Once upon a time, there was a brown girl with twisty windy hair, and her name was Tara. Tara had no patience for board games. But she did like to play mind games and the real-life Game of Life with herself, against herself. (Eventually, she learned how to play it for herself.) And in the Game of Life she somehow aced school, got married when she was really young, had a kid, got divorced, and got married and divorced again. By the time she was single for the first time in her adult life, at 36, Tara had been married over 20 years of her lifetime!

So, she cooled her jets for awhile. It seemed prudent. It was prudent. She went to lots of therapy, changed a lot of her worldview, wrote a lot, prayed a lot, meditated a lot, walked a lot, danced a lot, sang a lot, played a lot. But at some point, Tara decided it was time to learn how to date. Remember, she’d actually never been on a real date to someone she didn’t marry, ever.

So, she made a game out of it. Tara downloaded a dating app, made a profile and proceeded to go on 3 dates per week for ten weeks. Rule #1: Go on 30 dates in ten weeks. Rule #2: Do not get married during this ten weeks.

Tara does not recommend you do this at home.

At the end of the ten weeks, Tara took her profile down. It was dang near a full-time job, this talking with and vetting of and seeing people, at this pace. And a couple of years later, she now finds dating to be growth-provoking and fun. She has not gotten married again yet, by design.

Tara (that’s me, FYI) also took away all sorts of lessons and insights and mind-changes from the experience:

Tara’s DIY Dating Challenge Takeaways:

1. There is someone out there for everyone. No seriously, everyone.
2. There are actually abundant people, and we’re mostly all wired for connection.
3. I do not have to be afraid of marrying everyone I date.
4. I do actually make good decisions regarding relationships, contrary to the story I was telling myself.
5. I am clearer now, for having met a lot of people, on what does and doesn’t work for me and how I want to feel around a person I choose to spend time with. I also know red flags and stay far, far away from them.
6. We all *think* we are clear on what we want in another person. But when we meet someone who is ‘perfect on paper,’ we may or may not be attracted to them. And other times, we might surprise ourselves at who we meet and really, really like.

In the end, I didn’t love the way most people treat online dating, almost like a job interview where you sit down, trade lists of qualifications and requirements with each other, and see whether the lists fit. It was too outcome oriented for me, too artificial.

But I also came away with a lot more ease and less anxiety about dating and relationships in general, which allowed her to feel more comfortable in the world in general. I ultimately focused on showing up in the world, all over the world, doing completely awesome stuff, and living an incredible life, as much as possible. And as a result, I started meeting lots more smart, engaged, caring gentlemen, all around the world, online and off. And then one day, a strange thing happened. Meeting people became fun. Learning about myself, in relationship to other people, and specifically in relationship to men, also became fun. 

This was just one of literally hundreds of Challenges I’ve issued to myself over the years. It probably started with health and fitness, way back in the day. My friend and I would meal prep in our little cottages, and we’d kind of challenge ourselves to eat clean all week, until cheat day. I did a Whole 30 that snowballed into a Whole 90. One time, my trainer issued—and I accepted—the challenge of doing 10,000 kettlebell swings in a month. Trust me when I say that my derrière has never been the same.

I guess before I go too far into why I find Challenges to be so shift-sparking and growth provoking, and the growth I’ve seen in my life in the course of taking on Challenges, we need to agree on some things. Or one thing. Namely, what I mean by “challenges”.  I’m not talking generically about things that are a little hard to do, or a lot hard, though I like them, too.

When I use the word challenges with a capital ‘C’ I’m talking about something very particular:

• A program of doing a certain activity (or, I suppose, not doing a certain activity)
• That I don’t currently do
• At a certain frequency
• For a certain number of days.

I think of Challenges as self-directed projects to change my behavior or spark some personal growth or development I’m clear that I’d like to have. Sometimes I want a mindset shift or want to make (or break) a habit, or I just have a sort of big project I want to sprint to finish, and Challenges are a container I’ve found that often works for me to get there.

And I mean they work in every area of my life. I’ve done a church search challenge, in which I attended a new church every week for a year (but I only made it 12 weeks before I fell in love with one). I did a very playful travel challenge of sorts, for my 40th birthday, to go to nine places in the world I’d never been in 18 months (though I made it in 12). This year, I wrote a book in 6 months, and I treated that as a challenge, too.

Right this moment I’m learning French on a self-imposed Challenge, I’m doing this Writing Challenge with ya’ll, and I’m in also doing a Vulnerability Challenge in the way I carry out the Writing Challenge.

Some Challenges I just take on, over time, as a part of my life. Travel is now that for me. I now take care to structure my career and my life in a way that allows for great swathes of time in which I can globe trot. But this goes for more specific, tactical behaviors, too. I have a one item in, one item out rule on buying new clothes and home goods, after issuing myself a Challenge along these lines, once upon a time.

Challenges perform the valuable function of holding the mental and spiritual space for a new habit, a new project or a breakthrough way of thinking or being.  They have rules or guidelines. They are voluntary, and finite in time. They are also fun, or I’ve learned how to make sure they stay fun, rather. If you do them right, they harness everything great about competition, with none of the nasty, perfectionistic aftertaste. And they build an incredible amount of momentum. They help you try on practices or

I cannot convey with words, not in this post anyway, the levels of interior and exterior and career and life and spiritual transformation I’ve experienced from issuing Challenges to myself, small and large. Since we’re all here, working on a Challenge together right now, I think I’ll make this a series, and share how Challenges have changed my life and why I think they are so powerful, in the next couple of posts.

P.S.: I issued a 30 Day Writing Challenge for Conscious Leaders a few weeks back, and over 150 brilliant souls signed up! I decided to take the Challenge right along with them, and it’s been a profound journey for many of us. Most people are journaling or free-writing every day, privately. But I wrote this post on Day 16 of the Challenge. I’ll be doing another writing Challenge in January; click here to get on the list for the January Challenge.