Dana Obleman

Dana Obleman is the founder and CEO of Sleep Sense Publishing Inc., an education and training company dedicated to helping parents teach healthy sleep habits to their children. After becoming frustrated looking for easy-to-follow information online to help her with her own son’s sleep challenges, she launched Sleep Sense from the kitchen table of her two-bedroom apartment back in 2003. Since then, she has shown over 107,000 parents how to get their children sleeping through the night and has helped over 500 entrepreneurs launch fulfilling careers as Certified Sleep Sense Consultants.

“The secret to getting your baby to sleep through the night is actually the same as the secret to a successful business,” Ms. Obleman says. “Find a step-by-step system that has already been proven to work, and follow that system until you get the result you’re looking for. You have to expect a few challenges along the way, but if you have a clear path and a teacher you believe in showing you the way forward, I believe success will come your way.”

Dana has been featured on Good Morning America, CNN, WebMD, The Washington Post and Today’s Parent Magazine, among many others. She lives in Florida with her husband and 3 children.

Where did the idea for Sleep Sense come from?

I remember this like it was yesterday. My husband and I had struggled terribly to get our first son sleeping through the night. It was 2002 or 2003, so the early days of the internet. I kept going online and Googling “how to get baby to sleep” and getting so frustrated that all I could find was a bunch of conflicting information.

I have degrees in Education and Psychology, so I decided to dive into the world of baby sleep and figure it out for myself. After reading about a dozen of the most popular books on the subject, I came up with a system and — within just a few nights — our son was actually sleeping through the night!

I can’t tell you what a life-changer this was. The sleep deprivation (and resulting post-partum depression) had gotten so bad that I had pretty much decided I was NOT going to have any more children, even though I had always wanted a big family. As soon as our son was sleeping through the night, all those feelings disappeared and I felt like my old self again.

We were living in Canada at the time, where they give you a full year of maternity leave. I was about 4 months away from having to return to my previous job as an elementary school teacher, but I have to say I was not really looking forward to it. (The kids were great but the commute and staff politics were not my cup of tea!)

One day, my husband and I were walking around the park trying to brainstorm ideas for something I could do instead of going back to teaching, when he said, “You know, you’re so passionate now about babies and sleep, do you think people would pay you to help them? Almost like a personal trainer, but for baby sleep instead of exercise?”

A felt like a lightbulb had gone off inside my head! “Yes!” I said. And that is exactly what I decided to do, right then and there!

What does your typical day look like and how do you make it productive?

I’m not a morning person, so I usually wake up around 7:30 or 8. I spend at least a half hour journaling every morning, as that really helps me plan my day.

As far as being productive, I’ve managed to build a great team around me that takes care of all the parts of the business that I’m not good at. So I spend a good part of my day delegating stuff out to them and focusing on my “areas of excellence” which mostly revolve around helping my community of Certified Sleep Sense Consultants become more successful.

I also still LOVE to help parents with their babies’ sleep problems, and will connect with my customers any chance I get.

How do you bring ideas to life?

Well, I am very much an “ideas” girl, but I really struggle with thinking things all the way through. That’s why, for people like me, it’s so important to have a team that can help talk things out, brainstorm, and then make a plan. In other words, I bring ideas to life by telling other people what I want, and then letting them help me see how it can actually be done.

What’s one trend that excites you?

One of the greatest things about the Internet is that it has given so many people the freedom to create their own businesses. As a woman, I am particularly passionate about helping other women escape from jobs that do nothing to fulfill them by showing them that they CAN be their own bosses! You don’t need anyone’s permission, you just need some inspiration and someone who can show you how to get there!

What is one habit of yours that makes you more productive as an entrepreneur?

As I said before, I spend a lot of time journaling. I find that by writing things down first thing in the morning, I can set my intentions for the day so that when I get to the office, I know exactly what I need to do in order for the day to be considered a success.

What advice would you give your younger self?

Hire people sooner than you think you need them. I waited forever before hiring a person to do customer service and administrative tasks. I thought “Why would I pay someone else to do what I am perfectly capable of doing myself?”

As soon as I hired someone to take those tasks off my plate, I suddenly had a couple of extra hours a day to come up with ways to make our product better and keep our customers happier. Plus, I no longer had to spend 2 hours a day doing work I disliked! A total game changer for me.

Tell us something that’s true that almost nobody agrees with you on.

“Hard work is not a requirement for success.”

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I have three kids, all teenagers now, and I insist upon what I call “meaningful hugs.” I’ll hold them tight for a good ten or twenty seconds and just think about how much they mean to me. Do this with your kids — or whoever will let you — at every opportunity!

What is one strategy that has helped you grow your business?

Some businesses come and go based on fads and the tastes of the times, but some businesses are “evergreen.” If you can build a business in an evergreen space, you’re better positioned to weather the downturns.

People are always going be having babies, and those babies are always going to have trouble sleeping, which means there will always be food on my table!

What is one failure you had as an entrepreneur, and how did you overcome it?

Back in the early days of the business, I decided that it would be a great idea to set up a system where people could buy our product, The Sleep Sense Program, as a gift for others. Keep in mind, this was back when setting a system online for buying, sending, and redeeming gift cards was WAAAY more complicated than it is today.

We spent a ton of time and money building this idea out, and then launched it to absolute crickets. I mean, like, I think we maybe made 3 sales. Turns out people do not want to give a gift that says “You’re parenting incorrectly!”

As for how I overcame it? I just shrugged and moved on!

What is one business idea that you’re willing to give away to our readers?

Totally unrelated to babies or sleep, but why doesn’t someone invent a smoothie vending machine that makes smoothies out of fresh ingredients and put them in hotels. That way, I do not have to wait in a long line at the coffee shop first thing for a stale bagel!

What is the best $100 you recently spent? What and why?

Mani-pedi at my favorite salon. Part of my self care. I’ve been paying someone else to do my nails since LONG before I could afford it! Still feels like a luxury to this day!

What is one piece of software or a web service that helps you be productive?

Slack. I hate email and am impatient, so Slack lets me communicate with my team in real time without having to “compose” a thoughtful message.

What is the one book that you recommend our community should read and why?

A little book called ‘Anything You Want‘ by Derek Sivers. I would estimate I have purchased about a thousand copies of this book over the years to give away to clients and friends.

What is your favorite quote?

“If you have knowledge, let others light their candles in it.”

– Margaret Fuller

Key Learnings:

• Start your day by journaling. It clears out the cobwebs and sets you up for a productive day.
• Find easy-to-follow systems that have been proven to work in the past, and then follow those systems. Don’t reinvent the wheel.
• Starting and running a business should be mostly fun and fulfilling. Sure, there are always going to be parts of a business that you don’t enjoy, but there are usually ways to minimize your exposure to those parts of the business.