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Jess Wolfe is Glad You're Here · Jun 26, 2025

Why not?

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Jessica Wolfe · Jess Wolfe is Glad You're Here

I’m an early adopter. I’ll rephrase: a skeptical early adopter. (I knew Vine was a fast train to nowhere.) But most of the time, I’m game to jump on board. I think when the Lord put me together, he blessed me with an usually large dose of FOMO. (Which, in case my mom is reading this, means Fear Of Missing Out.) Whatever it was: a new social app. A middle school party. A free sample at the grocery store?? I must partake! Or at least be offered, you know? That way I can really steep in the anxiety of making a decision, then say no, then regret the no, but ultimately be considered, so net win.

Which brings me to Substack. A place I consider to be the new Wordpress for ex-bloggers and a safe space for writers of all kinds. Something about it feels familiar, but also new. Like how we all made bread during Covid but now we’ve leveled up to sourdough because Instagram tells us we have to or we’re irrelevant to society. Which reminds me I need to feed my starter… Whenever I see the cool kids gather, I gotta check it out.

So here I am. Slipping into an old/new shoe of writing recklessly without abandon. (Meaning there will be typos.) I’ve got no shortage of thoughts and words to share, and I’m not disciplined enough to write the book I’ve talked about for the last 20 years. Plus I’m tired of typing LinkedIn posts that are consistently pushing the character limit and most people’s tolerance for an acceptable length of a social post. So why not? And there’s that phrase.

Why not. These two little words that grossly contradict my typical over-thinking approach to life have been somewhat of a theme in the last few years. I’ll elaborate. Because I can. Glad you’re here yet?

A little over two years ago, March of 2023 to be exact, I lost my job. Not because I wasn’t amazing at it, because listen, I really was. People said so. I had reached mastery in many ways after years of honing and grinding. Rather, it was because the agency never financially recovered after Covid and the CEO had enough. Essentially, we got the Carrie / Burger post-it note of “I’m sorry, I can’t. Don’t hate me,” and two days later the business was shuttered.

The minute I got the news, I jumped on a call with a dear dear friend and co-worker of said soon-to-be-dissolved business (👋 hi, Denise!). After many, many curse words and a few bouts of tears (mine, not hers), we said something to the effect of, “wanna make a go of it?” To which we agreed, why not? And so here we are. Over two years in, and along with another dear friend (👋 hi, Meg!), we’ve built a business that we’re so damn proud of. One that lets us take care of our families. It allows us to what we love in this ever-changing world of marketing and strategy and it feels prettyyy, pretttyyy good.

And yet there are days when I’m knee deep in QuickBooks asking myself, “WTH am I doing here?” Or, I find us staring at each other from our respective living rooms and saying, “can you believe we’re doing this?” The freedom of it is both terrifying and intoxicating. Having permission to ask questions I’ve never had the privilege of asking myself, only my clients. Let me tell you, the driver’s seat is wild in this car. And I’ve always had a bit of a lead foot.

The second big why not I’ve experienced in this past two years came by way of a women’s retreat that I attended last summer. For those who are also Catholic, you may have heard of the Cursillo movement. In short, someone typically invites you to go and you spend a weekend+ with other women (or men) learning about your faith and working on your relationship with God. I can tell you, with complete sincerity: this retreat changed my life. Coming out of this weekend I’ve not only met some of the most wonderful friends I’ve ever known, but I’ve also become almost a new, better version of myself. I’m far less anxious. I’m way more trusting and open to God’s will for me, not always just white-knuckle grip, steering myself into the lane I’m “supposed to be in” but whatever lane is open to me. It’s been the perfect complement to the previous why not of starting a business, keeping me grounded in the reality of life’s ebbs and flows.

In other true FOMO fashion, I started doing two podcasts in the past year. One with my work besties, and one with one of my Cursillo besties (👋 hi, Mel!). The two are very different in focus, but I’m trying to show up as my true self in both, and let the two worlds live harmoniously side by side. They’ve been the most wonderful creative outlets for me, and both started with that familiar question of “could we/should we?” and a spirited, why not?

Of course there are plenty of reasons why not in many of life’s circumstances. You know, like if something is illegal, immoral, would put my family or kids in danger, yada yada yada, then maybe err on not. But what I’ve learned in my early side of my 40’s is that I’ve got this beautiful mix of experience and wisdom, and the grace of God that have set me up to do things I would have never dreamed of in my 30’s. Definitely not in my 20’s. But in my 40’s? Life feels like this massive amusement park that I’ve been building. Ride by ride, stand by stand. Some rides broke down, some stands gave everyone food poisoning. But it’s my messy park and I’m proud of it. And then, every now and then, a new rollercoaster shows up. There’s no line. There’s a version of me (or maybe Brad Pitt, depends on the day) standing there, bright eyed and giddy with excitement, holding out a ticket. It could fall off the tracks, or… it could lead to a whole new park.

Do I take it?

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