A New Chapter

It’s been six months since I last wrote and published something in long form. Since last fall, I’ve been reflecting on what it would mean to recommit to a regular writing and publishing practice. That time and space made me realize how much writing fuels my creativity and brings order to the rest of my life. 

But this time, it has to be different.

I started regularly publishing in the Fall of 2015 and kept it up for 456 consecutive weeks. I’m proud of this streak and was reluctant to give it up, but at some point, you’re just going through the motions, and I didn’t like that.

Discipline is a good thing until you realize that you’ve been at something way too long without a more pure intent.

Some of that content was very good, sometimes not so much, but I kept at it because so many people were cheering me on.

“Keep going, you’re doing great work.”

“Your pieces are a key part of my Sunday ritual.”

I’m proud of the work I produced, but I can also do better than sitting down on a Saturday night to get something out for Sunday, and I did that more often than I’d like to admit.

I regularly write for myself, but I decided that if I’m going to publish that work again, it has to be with intention: knowing what I’m doing, why I’m doing it, and who it’s for. Writing with clarity and purpose is as essential to storytelling as it is to sales. That’s where the magic happens.

What brought me here?

About a month after I decided to take a break from writing, I was also given a career break. This pause gave me a chance to reevaluate my professional journey and reconnect with the core of what I really enjoy: frontline sales.

For the past few months, I’ve been training and selling alongside my good friend Jason Bay. Working alongside Jason, I’ve gained invaluable insights into what it’s like to be back in the trenches, doing the day-to-day work of selling.

This experience has been humbling and eye-opening. I was very successful in the field over several years, and I’ve done a really nice job of distilling the fundamentals of what makes top performing sellers so good. While getting back into the trenches has been a breath of fresh air in some regards, it’s also been a wake up call in others.

Here are just a few key lessons I’ve learned:

• The rhythms of frontline sales are unique and essential to master. Every industry has its own motion, and even with years decades of experience, it takes time to adapt.

• Tools and technology don’t usually work as seamlessly as they should. Using them daily has helped me to relate much better to the reps I coach because the roadblocks that prevent productivity are often created by the very tools that should be making us more productive.

• I didn’t previously appreciate how much nuance there is to each selling vertical. I purposely left the industry I grew up in, and that caused more issues for me than I realized as I tried to relate to sellers from other industries. I comprehend that now more than ever, and will definitely be digging into this concept in future issues of this newsletter.

Overall, this experience is undeniably making me a better coach, and I believe it will absolutely make me a better writer.

Before I move on, I can’t say enough about Jason’s leadership. He reminds me of my strengths while also showing me where I can grow. His emotional intelligence, combined with his deep understanding of the sales process, inspires me to be better—for my clients, the teams I train and coach with him at Outbound Squad, and eventually for myself as I pursue a frontline role.

Why am I doing this?

For years, I’ve written about sales and the lessons I’ve learned along the way. Many of you have shared how much you’ve gained from my perspective. With fresh experiences and renewed purpose, I believe I can offer even more.

This newsletter is my way of sharing real, actionable insights from the field. Whether you’re a sales rep seeking growth, a sales leader trying to support your team, or someone curious about the art of selling, my goal is to provide you with valuable takeaways rooted in experience.

I’m less interested in being the talking head you watch on LinkedIn or YouTube, and far more interested in provoking your thought around what you can do to be more successful in sales and in your life.

Who is this for?

• If you’re an established seller trying to grow your business, this newsletter is for you.

• If you lead a sales team, this newsletter will occasionally be specifically for you, but most times, it’ll provide a perspective that helps you empathize with your team from someone who has held both roles.

• If you’re new to sales and you wonder what you might be getting yourself into, this newsletter might be for you.

• If you know me casually and wonder what it is I do for a living, this newsletter might be worth reading every once in awhile.

• If you’re family and wonder why I don’t call or write more often, this newsletter might help explain why. 😉

Why should you look forward to it?

This isn’t just another newsletter about sales. It’s a resource designed to:

• Provide insights from someone actively working in sales and coaching others. I’m sitting in the hot seat, not an ivory tower. My friend Mike Weinberg said this to me in a conversation last summer, “You know, it’s a lot different when they’re firing live rounds in your direction.”

• Address the emotional and technical challenges of selling, which often intertwine with personal roadblocks.

• Offer a unique, relatable perspective that helps you grow both personally and professionally.

Sales isn’t just about techniques or tactics; it’s about the human experience. The best sellers I know excel because they’ve mastered life skills, not just selling skills. That’s where this newsletter is headed.

I’m here to dig success out of the dirt right alongside you, and what I love about the new delivery platform I’m using is that it’s designed to encourage interaction.

Leave comments. Hit reply and send me your thoughts directly. I’ll occasionally be using polls and other tools to take your collective pulse. I’m excited about so many things that I’ll be able to explore in new ways.

When can you expect it?

Weekly(ish).

When I thought about my cadence, I didn’t want to run into the same issues I mentioned above. I also know that sporadic work won’t work for consistency, and every other week isn’t often enough.

I want to dive deeper into certain topics (wait til next week), and those pieces often take a while to develop. Other times, I’ll have a small handful of things on my mind that I’ll want to put in front of you because I think they’re valuable and worth sharing.

I also want to share what I’m learning about AI and how I’m using it, as well as some of the other thought leadership that gives me pause to think more deeply.

So here’s where I’ll set your expectations. You’ll see me in your inbox most Sundays, but occasionally, I’ll take a week off. I want to bring you work I’m proud of and not force anything for the sake of a streak.

The more I write and reflect on this, the more I realize how excited I am to help you Rethink The Way You Sell, so you can sell more effectively, and with purpose.

Thanks for being here and reading this far. Let’s take on the real challenges together, one step at a time.

Cheers,

JB

PS- If you didn’t miss me over these past few months, or if you just don’t resonate with the vibe of this new direction, please unsubscribe below. I’ll miss you, but I understand.