Empowering Your Relationship with Money

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August 1st, 2012

The Summer of YOU! Dating Yourself

Last week, we invited you to take a Vacation with a Vision, or personal retreat, as art of the Summer of YOU! Your Own Happiness Project. This week, we’ve got another exercise designed to get you a little alone with yourself. Specifically, dating.

Dating yourself is one of the most fun and most difficult of our self-discovery exercises this summer. It’s fun because you get a chance to pay special attention to your own needs and desires. But it’s difficult because it’s just you and your date (which is also you). You’re not dating to treat someone else to a good time. You’re dating to give yourself the time you deserve to discover new things about what you are like, what you like to do and what you want.

Whereas a personal retreat has a very clear purpose in that it’s typically for exploring a topic in solitude or for recharging your batteries, a date with yourself is a little less clear, making it too easy to make dates with yourself to do what you do with yourself already. Like taking yourself shopping, or to get a pedicure or, even worse, to run a few errands.

These are NOT the kind of dates with yourself we’re talking about.

So, what is a date with yourself and why do it?

Imagine that you have the most thoughtful, curious and growth-focused partner in the world. All this partner is interested in is what you REALLY want to do, what you are like and, most importantly, in supporting you in becoming the person you want to be. In fact, he or she wants to know everything from what makes you laugh and cry to what truly inspires you. Even more, he or she wants you to experience new things and keep evolving as a human being.

Where would this partner take you on a date? What experiences does he or she want you to have? Where does he or she see that you’re holding back and what do they want to “push” you into exploring?

Dates with yourself are about becoming that thoughtful, curious and growth-focused partner to yourself. While fun is key, dates with yourself are primarily designed to take you beyond your comfort zone to new adventures that will allow you to experience and discover different parts of yourself.

This summer, we invite you to plan a weekly date with yourself. If you can’t squeeze that in, two dates per month, at the least. But remember, you’re doing this for the purpose of learning more about yourself so that, by the end of the summer, you can more consciously choose your true purpose for money and be more excited about investing (the final step in creating your Fearless Financial Foundation).

In other words, it’s FOR YOU and the time you spend with you will be well worth it. Here are a few tips for making dating yourself not only fun, but revealing:


  • Make Your Relationship Official: Plan your dates ahead of time (except for spontaneity dates – see below), and put them on your calendar just as you would if you were seeing someone new who you were excited about. While it’s easy to remember something you’re looking forward to, you don’t want to miss out on the self respect that comes with taking time with yourself seriously by actually scheduling it. 


  • Invite Pre-Date Jitters: A good way to tell if you are really stretching beyond your comfort zone is to gage your level nervousness about the date. Whether it’s because you’ve never done the date activity before, or because the idea of doing a particular thing scares the pants off you, fear is a sign that you might learn something new – so embrace it.


  • Plan for YOU, Not Someone Else: Get into the perspective the caring partner we discussed above and really think about what type of dates you need to go on. What would feed your soul? What do you want to learn? What would allow you to experiment with being the person you want to become right now? What do you need?


  • Leave Room for Spontaneity: Every so often make one of your dates spontaneous. Plan the time, but not the activity and get in your car, on your bike or on foot and go where the day or night takes you.


  • Stay Awake on the Date & Keep a Date Journal: Like all of our previous exercises, the idea here is to learn new things about yourself. So notice everything that comes up when you’re out with yourself and process it in your journal upon your return.


  • Keep the Purpose in Mind: You are looking for new insights into who you are, what you want and what you want to change, and putting yourself into new environments and situations is a great way to discover what’s next for you. Don’t forget why you are doing this so you can keep your dates fresh.

While the exercises we’ve suggested to this point have been primarily solo and introspective, dating yourself is a more public venture. That means you not only have a chance to observe yourself closely, but to observe others as well. What we see in others is sometimes a reflection of what is going on with us – so notice what you notice about other people, too.

Most of all, have fun and check in on your level of happiness (whatever happiness means to you) during your dates. After all, if you’re not good company or if you didn’t plan something enjoyable for yourself, you’re not likely to take yourself out again. Plan for success and you might find that dating yourself is something you want to continue to do for a long time to come.

To getting wiser!

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