Listen to the phrase, “Once upon a time…”
What are you waiting for right now? What jumps into your mind? What thoughts do you have? What are your expectations?
How about this one?
It was a dark and stormy night…
When you hear phrases like those you might expect a fairy tale or a gothic story.
Expectations can be really handy things when you are writing an eNewsletter. You can either meet the expectations, so your readers are comfortable (like slipping into an old comfy pair of sweats) or you can shatter those expectations causing your readers to sit up and take notice (like putting on a new metallic suit). Either way, you are touching and connecting with your readers.
Let me show you what I mean. Once upon a time on a dark and stormy night…
Ok it wasn’t really a dark and stormy night and this is no fairytale. My wife Teresa was away for the weekend and I was taking care of my three kids by myself. I got a call from my neighbor Shannon saying that she thought that her dog had killed a squirrel in her three-year-old daughter’s room.
You read that right. A squirrel was living in their attic. Shannon opened up the attic and the squirrel ran down the ladder and into her daughter’s room, chased by her dog Diego. Shannon was wondering if I could come over and collect the dead squirrel.
I grabbed my gloves, put my son in charge of his sisters (which could probably be its own story about expectations), and headed to Shannon’s house.
Shannon explained that she thought that the squirrel was in the closet behind some stacked pictures. I started pulling the pictures away so I could bag the dead squirrel.
Did you know squirrels can jump really, really high? I found that out when the very live squirrel jumped at my face. I also found out that my heart can fit in my throat. I have never been so startled in my entire life. I screamed like a little girl and jumped back.
The squirrel went flying toward the closed window. If I had thought to open it, the ordeal would have been over. Instead, the squirrel bounced off the window and ran under the dresser.
So there I was, standing with a pillow case, chasing a squirrel around a 10×10 foot room. And that squirrel was fast. I chased it up on the bed and tried to get it to jump out the now-open window. The squirrel wasn’t buying what I was selling.
After about 15 minutes of this ridiculous dance and two near heart attacks, I cornered the varmint and pounced. I missed. But the squirrel didn’t. It bit me in the hand. Fortunately, its teeth latched into my glove, missing my finger by a hair. So there I was with a squirrel hanging from my hand. I threw open the door, ran downstairs, and launched it into the backyard.
It lay there stunned, then got up and ran off across the yard. I was left with a serious squirrel complex.
In this newsletter article, I set up and broke some expectations. First, I wrote about a squirrel. That’s a bit unexpected in a newsletter. Second, I led you to believe the squirrel was dead, then out popped a live squirrel.
When you are telling a story in your newsletter you need to be aware of the expectations of your reader. How do you decide? Ask yourself these questions:
- Are your readers going to respond well to a shock? My readers are adventurous and like a little risk in their personal and business life. But maybe you are in a very conservative industry like financial planning or law with very distinct best practices. You don’t want to break those expectations even in your newsletter.
- Is the acknowledged wisdom right? Sometimes a “Once Upon a Time” beginning is a great start to an article because it lets people know exactly what you are doing. You don’t want to break expectations by communicating something that is not true. But maybe the acknowledged wisdom doesn’t make sense. That is a great time to reverse expectations.
- Does breaking expectations or keeping expectations best communicate your main point? I like taking my real-life experiences and relating them to eNewsletters. But the point is to communicate information, not just tell a story. Make sure that you manage expectations so that your one point is communicated.
Bottom line, you need to decide if you want to meet expectations or delve into the unexpected. In the end, the way you manage expectations will determine the effectiveness of your newsletter.
Email is dead…email is dead!
So go the doomsayers crying out around the internet town square.
They are flat out wrong.
Gail Goodmen writing for Entrepreneur online, recently wrote an article debunking three misconceptions about the social media vs. email debate. The three she covers are:
- The Inbox is Irrelevant
- Social Media has Replaced Email Marketing
- Young People Don’t Use Email
Email is an established and tested communication medium. Every social network uses email to communicate with members including LinkedIn and Facebook. I use these services and I blog (no duh?), but I would never give up my email marketing. It is the basis for every marketing strategy I use.
More importantly for the busy professional, email marketing simply takes less time than social media marketing or blogs. Time is one of the most precious commodities we have as business owners. An eNewsletter pushes your message out to the people you have a relationship with and builds relationships. It doesn’t cost much, the investment of time is minimal (1 day a month?) and it is incredibly profitable.
Email is strong and it’s the best foundation for any other marketing strategy.
Email marketing is even more profitable than previously reported. Every year, the Direct Marketing Association (DMA) estimates the value of marketing channels as an ROI. For the 2009, the estimated return for email marketing was $43.52. That means that the DMA estimates that for every dollar you spend on email marketing, you will get $43.52 back.
Chad White thinks that is a gross underestimate. Based on a study by Esilon that 67% of email subscribers buy an item from a physical (rather than online) store based on an email they received, Chad White concludes that the ROI for email is probably closer to $130.
That blows Search Engine Optimization, Blogs, and every other marketing channel away! Spend a buck (1 little George Washington) on email marketing and you are likely to receive $130 bucks in return.
And that doesn’t measure the value of the relationships you build with clients and non-clients as your write a regular, content based eNewsletter. As you provide answers to questions and insights that your readers need, you build loyalty that can’t be measured.
So what are you waiting for? Spend your buck today.
It all starts with an idea.
I mean that. Everything we do starts with an idea. The idea is the easy part. Then comes the execution.
Way back in 2004, I decided I wanted to climb all of the fourteen-thousand-foot mountains in Colorado. Easy to conceive, but hard to execute with three children and a busy work life.
In April, I set out on a gorgeous Friday to climb Mt. Bierstadt up near Denver, Colorado. It’s a relatively easy climb. This 14,060′ mountain is only about a 7-mile round trip with 2,850 feet of elevation gain.
By 14er standards, that is pretty easy. (Pikes Peak, for example, is about 26 miles round trip.)
But I forgot to take into account some difficulties. In April, the snow is not necessarily gone from the mountain ranges. In fact, it can be quite deep.

I also didn’t consider the construction on the Guanella Pass Road. They were closing the road every night and during certain times of the day.
So when I left my home at 3:00 a.m. on April 28, I had no idea what I had gotten myself into. I arrived at about 6:00 a.m. and found the road closed. I actually turned around to go home. Then I realized that it was supposed to be open according to the signs, so I just followed a construction truck into the area.
I got past the construction and drove toward the trailhead. But I could only get within three miles of the trailhead because of the snow. It was now 6:30 a.m. (an hour and a half later than my planned start time). Decision time; turn around and go home or strap on the snow shoes and give it a try? (Insert
Jeopardy music.) After some thought, I decided it was worth giving it a shot. I was completely by myself, blazing a path through virgin snow on my Cabela’s snowshoes.
Snow shoeing is miserable!
12 miles of snowshoeing is desperately miserable.
Turning around at 12,500 feet, not making the summit, and then having to hike back to your truck with a sense of failure and
exhaustion is desperately, horribly, exhaustingly miserable!
I didn’t make it. In fact, by the time I got home, a tendon in my foot swelled up and pressed on a nerve. I was in the second-worst pain I’ve ever experienced, and it lasted for three days. I couldn’t walk and I couldn’t sleep. That seemed a fitting end to my trip.

So I planned another trip to Bierstadt because that just wouldn’t do.
On July 3rd, I attempted the mountain again. But I changed a few things, correcting my mistakes. First, there is very little snow in July. I was able to drive straight to the trailhead. I left my house at 2:15 a.m. I also approached the mountain from the other side of the pass, avoiding the construction entirely. I reached the trailhead at 5:00 a.m. and set out.
By 6:00 a.m., I was as high as I had gotten in April. By 7:30 a.m., I was on the summit, the first person of the day. This was an entirely different experience. On the way down, I encountered at least 30 people who were also making their way to the summit.

But that difference is where we can learn a lesson about eNewsletters. eNewsletters start with an idea. An idea to help your business connect with new and repeat customers.
By marketing standards, a newsletter is pretty easy. But it still takes work.
We plan our newsletter, we design the layout, we think about topics, we develop a list, we launch the newsletter and the result is that we can’t walk for three days. In other words, sometimes an eNewsletter is just work. We work hard to connect and it is just a struggle that seems not really to work. You feel like a lonely soul struggling on snowshoes to make progress, and it is slow and painful and hard.
But if you want to execute your idea, the idea that got you started, you can’t give up. Because an electronic newsletter really is the least time-consuming, least costly, and most effective marketing tool available. Make a few changes. Try a different topic. Send your newsletter out at a different time. Change your format. Whatever you do, if you keep going back to the mountain, you will eventually connect with your target audience and things will get a lot easier.
And the crowds will follow. You will develop a connection with the people you are trying to reach and you will connect with like-minded folks who want the services you offer.
The mountain will still be a mountain, but it will seem a lot easier.
The bottom line is that the only failure you’ll experience with an eNewsletter is giving up. If it doesn’t work the first time, change a couple of things and try again. Make corrections. Experiment. But most important, keep trying.
Remember: The perfect is the enemy of the good. (Voltaire)
Recently, my son Mason and I were getting ready for a garage sale and we decided to sell our old motorcycle. The bike ran great, but we hadn’t used it in a while and we decided it just needed to go. Rather than sell the bike at the garage sale, we decided to list it on Craigslist in the hopes of getting a better offer.
We quickly received an offer from a man who lives a couple of miles away. He agreed to pay full price, but asked that we deliver the motorcycle. That posed a bit of a challenge. Because the motorcycle had not been licensed in a couple of years, we were not sure how to get it over to him. It wouldn’t fit in our van and we didn’t have a trailer that would work either.
In the end, we decided to just push it over.
So there we were, walking it along the street and a stranger came along and started laughing. He asked what were doing. We explained.
He said, “I used to be on the police force. No one is going to care if you ride that motorcycle a couple of miles.”
I thought that made sense, so I put Mason on the motorcycle. I kept walking because the motorcycle is not really designed for two people.
Problem solved.
We went a little further and one of Mason’s friends from school saw him on the bike. She asked him why in the world he was riding the motorcycle instead of me. She said that was SO DISRESPECTFUL (with rolling eyes like only a 5th grader can do).
So Mason jumped off and I jumped on to continue our trek.
Next thing you know, we got accosted by yet another neighbor. She looked at me and said, “I can’t believe you would let your son walk while you ride. What kind of father are you?”
(I kid you not.)
Now we didn’t know what to do. These people were actually watching us to see what we would do. I thought, “You know what, I’m not even keeping this stupid motorcycle. What do I care if the shocks are ruined?”
So Mason and I both jumped on the motorcycle.
We made it about 100 yards when Mason looked at me and said, “This is wrong, Dad.” He was right, so we stopped.
So there we were. We still had a half mile to go and no way to get the stupid bike there. We thought about it for a while and I came up with the stupidest solution ever. We picked up the bike and carried it between us.
After a quarter mile, Mason (who is only 10) started getting really tired. Which led to a bit of trouble.
Before we reached the new owner’s house, we had to cross a large drainage ditch. We got halfway across the bridge and the bike slipped from Mason’s hands. It slid right over the edge. I couldn’t hold on and the bike plummeted into the ditch, landing with a sickening crunch.
An older woman who was enjoying the spectacle commented, “That’ll teach you!”
None of the above actually happened, of course. Some of you will recognize this as a retelling of one of Aesop’s Fables, “The Man, the Boy, and the Donkey.”
So often when we are trying to launch an eNewsletter this is exactly how we operate.
We go to the internet and we look for advice. And there’s a lot of advice out there. We start with one idea. But that is contradicted by something else we read. But then we read another something else, and the first something else doesn’t make sense either.
What ends up happening is we drop the whole newsletter idea in the ditch and we never launch our newsletter.
Take the topic of the best day and time to deliver your eNewsletter. After a quick review of the available advice, you might conclude that
Tuesday or Wednesday is the best day and you should never publish on Monday or Friday. But don’t stop there. A little further research and you will find that
Friday and Wednesday are the best days. Yet another search will conclusively demonstrate that
Monday is the single best delivery day.
And off the bridge goes the motorcycle.
I’m not suggesting that you never get advice on how to improve your marketing, your website, or your newsletter (which is after all what I do.)
But I am suggesting that if you try to listen to every voice out there you will do nothing but destroy your momentum. Want to know the best day to send out your newsletter?
It’s the day you actually do it.
In the end, you want to decide on a plan and execute that plan no matter what anyone else says. If it doesn’t work, then you can tweak it. But if you don’t complete your plan of action, you will never get that far. Get all the advice you need, but then (in the words of the ubiquitous Nike) Just Do It!
Book reports have gotten a lot weirder since I was a kid. Back then, you read a book, answered some stupid questions and you were done.
Not so in the world of 21st Century education. Now book reports are extravaganzas.
My son is in the middle of one now. He has to read a non-fiction book, note five facts, define five words, and create a mobile that displays his answers in an interesting fashion. The entire mobile will be hung from the ceiling for “Night of Thousand Stars” at his school. (Never mind that there are not a thousand students at this school and that hanging a “book report” from the ceiling makes it impossible to see any of the details.)
My son is (to put it midly) disgusted with this assignment. He wants to play baseball, basketball or go hiking. He’s not interested in a book report mobile. He just wants the project to be DONE.
That desire has caused Mason to attempt a couple shortcuts. After reading a book about Michael Jordan, Mason’s first attempt at a fact was, “As a kid, Michael finally dunked the ball.” That was the entire fact. No details. No backstory. No explanation.
That just wouldn’t do. We insisted that Mason include some actual fact with his facts which led to the following scene:
Scene:
Mason, Chad and Teresa sitting around the kitchen table.
Mason (frustrated): “I can’t do facts!”
Chad (also frustrated): “Yes you can, Mason. You just need to add some details. It’s not that hard.”
Mason is now getting angry. He is not interested in facts. He just wants the assignment to be over.
Mason (very angry): “No, I can’t. I can’t do these facts. (Translation: I don’t want to do these facts. This is stupid.)”
Teresa (patient like only a mother can be): “You can do this Mason. Do you know the W-H questions?”
Without hesitation Mason responds: “What the Hell?”
Chad falls off his chair laughing, while Teresa tries to convince Mason not to talk that way (while trying not to laugh herself). Chad agrees with Teresa once he stops laughing.
Scene End
Mason sized up his audience and delivered a message that was on point and poignant. In the blink of an eye, he changed the entire dynamic of the conversation. My laughter broke the tension. He got back to work with a better attitude while I called my friends and told them this story.
A great newsletter can do the same thing for your business. It can turn strangers into fans and fans into loyal, raving lunatics who promote your business any time the conversation gets remotely close to what you do. To develop a great newsletter consider the W-H questions. Not Mason’s version, but Who, What, When, Where, Why, and How.
Here’s what I mean. Consider these questions as you plan your newsletter:
Who. Who are you writing to? Who is sending the newsletter? (You are, I assume. But do you sound like you when you write it?)
What. What is your audience interested in? What are you communicating? What should you write about?
When. When is the best time to send your newsletter?
Where. Where is the eNewsletter coming from? If your business is to make that place an appealing destination for your readers, can they picture it?
Why. Why are you sending it? Why should they read it?
How. How is your newsletter being delivered? How are you building a list?
Questions like these help you define your audience, determine your topics, and connect with your readers.
Asking great W-H questions helps you to create a great newsletter. Otherwise, the only thing you may hear from your
How do I build my list?
I hear this question all the time. And it makes sense. You have to have someone to send your eNewsletter to or there is no point. Right?
Nope! It’s is the wrong question.
As Seth Godin points out,
The problem with getting bigger is that getting bigger costs you. Not just in time and money, but in focus and standards and principles. Moving your way to the biggest part of the curve means appealing to an ever broader audience, becoming (by definition) more average.
More, more, more is rarely the mantra of a successful person.
The question you need to ask yourself is, “How do I build relationships with the people I do have on my list?” Building quality relationships with people must be the priority of your eNewsletter if you want it to successfully help your business. A large, unfocused, shotgun eNewsletter list won’t help you do that. You can’t just add people
Instead focus on building a quality list of people who love your voice.
When you first launch a newsletter build your list with everyone you know. Don’t just focus on “prospects.” Instead, you are trying to stir the pot of everyone you know. Often people who will never be your clients become your biggest fans and refer person after person to your eNewsletter and your business. Consider
- College roommates
- Long-lost cousins
- People from church
- Former clients
- Current clients
Anyone who passes the “I would talk to them in the supermarket” test should be included in your initial list (I borrowed this test from Michael Katz). If you could recognize someone in the supermarket and stop and have a conversation with them, then you should include them in your original launch list.
Once that is done, use the following three methods:
- Practice aggressive opt-in. Ask people you meet online and daily life if they would like to join your list. On a social network like Facebook or LinkedIn. Ask people if they want to receive your eNewsletter.
- Make your eNewsletter articles available for others to publish as long as they link to your site. Search Google for businesses that target the same audience you do and see if they accept articles. You’ll be surprised how often the answer is yes.
- Focus on providing excellent content. When you have great content, your existing list will offer the eNewsletter to others with similar interests. It’s organic and a referral will go a long way to breaking down skepticism.
The bottom line is you need to stop worrying so much about building a bigger list and focus on building a better eNewsletter. The relationships you build there will truly drive your success.
My five year old daughter Maia loves taking risks for the sake of adventure. I’ve yet to find something she won’t try.

Not my daughter...yet!
When she was two she would jump, flying through the air, into my arms at the pool.
In gymnastics, she is the crazy girl who runs full speed and leaps from the spring board with gleeful abandon.
When we went sledding a couple of weeks ago, she spun around on her sled by accident. She went flying down the hill backwards. Did she scream? Only in joy. She went off a jump backwards and laughed.
However, with every risk comes a certain potential for pain. Yesterday, my daughter while flying along on her scooter fell off and took a big ol’ chunk out of her hand.
So now, she is faced with a question.
Play it safe or keep living with risk in spite of the pain?
eNewsletters are no different. You can play it safe and boring and accomplish nothing or you can risk something different, interesting, exciting, or fun that will bring out the best in you and your readers.
(Can you tell which I believe in?)
Pick a voice and engage your readers. Don’t just play it safe and write in boring corporate speak. What you do is exciting. You better catch that excitement in your newsletter.
Remember what Goethe said, “The dangers of life are infinite, and among them is safety.”
Snow!
That’s right, it snowed here in Colorado Springs last week. And not just any snow, but blizzard snow. Blowing, cold, nasty snow in the last week of March.
But one person’s tragedy is another person’s opportunity.
At the beginning of the winter, I purchased a new sled for our family. We’ve has been waiting to try it out.
And waiting…And waiting. No snow. The waiting led to this question from our 10-year-old son, “Dad, when is it going to snoooowwwww!?” And again…and again…and again.
So when I saw that snow was coming, I was thrilled. Opportunity had arrived and we jumped at it. On Friday afteroon we were off to the park for some serious snow thrills.
Or so we thought. We didn’t take into account the wind. The wind blew the snow completely off the hills at the park where we sled. They were mostly bare. There were only two places we could sled in the whole park.
And the entire city was trying to slide down those two runs (or so it seemed).
We got in line and our kids got in a few good runs. They were enjoying themselves but the crowd was crazy and the wait was annoying.
One woman decided she was going to sit in the middle of the sled run to create a jump for her family. Then three boys ran right past us in line so they could race down the hill. Arrrgh! It was maddening.
But (repeat after me) one person’s tragedy is another person’s opportunity.
I looked around at all those empty hills and decided we would create our own snow hill. We moved snow from the bottom of the hill up the slope. We also made our own jump at the bottom of the hill that was about two feet high. It launched us right into a drift of snow that “cushioned” our landing (Although my sore back and twisted knee might disagree with that description).
It was a lot of work, but it was rewarding. Now we were having fun. No waiting, no crowd, just whoo-hoo!
Then an interesting thing started to happen.
The people who were looking for something different, something a little more adventurous, noticed us on our hill. We blazed a trail that others wanted to follow.
Our actions attracted the adventurous crowd. The three boys who had jumped in front of us came over. Another girl with a sled came over. “Can we get a turn?” (The answer was NO for the boys and yes the girl! Actions have consequences.) The number of people who came over was a small percentage of the whole, but they were ours. No other hill attracted the adventurous folks like the one we created.
It’s the same way with an eNewsletter. Sometimes the temptation to go along with the crowd is overwhelming. It’s easier to go where others have gone and it takes less work.
But the danger of that approach is that you get lost in the crowd. You don’t stand out. And when you don’t stand out, there is no reason to read your newsletter or use your services over someone else’s. Nothing sets you apart when you’re a follower.
But when you lead, magic happens. People follow you.
The way to lead with an eNewsletter is to infuse your newsletter with your unique point of view and your unique voice. Ask yourself these kinds of questions:
- What are you known for?
- What kind of experience do you deliver?
- What is the most important aspect about working with you or your company?
- What makes you different from your competition?
- What do your best customers say about you?
To stand out in a crowded email inbox and market, you need to offer something that appeals to your best customers and draws others with the same mindset like we drew those adventurous sledders.
I don’t know what your something is without talking to you. But you need to have a something. Marketing expert Seth Godin puts it this way, “What works is leading. Leading a (relatively) small group of people. Taking them somewhere they’d like to go. Connecting them to one another.”
Bottom Line: You need to be a leader, not a crowd follower, in your business. The answers to these questions will help you define your unique voice and perspective. Once you carry that over into your eNewsletter and your company, you’ll draw a devoted crowd of like-minded individuals. It may be only a percentage of the whole, but that small group is yours. No one can take them away from you.
Seth Godin raised an interesting point in his blog recently. It’s short, so I am going to quote it in full.
You won’t have any trouble at all finding someone who can tell you how to fit in.
They can tell you what to wear to that restaurant or this conference or that funeral. It’s not that difficult to figure out how to fit in. If fitting in is your goal, you should be sure to get great advice on how to do that.
Standing out, of course, is trickier. Stand out too much and you’re a jerk or a fool.
Clothing is not the point. You have this choice to make in everything you do, from your career to the words you use in a sales letter.
The point: choose.
Are you doing this to fit in or stand out?
It’s easy to fit in. You can use corporate speak or “wear the right clothes” so that everyone knows you fit. You can make your self sound like every other guide, trainer, bed and breakfast or professional service provider in your eNewsletter. You can hand out coupons for 10% off and pat yourself on the back for marketing your business.
The problem is, it won’t work.
As a small business owner the biggest advantage you have is that you can form unique real relationships with a small group of people that become your raving fans. You can’t create that unless there is something that makes you different, something that sets you apart from the mass of professionals out there.
So one of the first questions you have to ask yourself when you consider an email newsletter is, “What makes me unique?” Then you need to infuse that thing into your eNewsletter.