How falling in love with your new business can ruin it

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The stupid decisions people make when starting a new business are a lot like the stupid decisions they make in their relationships.  The good news is, when you screw up, your business is a lot more likely to give you a second chance.

If this post helps you avoid or learn from some of the mistakes I made early on in my own business, it’s served its purpose.  If it helps you with your love life, keep it to yourself, because I don’t want to be known as a relationship guru.

The Dating Scene

Although I always knew I loved to write, I also had a passion for computers.  The latter wound up dictating the first decade or so of my professional career.  As with dating, trying out different jobs helped me learn more about myself, what my needs were, and what would make a good match.  I learned that I wanted to do work that helped other people,  involved problem solving, fostered my creativity,  provided fun challenges, and provided me enough of an income to live comfortably.  I found all of these qualities at different times in different places, but I still spent much of my time feeling like I was sleepwalking through life.

Something was missing.

Inevitably, whenever I’d meet someone new, our conversation would go something like this:

Them: “So what do you do?”
Me: “Well, I work with computers, but my real passion is writing.”
Them: “Oh really?  What kind of writing do you do?”
Me: “Er…I write a lot of emails and documentation and stuff.”

At which point their eyes would glaze over and they’d change the subject.

It wasn’t that I couldn’t write on the job.  Most people in the IT field are horrible to mediocre with written communication, and my talent afforded me many opportunities, from procedural manuals to training materials to heading up a department newsletter.  But at best, it was still just an IT job masquerading as a writing job.

I spent the better part of my IT career wishing I was doing something else.

I knew I could do so much more to help others using my gift, but the question was, “how?”  Technical writing was out of the question; I’d be bored to tears.  I had seen the inside of the newspaper business and found the politics of journalism intolerable.  I joined a short fiction workshop but had trouble thinking of it as more than a hobby; after all, how many short fiction writers can the average person name?

“The One”

After some exhaustive web- and soul-searching, I finally stumbled upon a book called The Well-Fed Writer by Peter Bowerman.  It was all about using your writing abilities to help businesses generate leads and customers through advertising and marketing.  In other words, copywriting.

As I read through the book, I began to realize that this was a field where I could conceivably find everything I was looking for in a career.  It was love at first sight.  I ran to introduce copywriting to my parents. I showed it off to all my friends.  My search was over.

The Honeymoon Phase (aka the Brain Vacation)

This is the point in a relationship that many refer to as the “honeymoon phase.”  It’s that time where everything feels perfect.  They can do no wrong in your eyes.  You want to spend every second together, and when you’re apart, you can’t stop thinking about them.

This is how it was when I started working on my copywriting business.  I immersed myself in every course, conversation, book, ebook, email, and blog post I could find on or related to copywriting.  I spent countless hours developing and revamping my website while attempting to apply all the “expert” advice on selling on the web.  I went to numerous networking and speaking events and started generating leads.

And as with a relationship, the real test begins when the rose-colored glasses come off and reality punches you in the face.  You begin to recognize the flaws.  You start to experience conflict.  It becomes clear that if you’re going to make a long-term commitment, it’s going to require real work.

Unfortunately, I was so sure of myself that reality had to beat the crap out of me before I began to accept that I was losing the battle.

Too Much of a Good Thing

In the process of trying to learn everything I could about copywriting, I had become an information hoarder.  This approach worked for me until I realized how much time I was spending on my business and how much I was neglecting the other important parts of my life: my marriage, my family, my friendships, my day job, my sanity.   I knew I had to pull back.

Now I was faced with a million things I could be doing to build my business, and instead of feeling empowered, I felt completely overwhelmed.  I didn’t know where to focus my attention and constantly second-guessed myself.  When I worked on learning the skill of copywriting, I felt like I was being a perfectionist and should be out looking for clients.  When I was out looking for clients I worried that my website wasn’t up to snuff.  When I worked on my website I thought it would be useless without a portfolio.  And how could I develop a portfolio without actually writing copy?

I reached the point of what my dad would refer to as “paralysis through analysis.”  I overthought things so much that I wasn’t getting anything constructive done.

Nice Guys Finish Last

Although I gave plenty of attention to my website, I had only a vague understanding of what I wanted to accomplish through copywriting: I wanted to use my writing ability to help the businesses I believed in accomplish their missions.  I came up with the tagline, “Copywriting that helps you help others,” figuring it encapsulated that purpose.  But I didn’t really know who I wanted to help; I just figured that by positioning myself as “helpful,” I’d attract helpful clients.

I followed all of the basic conventions of writing copy: emphasizing features over benefits, positioning myself as a problem solver, having a clear call to action, and so on.

I then launched my website and proceeded to gain exactly zero leads through it.

At this point, I resigned myself to the notion that my website wasn’t going to attract an audience on its own.  I would have to go out there, find people, and direct them to my website.  I attended various networking events, presented myself as a “helpful copywriter,” and in some cases even offered to do work pro bono in exchange for a reference or testimonial.  Some people jumped at the opportunity.  Many of them were just starting out in their own businesses, and sometimes I’d have to explain to them what a copywriter was, but once they understood and realized what I could do for them, they were all for it.

Unfortunately, at some point along the way, each project would get derailed.  Sometimes my clients would decide they weren’t ready to market themselves.  Others would start the process and then drag their feet or back out somewhere along the way.  As a result, I wound up with a bunch of unfinished projects, a barren portfolio, and a growing sense of disappointment and despair.

Relationship Counseling

At this point, I felt like I had two choices.
I could either give up and resign myself to a dispassionate life fueled by dispassionate work, or I could seek help.

I decided to seek help.

I had chatted with different experts in the field at different times, and while they all had a lot to offer, there was one person in particular who stood out: Johnny B. Truant.  Although he wasn’t technically a copywriter, his main vehicle for developing a fan base was his writing.  I loved reading what he had to say, and every product or service he offered I either purchased or at least felt would be a good investment if I hadn’t already overloaded myself with information.  I reached out to him about coaching, and once we determined it was a good fit, I hired him.

Johnny has been a huge help in a number of ways, but when we first started, he gave me one simple piece of advice that truly changed the course my business.

He recommended that I start by focusing on the “About Me” page of my website, and particularly on what I do and don’t want in a client.

Suddenly I was able to see all of  my failures in a new light.

By trying to learn and do everything at once, I wasn’t getting anything done.  The suggestion to not just start with my website, but specifically with my About Me page, gave me one manageable task to focus on.  Not only was my paralysis gone, but I was starting with the most familiar part of my business: me.

Almost right away, I realized that my tagline, “Copywriting that helps you help others,” was problematic.  It begged the question “what does ‘help others’ really mean?”  And it was a question even I didn’t know how to answer.

However, after digging deep, I realized that when it came to helping others, what got me most fired up was persuading them to try new things.  I had seen how much trying new things had changed my life for the better and how much it enriched other people’s lives, and I wanted to extend my reach by helping businesses that shared my mission.

I was then able to identify the specific kinds of companies I wanted to work with because they were the same ones I gravitated to in my personal life.  And thanks to my past disappointments in prospecting, I had a better idea of where NOT to channel my efforts.  It dawned on me that if someone’s business wasn’t well-established, if they weren’t serious about connecting with their target market, or if I had to sit down and explain to them what a copywriter was, I was setting myself up for disappointment.

Now, armed with the knowledge of who I was, what I wanted to do with my business, and who I wanted to work with, everything began to flow.  I was able to write my web copy and share my ideas from the heart instead of strictly by the book.  I knew specifically who I was talking to and where to find them.  And without having to plan ahead too much, I always knew what I wanted to do next.

Despite a lot of stumbling and a lot of heartache, I didn’t give up.  And as it turns out, copywriting was the perfect match for me.

Lessons Learned

1. Embrace your bad experiences.

No job, not matter how painful it may seem at the time, is a waste of time.   Each one affords you the opportunity to get a better sense of your strengths and weaknesses, your needs, and what you refuse to put up with.  You can use that knowledge to arm you for your next job interview, or, in the case of starting your own business, to help you create your ideal environment in your business.  If you learn that you like working with other people, you’ll know that sitting at your computer all day without any social interaction is going to burn you out, and look for ways to bring human contact into your work.

2. Take it slow.

Just because you’re passionate about something doesn’t mean you have to become consumed by it.  If you try to do too much at once, you’re almost certain to burn out eventually.  But if you focus on taking this new endeavor a step at a time and focus on the quality of the moment, you’ll build a solid foundation and be in a much better position for a long-term commitment.

3. Be yourself.

Trying to be what you think others want and impress them means you’re not being true to yourself.  The end result is that even if you do attract prospects, most of them won’t be a good match.  Instead, start by developing a very clear image of who you are and what you want to achieve through your business, then identify who your ideal candidates are and who’s likely to be a waste of time.  If you know what you want and project that confidence, you’ll be able to connect with the right people.

4. Ask for help if you need it.

If things aren’t going well, sometimes getting outside help is the best solution.  And just as with relationships, there isn’t one right coach for everyone.  Having good credentials is great, but make sure you find someone whose attitude and values are aligned with your own.  Once you find someone you “click” with, they’ll be able to guide you in the right direction while still giving you the freedom to do things “your” way.

Have you tried to start or considered starting a business of your own?  What’s worked for you and what’s stood in your way?  What would you do differently if you could do it over again?

Post your comments below.


  1. Hi Brad – I really enjoyed this post! I became aware some years ago that I have an attention span of 3 -4 years when it comes to projects. I was on a PTA committee for five years – during the first three I was full of enthusiasm, by the fourth I was getting bored and in the fifth year I was crawling up the wall and hating schools. This happened again with my fling with theatre and by the Society for the Arts I knew to resign from the committee by the end of the fourth year.
    At school I was not expected to stick to anything, finish what I started or arrive on time. Now that I know it is not a character defect I can embrace new things – take from them what I need and keep moving towards what I really want. Life is miraculous and too short to be living in quiet desperation!

    • Brad Jorgensen says:

      Hi, Sara.

      Although it’s important to recognize when something isn’t working and move on, trying new things doesn’t have to mean a full-fledged “break-up.” Sometimes when you hit a wall, all it takes is a subtle change or a little more variety to reinvigorate you. I know if the scope of my copywriting services was limited to websites, I’d lose my mind. I imagine if your artistic expression was limited to watercolor paintings (which are amazing, by the way) or your only subject was a particular tree, you’d get stir crazy. That’s probably why you explore other formats, right?

      I think it’s easier to stay committed when what you’re doing is aligned with both your desires and who you are. Maybe you believe in the arts but don’t like the committee dynamic and prefer more autonomy. Maybe you would have enjoyed school more if you had been given more freedom to think outside the box. I’m just speculating, of course.

      I hope you find “the One” someday and will discover that you’re able to make that long-term commitment while still finding ways to keep it fresh.

  2. I am happy to read that you found your way to happpiness. It sure shows in your photo and comes across in your words. I remember you really struggled with the paralysis you mentioned. I knew you would be a great success in whatever you ended up doing. You’re just an awesome person.

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