The 26 Character Blog

The 26 Character Blog


Helping you train and run your content marathon.

What Happened 365 Days Later?

One year ago, I wrote this post, where I officially announced 26 Characters.

What’s it been like? It reminded me of becoming a father. Why? You’re not really sure what you’re doing, but you figure it out through trial and error. Or, other people help you.

Has it been everything I thought? Yes and no. Some things were a breeze — after all, I’ve been in marketing for 20+ years.

What’s been the most fun? I’ve loved developing my brand, building my website, and helping companies with their strategy and content creation.

But many things were new, like building solid infrastructure, creating contracts, and finding customers. Of course, getting customers is the hardest; the amount of effort varies considerably. Sometimes, it’s ridiculously easy — I’ve had clients come in through casual phone calls. Others took forever (and others are still taking forever).

Even with all the ups and downs, I’ve had a good first year. I’ve worked with some great companies.

So, what are my biggest takeaways? Here are the key things I’ve learned:

1. Getting to “yes” or “no” is great — everything else sucks.

To no surprise, the number one thing you’re focused on is sales. It’s all about getting to yes or no. Of course, it’s fun getting to “yes," but I don’t mind hearing “no." Why? You get clarity.

What’s worse than “no?" When you don’t hear anything. Why don’t some people say “no?" They don’t want to offend you. Or they need more time to make a decision. You might be thinking, why don’t you just ignore these people? Here’s the catch: some come back and say yes. Even when you think they’re a no, they’ll come back and buy. Which, of course, makes it worth pursuing these people in the future.

2. People respond better when you talk about their challenges.

A book that’s had a big impact on me is The Brain Audit, by Sean D’Souza. It says buyers go through seven stages in order to buy something. The first is identifying with their problems. If you don’t start here, it’s hard to make a sale. Looking back, I was really bad at this. I assumed I knew the issues based on my research, or knowledge of their business. My big takeaway? You never know their real problem until you ask.

3. Working hard doesn’t mean anything.

It doesn’t matter how many hours you work, you’re eventually going to run out of time each day. Sure, you need to be a hard worker. But just because you’re working all the time doesn’t mean you're productive.

What’s more important? How you spend your time. The question I ask myself now is, “how much of my time today was productive,” or, “If I could do today over, what would I do differently?” Try asking yourself these questions every day for one to two weeks. You’ll quickly identify how to be more productive.

4. It’s all about knowing company culture.

What’s the most important thing I’ve learned in preparing for new client meetings? You’d think it would be researching who I’m meeting with, looking at their website, or reviewing their social media feed. While I do these things, they’re not as important as understanding their company culture.

But culture is tough to understand. Why? It’s not written down like company values. What’s the best way to understand a company's culture? Speak to former employees. Ask them what it’s like to work there. You’ll quickly find out what’s important. Why is this so critical? Once you understand the culture, you can better identify what they look for when working with others.

What are some cultures I’ve seen?

A) The “We’re an Institution” Culture: Everything revolves around legacy accomplishments and precedent. What’s important to these companies? Showing them you’ve worked with other big, important companies.

B) The Sales Culture: Everyone is constantly selling you. Not just on why their company is great, but the vacation they went on, the hip restaurant they went to last weekend, or even why their donut shop is the best in town. How do you gain respect and traction in this environment? Show them you know how to sell, too.

C) The Uber Professional Culture: Their clothes, language, and meeting protocol are built around formality, order, and looking polished. How do you better connect with these companies? Mirror their behavior. Why? If you’re not one of them, they may not work with you.

D) The Startup Culture: Casual and innovative, with a chip on their shoulder (in a good way). What’s important to them? You need to show them you’ve built things from scratch and can be nimble.

E) The “We Don’t Have a Culture” Culture: There’s no real driving cultural force here. Everyone just creates their own little pockets of culture to survive. How do you find your way? Focus on the two things every business needs — help them sell more or reduce expenses.

5. Do you know why asking questions is a good thing?

Getting people to slow down and think isn’t easy. One thing I’ve learned to get their attention is to ask questions. Why? It forces them to think. After all, once you see a question, the brain needs to exert more energy to solve the problem. For example, what’s your favorite color? Not hard to think of your favorite color, right?

When I realized the power of asking questions, I immediately updated my website. I changed my product pages. I even updated my navigation — Want to Learn? Need a Plan? Ready to Create? — and I’ve made similar changes to my capability overview presentation.

6. I’ve never been more hungry for knowledge.

In a strange way, it felt good when I realized I didn’t know a lot about a particular area. I was humbled by my lack of knowledge. What did I do? I bought a bunch of books and listened to a lot of podcasts. Now, I have an ongoing queue of what I want to read.

This ongoing thirst for knowledge wasn’t always there in my former corporate life. Sure, there was always a need for more technical knowledge, but once I had it, I moved on. The knowledge I’m after now is ongoing. It’s more about understanding human behavior, being persuasive, and scaling a business. Knowing that I have so much to learn has been refreshing.

7. Sunday night never felt so good.

Ever have that dreaded Sunday night feeling when you’re faced with the reality of going back to work? I’ve had this feeling for most of my career. But I haven’t felt this way since I started my business — Sunday nights have been great. I reflect on the fun I’ve had with my family and friends on the weekend, and I start getting excited about work. Will this last forever? I’m not sure. Am I’m going with it for now? Yes.

8. You need to slow down to speed up.

I’m 43 years old. Why did it take this long to understand the importance of taking care of myself when it comes to work-life balance? The answer lies in what happened after three months of starting my business. As you can imagine, I worked a lot of hours. I actually don’t know how many hours —I just worked all the time. If I wasn’t sleeping, or spending time with family or friends, I was working on my business. The excitement and adrenaline rush kept me going. But after that, I found myself not as productive. Even though my mind was pushing me full speed ahead, my body said, not so fast... we’re not ready. This is where I learned the importance of taking breaks, or changing my surroundings. Once I realized I needed to slow down, I became more productive.

9. I love not having an office downtown — until I really need one.

I’m writing this sentence at 5:43am in my home office. It’s dark outside. I hear a lot of crickets. My kids, wife, and dog (Ruby) are still sleeping. Ironically, Ruby used to wake me up in the morning. Now I wake her up. But I started writing this article somewhere else. I was on a park bench in downtown Chicago in between meetings. Why do I bring this up? Because for the most part, I choose where I want to work; I’ve never had this freedom before.

What’s the worst thing about not having an office? When I need a quiet place for a phone call, I can’t always find one. If I’m in the suburbs, the go-to spot is in my car. But if I’m downtown, I don’t have my car with me. There are a couple spots where I can find some peace and quiet. Where are they? I’m not sharing. Why? Out of fear that if more people find them, I’m totally screwed the next time I need to take a phone call.

And there you have it. Those are the key things I’ve learned in my first year.

Now, back to the post I wrote one year ago. If you remember, I told a story about how starting my own business felt like running my first marathon. So, where am I in my race?

Some days it feels like I’m running downhill with the wind at my back. Other days, it feels like I’m still at the starting line, asking myself, why the hell did I sign up for this marathon?

Of course, it was the challenge — of doing something new, seeing if I was good at it, and creating a business that helped companies solve a problem. And I’d do it again in a heartbeat.

See you out there on the streets!


Steve is the Founder & CEO of 26 Characters, a content marketing collective. Their hand-picked writers, photographers, designers and strategic brainiacs are among the 26 best in the business at showing and telling what you’re all about. Combine that with sensible pricing and a content menu where you can literally point to what you want, and you get 26 Characters – a better way to create content.

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