Why You Should Stop Waiting for Someday (And, How to Live the Dream Now)

Have you heard of the painted picture exercise coined by Cameron Herold in his book, Double Double?

If not, the short explanation is that you plan out what you want your business and life to look like in three years from now and then you work backwards to make it happen. You include lots of details like how many employees you have and what you do to market your business and what bloggers are sharing your products with their readers.

I changed the exercise for myself by planning for one year out, because of how fast things change in this world. I doubt many of us could really plan for three years away and get it right. I do this exercise about once a year, and I use it as a guidepost for my decision making over the course of that year.

Because I find this exercise fun and enlightening, I had the members of Sunday Society (my membership program for creativepreneurs) write out their own painted pictures for July’s monthly challenge.

Within that challenge some of the members mapped out their dream day—how their perfect day would go from the moment they woke up (even how they woke up) to the time they went to sleep.

One of the Sunday Society members, Inese, decided to live her dream day one day last week and she reported to the group that it gave her a huge boost of energy.

That got me thinking about how so many of us sleepwalk through our lives, hoping that at some point we’ll reach our business goals and be able to have that dream life we’ve been fantasizing about.

But, what if you didn’t have to wait for someday?

What if you decided that one day in this upcoming week you were going to follow your perfect day itinerary? (This is the point where you stop reading and plan out your ideal day if you haven’t done it already.)

If you work a day job, this might mean that you have to live your dream day one day on the weekend. If you have young kids, this might mean that you have to hire a babysitter or drop your kids off with grandma for a chunk of the day. If you’ve grown to dislike your business, this might mean setting it aside for a day to do work that you’re passionate about.

Maybe your perfect day includes something that’s completely out of the question for now such as living and working in Positano, Italy when you currently live in Texas. You can’t include that part but you might be able to take a day trip to the beach to work or you might be able to do all of the things you’d do on that perfect day in Texas, including sipping a margarita at the end of the day on your back porch while doodling in your bullet journal.

The point is to get as close as possible.

Whatever you have to do to give yourself one day next week to live as if you’ve reached your dream life, do it.

You might be wondering what’s so special about this exercise—why you should give up a day’s worth of work or a day of lounging on the couch watching Gilmore Girls.

I’ll tell you why it’s important.

It’ll give you a boost of motivation.

If you give yourself a day to live your dream life, it’ll inspire you to work harder to achieve it.

Once you know what it would be like—what it feels like—it’ll be easier to give the middle finger to procrastination. When your alarm blares the next morning and you consider tossing your alarm clock across the room, you can think back to why you’re getting up early and what it’ll feel like when you reach your business goals.

The next time something awful happens like your website gets hacked or a troll on the internet tells you that you need to hire a stylist because you obviously don’t know how to dress yourself well (yes…both have happened to me), you’ll be less likely to give up, because you know why it’s worth it to keep going.

I didn’t realize it at the time, but years ago, I used to live out my ideal day when I was juggling a full-time job and building a business. About once every three months, I’d take a personal day and I’d spend that day living the dream—waking up without an alarm, working out at the gym across the street from my apartment, writing all day long with short breaks to brew tea and stretch my legs, and ending the day in my fiancé’s arms watching Grey’s Anatomy.

Those days kept me motivated when I woke up exhausted and wanted to stay cuddled under our down comforter instead of getting up at 5am to write for a couple hours before work.

It’s like giving yourself a breath of fresh air. You can see that pinpoint light at the end of the tunnel and realize you can get there.

You can tell how far away you really are.

Here’s the thing about your dream day: you don’t know how far you’ve got to go unless you try. You might realize that you’re much closer than you thought and that you can follow your ideal day itinerary once a week.

You might realize that parts of your ideal day are doable on an every day basis like ending the day with a bubble bath and a young adult fantasy novel or spending 20 minutes meditating before you start work.

Whenever I work with a new one-on-one consulting client, I have them fill out a questionnaire and one of the questions asks them to describe their perfect day. When we start working together, I often ask them how far away they are from achieving it. I also go through it to see if they can start incorporating some of it into their daily lives now.

I had one client who said that her ideal day would start by working on her novel which was actually doable if she got up a bit earlier. Now she starts every weekday by working on her novel. I had another client who wanted to take a walk on the beach each evening and because she lived 10 minutes from the beach, it was achievable right away.

Sometimes we don’t realize how much better we could be living until we give ourselves the chance.

Now, you might be on the opposite side of things where you realize that you’re really far away from living this dream life. That can be motivating, too. It can get you thinking about what you’re willing to sacrifice now to reach your goals in a couple years.

In order to get to my ideal day, I had to give up all luxuries to save money. For almost a year, my husband and I stopped eating out, stopped buying clothes, stopped getting coffee or tea on the way to work, stopped meeting up with friends for a $15 drink at a bar in NYC. We stopped doing anything that cost us money, so that when I left my day job, we’d have savings to fall back on.

At the time, it felt like we were giving up a lot but we both think it was 100% worth it.

If your dream is really far away, is there anything you could sacrifice now to get closer?

We all make choices every day that either gets us closer or further away from the life we crave to live. What choices will you make today?

You’ll see if this is really the dream or if you’ve romanticized something that you don’t actually enjoy.

Sometimes we glamorize something that becomes a let down in real life. Maybe you thought you’d want to work from home by yourself but realize that it feels too lonely or maybe you thought you wanted to sell handmade jewelry for a living but realize that you become bored when you spend an entire day on it.

Maybe you have a reality check when you figure out that in order to live this ideal life you’d have to send your kids to a daycare or hire a nanny and that’s not something you want to do. Or, maybe you figure out that you have to be willing to network with other creativepreneurs and the thought of reaching out to other girl bosses makes your armpits start to sweat.

Almost always when I work with a creative entrepreneur who quits her day job, there is a tremendous struggle. Part of the time they can’t believe this is their life—that they get to do what they love day after day. And, part of the time they’re terrified or wondering if they made the right choice when they hit a bunch of bumps.

The grass always looks greener on the other side but is it really? In order to find out, you’ve got to give it a go.

I’m not naïve enough to think that spending one day in your dream world will make you realize you don’t want it. That’s why I also recommend that you live your ideal day as often as possible. Don’t do this just once—try doing it at least once a month (once a week is even better). That’s how you’ll figure out what you love and what you don’t.

You can make changes based on experience.

If you keep your head down and work hard without checking in with yourself on a regular basis, you might wind up creating a business and life that you don’t really love.

Maybe you realize that instead of working an extra hour in the evenings, you’d like to spend that time doing something fun with your kids like playing board games or going to get ice cream sundaes or reading Harry Potter.

Maybe you realize that pieces are missing—that you haven’t thought about the admin tasks and how they’d get done. You realize that you’ll need to include hiring an assistant and accountant in order to live more of these ideal days.

Regardless of whether you can start living most of your ideal life right now or if you can only include small pieces, remain aware of how you feel in the moment. It’s easier than most think to build a business and life that you end up resenting. If you continuously check in with yourself, you can make changes along the way and build the right business (and life) for yourself.

I’d love to know the CliffNotes version of your ideal day. What are some of the things that have to be included for it to be a dream day? Share in the comments below!

Want more information about Sunday Society, how you can join and work through these monthly challenges with a group of creative women? Click here.