What compassionate marketing and dating have in common

Lessons from seemingly parallel journeys

In reinventing my career (again!) and dating after divorce, I've been on a pair of deeply emotional journeys the last few years.

They may not overlap in an obvious way, but I've noticed a stunning amount of similarities in the lessons I've been learning and the healing I've experienced with myself, my clients, and other people in my life.

I shared these insights elsewhere last week. The response was so, so, beautifully, overwhelmingly positive that I wanted put these thoughts out there in a more coherent, intentional way.

First, a few words about my career to set the context.

I've been focused on my work with women-owned online businesses in the wellness and self-help space, helping them bring more magic and transformation to their customers’ lives in an expansive way that generates more revenue, joy, and satisfaction.

I get to do the most purposeful, joyful work of my life with people I adore. I feel incredibly grateful for how it's unfolded—and continues to.

Now, here's what I've learned about online business and dating along the way.

In copywriting, the goal of writing a sentence is to get someone to read the next sentence. That's it. You’re not trying to make a sale in the first sentence.

Likewise, the first date is to see if you want to have a second date. The second date is to see if you want to have a third date. And so on.

The first date isn't intended to set off your soulmate meter.

Understanding that helps clear the path forward.

That may not come naturally to you, particularly if you’re used to feeling a lot of pressure and stress around your business or dating life.

Everything works better when you can take the pressure off, which you do by not making the goals of each step be so damn big.

That doesn’t mean abandoning your big goals!

You can keep dreaming about your big goals while letting the individual steps be smaller, gentler, and kinder to you.

Another way to relieve pressure is by beginning to let yourself see how big the market actually is compared to what you need.

Yes, yes, I know, the dating market can be brutal. (God knows, I know!)

But you're not alone in it. There are a lot of good people like you out there, and many have similar ideas about what they want.

Just as a wonderful little online business doesn't need to find a million clients, if you're dating to find a partner, you don't need to find a million of them.

That may feel comforting to read, or maybe it doesn't, but sit with that.

You don't need to persuade hundreds of people to want to be your partner.

You're just looking for things to line up with ONE person. Just one!

It may not require hundreds more dates. It may not require dozens more dates.

People talk about dating being a numbers game. That's kind of true, but it also kind of isn't.

Think about your married friends—maybe even those who are so arrogantly sure that they have this dating thing figured out, because they found THEIR partner.

Online marketing secret: way more often than most marketers care to admit, we don't know what's going to work, or why what works does or what doesn't work doesn't.¹

Sometimes things happen for reasons you can't identify.

That's life, for better and worse.

There's freedom in acknowledging there are things you don't understand.

It takes the pressure off needing to figure everything out all the time. (Yay, anxiety break!)

It lets you be curious. (Not judgmental.)

That's where magic starts happening, because you can be curious not only about what you're observing but by how you feel.

You want a partner you feel comfortable around, right? Instead of focusing on the BIG GOAL of "is this my life partner?!" focus on how you feel in their presence. That’s a little step you can revisit time and again.

It helps you not overreact when an individual event doesn't go the way you hope.

"Oh no, this sales email didn't make any money! What did we do wrong?!" We sent it to 30 people. Only ten of them even opened the email.

It's okay. We can be disappointed or upset that we didn't meet our goal this time. We can see if there's something to learn here and tweak for next time.

But we don't need to toss the whole plan in the garbage.

There's not always a major, sweeping lesson. Even if it doesn’t go the way you hoped, it doesn’t mean something is seriously broken.

If you're deep on the therapy/self-help journey like me (hiiii!!!), you may be used to looking at experiences as an opportunity for learning or healing.

"What broken part of me explains why this person didn't want to date me?" you may ask yourself, consciously or otherwise.

As an aside, I used to work as a basketball scout—God, I've had a weird career—and something I learned from a mentor and always tried to remember is that you never know what's going on with someone.

That player you expected to be good had a bad game?

Maybe their mom's sick. Maybe their partner broke up with them. Maybe their little brother got beat up at school that morning.

If someone chooses not to buy from your business or date you, it's not necessarily about you. You don't know.

That doesn't mean it's about casting as wide a net as possible, or hustling and hustling and hustling to reach as many potential clients or potential romantic partners as you can. (It took me a while to learn that in both realms.)

That's how you get burnt out and lose your peace, especially if you listen to what "the experts" are saying.

Many clients I've worked with think, "So-and-so is on TikTok, and this person's on YouTube, and this other business has a podcast, and this person I follow has a blog. I need to be doing all these things in order to be successful!!!"

I try to support my clients in guiding them gracefully to the aligned path for them and their business. That means the RIGHT thing, not EVERY thing.

When you try to be everywhere, the only thing you ensure is that you won't have the capacity to be your best (or most authentic). And isn't that the version of you that you want your prospective customer or future partner to meet?

Let things be easy for you so that you can be your best and enjoy the process as much as possible. (Shoutout to my brilliant friend Jamie Varon for drilling this message home.)

When you're able to be in a place of curiosity and peace, you can think more clearly about what you're offering.

Yes, offering.

I don't want to call it selling. That can imply persuading someone to buy something that's not good for them. That's not what we're doing here. ²

Your peace is too valuable to try to persuade the wrong person to buy from you.

And your product or service—or you, as a human, looking for a romantic partner? You're worth too much to have to resort to trickery.

Your business doesn't need to sell to EVERYONE.

And if you're looking for a romantic partner, you don't need to find dozens of them—you want ONE. The right one.

It's always better to be genuinely not for someone than to be inauthentically for someone.

So what DO you have to offer?

Well, for starters, what do you WANT to offer?

What fills you with joy? (Again, how can this be easy?)

It's not worth bending yourself to fit into a space you don't want to be in anyway.

People who have their shit together are picky about what they allow into their lives.

If someone wants to hire you and your business, it's because they feel like you're the right choice. In one way or another, you're the best one for them.

But the more bells and whistles you add, the more you risk distracting people from the best things about you and what you're offering.

There's so much noise out there online. You have to be clear about who you are and what you're most dedicated to.

Dating is similar. Focus on what's important to you.

Don't pretend you're dedicated to things that you're not.

If you're not that into hiking—and as an Oregonian, I know this is blasphemy, but I'm not that into hiking—let the people for whom hiking is an essential partner activity pass you by. They can go date the people who love hiking. That leaves more non-hikers for you!

When you say no to what you don't want, you're creating the space to say yes to what you do.

Being memorable is important for both marketing and dating.

I don't mean in an attention-seeking way.

But when you know what you have to offer—even and especially when it's explicitly not for everyone—you stand out more and more to the people you ARE right for.

You can be a one-of-one candle casting a radiant flame that attracts the right people, or you can be a mass-market floodlight providing boring illumination.

It's okay that there are fewer people standing around the candle.

Again, you don't need everyone.

Think about someone being described as "nice," which is at best a yellow flag, if not a red one.

If it's one of the first words that comes up, it implies a lack of more specific, encouraging descriptors.

If "nice" arises before you get to "funny," or "compassionate," or "thoughtful," or "generous," or "a good listener," or any number of more specific words, you may have a problem.

There’s a reason that "Women won't give compassionate men who are intentional about making plans and who are good listeners a chance" is a sentence no one says.

I want to go back to the not taking things personally for a minute, because this really matters.

I don't know a magic hack for self-worth. I cried many tears working with difficult clients and dating people who made me feel broken on my way finding a shape of myself that I love.

Still, I know this:

When you repeatedly cut corners off yourself to try to fit with people who aren't right for you, eventually you find yourself looking down sadly at all the pieces of you scattered on the ground.

So, what do you do when things aren't working the way you want, instead of taking it personally?

Let's talk for a minute about timing and gratitude.

It bugs me when the manifesting folks talk about trusting the timing of things and being grateful for where you are.

Not because they're wrong.

It lacks compassion and understanding to the point of being actively unhelpful.

Here's the reason I'm bringing up timing and gratitude, in regard to not yet having the outcome you want...

What if you weren't supposed to understand this right now?

I'm not saying don't take responsibility for things.

I'm not saying don't try to learn what you can where you are.

But can you open yourself up to the possibility that you don't have enough information right now to understand everything? And that it's not your fault that you don't?

In a marketing campaign, when the first email or two isn't meeting your expectations, yes, you want to try to understand why.

You might look at data like open rates, or user behavior on a sales page, or your pricing, and try to understand what's going on and how you might adjust things.

But you want to be open to the possibility that you might not be able to find a clear answer yet.

Don't rush to the wrong answer so that you don't have to feel anxious about not having an answer.

Whether you're drawing the wrong conclusions for your business or committing to the wrong romantic partner, false certainty can be more harmful than sitting in uncertainty.

And with dating, sometimes the—super annoying!!—answer to not having the outcome you want is, "You just haven't met your person yet."

OOF. Ugh!

But there's freedom in that, because it means you don't have to conclude that you're broken, or that you're doing a bad job, or that something's wrong with you.

Again, I'm not saying don't be curious. But don't be overly quick to conclude that there's a problem—and that it must be YOU.

Gratitude, combined with acknowledging the role that timing plays, helps with de-personalizing things.

There are many cool businesses that exist because things didn't go the way people hoped or expected.

Twitter—millennial and older readers, remember Twitter being good?—started as a weird internal offshoot prototype for a different project.

Sometimes you find magical new ways your product or service can help people when things don't work out the way you planned. Your business may grow in unexpected directions.

And if you struggle with not having met your person yet, think about all the cool things you've experienced at least in part because that's the case.

I find myself thinking about all the incredible women in my life now whom I dated and who are now the most amazing friends that I feel grateful for everyday. If I had the outcome I wanted years ago, these people wouldn't be here. I love them so very much.

And I've had a joyful container to find my way to my soul's work.

Was that my goal 2-3 years ago?

Honestly, no. It was not.

It’s better.

Leave room for it to go better than you imagined.

Back to one of the remaining big marketing pieces: who are you offering to?

In my marketing work, I've found it helpful to support my clients in going behind focusing on traditional notions of demographics.

They're relevant as a pattern, but if that's where you put your attention, you're missing an opportunity to focus on how someone feels, what they struggle with, what they need, and what's in their heart.

Feelings transcend demographics and appearance. People make decisions—purchasing or romantic—on feelings.

I love Lily Womble for how she talks about what she calls "essence-based preferences" in dating.

How does someone experience life? What matters to them? What do they love talking about for hours? What keeps them awake at night? What do they dream of getting to do?

You have to give a shit to think about this. It's WORK.

(Yes, ALL CAPS.)

Giving a shit takes work.

Showing up takes work.

But if you're running a business you believe in, or looking for someone to spend your life with, isn't it worth it?

1. When I start working with someone new, I’m intentional and clear about not believing that I’m coming in as an expert on their business. I don’t have all the answers. But I want to be a supportive person in working together to helping someone find the right answers for them.

2. Not that I have a problem with the idea of selling. I like selling!