articles—for business websites. I write in both the B2B and B2C space, and I love the variety that this affords me. And while my business might be called Copywriting For You, the truth is that I spend most of my time content writing and less time copywriting. It’s just what I enjoy doing most, and my clients know it. So, that’s the work they throw my way.

2. Start Small and Build Your Portfolio

Begin by taking on small projects to build a portfolio. Don’t worry if they aren’t high-paying gigs at first—getting experience and having samples to showcase your skills matters. I’m a big fan of the Upwork platform to help you get your start. Thousands of projects are out there, just waiting for the right freelancer. And that freelancer could be you.

But Upwork isn’t your only option. You can find similar gigs on Fiverr, and you can market yourself on LinkedIn, too. You just need to find what works for you. There are also plenty of email newsletters that you can sign up for that give you a heads-up on companies looking for freelance writers.

3. Set Up Your Business Structure

Decide if you want to operate as a sole proprietor, LLC, or another business structure. Based on guidance from my accountant, I went with the S-corporation option. Each structure has its pros and cons, so it’s worth doing some research or consulting with a professional to see what’s best for you.

To that end, I suggest you get set up with an accountant before you get too far. Their advice is worth its weight in gold and can keep you out of trouble down the road.

4. Create a Professional Website

You guessed it—you need a winning website, and you can not do this on the cheap—unless you have website development and design experience. Your website is your online business card. Make sure it reflects your brand and showcases your work. Include a portfolio section, an ‘About Me’ page, and clear contact information. If you’re not tech-savvy—like me—investing in a good website designer can make a big difference.

5. Establish Your Rates

Pricing can be tricky, but you need to start somewhere. Research industry standards, consider your experience, and set rates that you’re comfortable with. Remember, it’s easier to raise your rates later than to lower them. Keep in mind, too, that if you stick to copywriting, you may be able to charge a higher rate than for content writing. Sales writing is designed to convert. As such, clients should be willing to part with the dollars that are spent to help them drive those conversions.

6. Develop a Marketing Plan

Think about how you’ll attract clients. This might include networking, social media marketing, email outreach, or even paid ads. Choose strategies that fit your budget and skills, and be consistent with your efforts. Don’t delay this. You need to start promoting yourself right away.

7. Start Building Relationships

Networking is key in this business. Reach out to other writers, join online communities, and connect with potential clients. Look for networking opportunities in your community. Consider joining your local Chamber of Commerce to make some business connections. Building genuine relationships can lead to referrals and repeat business.

8. Keep Learning and Improving

The writing industry is always evolving, so make it a habit to keep learning. This could be through online courses, reading industry blogs, or experimenting with new types of content. Coursera and Udemy both offer copywriting courses that can help you refresh your skills and get your head in the game.

9. Stay Organized

Staying organized is crucial for running a smooth operation, from managing deadlines to tracking invoices. Use tools like project management software, time trackers, and accounting apps to keep everything in order. Avoid relying on spreadsheets wherever possible. Trust me on this, multiple spreadsheets can become quite the headache come tax time.

10. Don’t Be Afraid to Make Mistakes

Mistakes are part of the learning process. Don’t be too hard on yourself if things don’t go perfectly at first. Learn from each experience, and use that knowledge to refine your approach as you go. Perseverance and persistence are where it’s at.

Want to Talk to Someone Who’s Been Down the Road You Are Traveling?

By now, you get my point—don’t delay pursuing your passion. If you have a talent that the world can benefit from, you’re doing everyone a disservice by not getting it out there. And the truth is that life is short. Why spend time doing something you don’t love when you can do what you do love?

If you want to talk to someone who has been down the same road, set up a marketing consultation today. I’m happy to share my story and listen to yours. After all, we can all use a few more connections, right?