Be Smart & Be Helpful: Success, Generosity, and the Business of People

The complete text from my WordCamp Minneapolis 2018 Keynote. I am honored to have been able to present this year on how the success of my business has been shaped by generosity.

There’s something inherently terrifying about being asked to stand up in front of a room and tell people how to do something.

You look out over a sea of faces and you wonder… am I really qualified to be doing this? Do I know what I’m talking about? Is someone in this room smarter than me? Shouldn’t they be up here? No matter how many times you get up here to speak, no matter how comfortable you are, you can’t really shake that feeling in the back of your head.

And I’ve definitely done it a lot. By now, I’ve spoken over 40 times at tech and design events, where I am often teaching a particular skill or philosophy to the audience. That’s intimidating on its own, but at least I have a fallback of doing research, finding other industry leaders who support my viewpoints, and pointing at their smart words on a screen alongside my own. Their words provide social validation and justification for what I’m saying. It’s like a credibility life-hack!

But that’s not what I’m doing here, because all of that stuff is what you are going to be hearing about for the rest of the weekend. No, I’m supposed to be up here being inspirational. I’m supposed to talk to you about how to replicate my success in the field of WordPress design and development. Success? Sure, I guess. I’m literally supposed to stand here and just… talk about myself to all of you. And that is honestly the worst.

Come to think of it, why IS that the worst? Why is that worse than getting up here and talking about ideas, or processes, or techniques? Why do so many of us hate to talk about ourselves? Probably because it sounds an awful lot like Self-Promotion. Maybe even worse: it sounds like Sales.

That word, “sales.” It makes creative, or technical people like us kind of uncomfortable, doesn’t it? It sounds so disingenuous, even a little slimy. What do you picture when you hear the word salesperson, anyway? What do you picture when you’re told to sell yourself? Many of us form a negative mental picture of a person we do not want to be. Often, we picture boastfulness at best, and manipulativeness at worst. And partly, that’s from experience.

I’ve been to my share of networking and business events, and I’ve met those people – you know the ones – who only seem to be there to get ahead, grease palms, and present their pitch or business card to as many people as they can force to listen. It’s this prototypical image of a salesman, the person who talks AT you rather than WITH you, that makes creative people shy away from the concept of selling, claiming to hate self-promotion. And this image tarnishes the entire concept of networking, because we assume it’s all about ourselves. What can other people do for us? How can we use other people to further our own careers? Perhaps we think that sales feels slimy and selfish because, with that attitude, it IS selfish.

But obviously, the most successful people I know are masters at selling. They are business owners and product developers, speakers and innovators, creating and shaping the software I use every day. They present at events and conferences, and everyone knows who they are. Many of these people are in the room right now, and you’ll be hearing from them later today and tomorrow. But one thing you’ll notice is that these people are not the ones who run around trying to tell everyone all about themselves. And, interestingly, they’re also not hidden away from the crowds, delivering grand words on stage and then retreating back to their VIP area.

They’re the ones sitting in an inviting circle in the courtyard telling stories. They’re the ones working patiently with a new developer, helping them debug a coding problem. They’re the ones answering strategic questions for a new business owner just getting their foot in the door. They’re the ones inviting you to dinner, or lunch, or coffee, sitting down with you, being genuinely interested in what you have to say and having a conversation. They’re the ones that genuinely want to know about you, what you’re good at, what you struggle with, what you’re looking for. They’re the ones going out of their way to mentor new talent, answer questions, and grow the next generation of successful entrepreneurs and empowered clients.

That’s not to say these people don’t care about winning clients or gaining business for themselves and their company, or that they have a naive view of the marketplace. Successful people do care about the bottom line, they care about business, and they understand that they need to be able to differentiate themselves from their competition. But they also know that selling isn’t always about “sales.”

The reason is simple. Business, at its core, is about People.

A sustainable business is built by fostering meaningful, genuine connections with people, and helping people succeed. These industry leaders have been able to achieve what they have because they are generous connectors, collaborators, and problem solvers. Yes, they are smart, but more importantly they are helpful.

To repurpose a popular saying:

Tell a person about yourself, and they’ll remember you for a day. Make a real connection and help a person solve their problem, and they’ll remember you for a lifetime.

Which is why it’s unfortunate that I still see so much fear of open collaboration in the broader creative community. We see companies, individuals, and agencies partner together to produce incredible work. But when it comes to really sharing knowledge with each other, we still put up walls between us and everyone else. We keep believing the notion that our fellow professionals are not our friends, but simply our competitors. We are scared that we have to guard what we know, to keep it to ourselves, because we believe that our skills are the only things that differentiate us from other professionals. Without our special knowledge, our trade secrets, what is to stop our clients from going to someone else?

I think everyone could stand to learn a few lessons from what we are doing here in the open source community. After all, for better or worse, open source has built an entire business ecosystem on top of of a codebase that is required to be free and open to everyone. How many people here can attribute their current level of professional success directly to the fact that the software we use was accessible to anyone and the community surrounding it was so willing to help us learn?

So what is is that distinguishes us if the product of our labor is freely available? Who are we if not our skills?

Here in the WordPress community, we know that we can be competitors without always being competitive. I’ve seen this play out at dozens of events, where CEOs of “opposing” companies sit down as friends to discuss technologies, business strategies, and processes. Now of course, these talented individuals are not only smart, they’re strategic. They’re certainly not hiding behind a walled garden, but neither are they giving it all away at the expense of their business. The goal is still acquiring customers or clients that will pay them for the products or services they offer. And yet, there is still so much they are willing to share. That’s because they understand that business is about more than just the product of our skills. Remember, business is about people, and successful businesses are built on generosity. On helping other people succeed.

I got involved with organizations like WordCamps, the AIGA, and Girl Develop It because I have a genuine desire to not only continue learning and bettering my own career, but to help other people do the same. I usually joke that speaking in front of a group has been great for my business because I can trick lots of people into thinking I’m smart and then they want to give me money, but there is actually a grain of truth to that. Years of showing up to events, volunteering, speaking, sharing, and helping has meant that my business is now almost exclusively driven by referrals through people I have met along the way, sometimes years later. I have to do almost no sales in the traditional sense, because my value has already been sold.

Now of course, I’ve had to put in the work. And there was a ton of work. I’ve been doing this for years, and in the beginning it was often a real grind. Writing, teaching, talking, showing up… it takes an enormous amount of effort, and I have had to learn to be strategic about how I spend my time. I have specifically curated the events at which I attend, organize, and speak. I’ve had to learn the value of my time and my skills, and gain some basic education in pricing, presentation, and communication.

I understand that continuing to learn is a crucial part of success, and that sharing that knowledge helps to position me as an expert in my field. After all, my field is continuously reinventing itself, and I need to keep up to date on technology, best practices, and a whole host of other fields tangential to my own in order to continue to offer a valuable service to my clients. And, on top of all of this, I have to actually deliver on the promises I make at a level that matches the things I talk about. This means I need to account for not only the skills I need to make it happen, but allowing myself the time and mental energy to do a good job on my work.

But I am still blown away by how much of an impact being strategic, smart and helpful has had on my business, and I believe it can do the same for yours as well.

So with that, what concrete wisdom can I pass on to you?

Be Smart


Your educational journey has very little to do with your formal education. Learn to love learning.
Read blogs, read news articles, read longform content, and also read some beautiful fiction. Take classes, attend events, watch tutorials, get better at your career. Practice, put in the 10,000 hours and continue to get better at your craft. But also experience life outside of work and let those experiences shape you into a better version of yourself. Take up a hobby that has nothing to do with what you do for a living. If you stare at a computer all day, make something with your hands. Bring those life lessons back into your profession.


Hear people’s stories and be mindful of their lessons. Find mentors, advisors, comrades-in-arms. Find the people ahead of you and listen to what they’ve done to get there. Get out of the tech bubble and find people who do something totally different than you.
Surround yourself with people who are better than you, with people who will push you to do more. Don’t be the smartest person in the room. Find people with different opinions, who will debate with you, who will challenge you to think about something in a whole new way. Assemble their knowledge and iterate on it in your own life.


You will fail many times. Some might be small failures, some might be huge. I would know, I’m extremely good at failing, I’ve had a lot of practice. And I always find a new way to do it. The point is, it’s going to happen. So take a risk. Be vulnerable. Be uncomfortable. Make mistakes, fall down, reflect, and then do it better next time. Failure is a space to learn, to grow, or at least to realize you definitely never want to do that again.

Be Helpful


Everyone has something they know that someone else doesn’t know, regardless of whether they are new or a seasoned expert. No matter if you are just starting on your journey, or you’re much farther along, you have knowledge to offer the world. The more you learn, the more you can teach others. And teaching is one of the most effective ways of learning, reinforcing, and mastering concepts.

Pay it forward

Remember the people that have helped you on the way to where you are, and try to be that person for someone else. You never know when a piece of advice, a helpful tip, or even a kind and encouraging word will make a major difference to someone else’s career or life. I would never be where I am without the people who helped me get there, and it’s important that I continue that cycle for the next person.

Be genuine

Help like you mean it. Be honest about what you do and don’t know, provide authentic feedback, and be enthusiastic about your contributions. Find an outlet for your knowledge that you are truly passionate about. Share value, not because you expect something in return, but because you believe it should be shared.

Be Strategic

Pass it on, don’t give it away

There will always be people who try to take advantage of generosity to try to get something for free that they should have paid for. With so many people asking to pick your brain over coffee, or get questions answered, or just get a moment of your time, how do you know where to draw the line? In general, I prefer to “pass it on” by sharing knowledge with my peers, rather than “give it away” to someone who should be a client. Whether this is mentoring someone coming up behind me in my field, or helping a colleague with a question or small request, I’m happy to give my time to the people who work alongside me.

Find your boundaries

The exception to the prior rule is at events like this, where I’ve pre-volunteered to share technical or creative knowledge with people outside my industry, and there is a clear boundary between my time here and my professional time. Maybe you prefer to take on a formal mentorship role, or hold office hours, or set aside a certain amount of time each week, or just answer questions via a certain platform. Whatever it is, the important thing is to find your boundary, and own it.

Take care of yourself

You can’t give anything from a well that’s empty, and you won’t find success if you don’t take time to recharge. When we are first bitten by the generosity bug, sometimes we can get swept away in how good it feels to be a helper. As a result, we find ourselves overcommitted, stretched far too thin, and our performance in all parts of our lives suffers as a result. Sometimes, the truest form of self care is simply being able to say “no.”

If you take away nothing else from this talk, remember this: We are all elevated when we exchange knowledge and build relationships, whether that’s with the people we do business with, with the people we meet at events like this, or even just the random people we strike up conversations with on the street.

If you make the choice to be smart, helpful, and strategic, then you will almost certainly be successful. And if we all decide to share these values, together, the world will be a more open, collaborative place.

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