Welcome to the Design Your Dream Life series!
If you’re new here, this is a series where I am interviewing people who have designed their dream life. You can find all the interviews here on the Design Your Dream Life Page.
I am soo excited to have Holly and Greg with us today to share their story of designing their dream lives through their online business.
Holly and Greg are friends of mine, and I am so happy to see how they’ve grown their biz and become so successful online.
Here’s a a look at how they answered my questions!

Finish the sentence “I knew I was living my dream life when…”
I knew I was living my dream life when I realized I could work 1/10 as much as I do now and still live financially free.
Thanks to my career as a freelance writer and blogger, my income potential is unlimited right now. As a result, I am spending a ton of time working and socking away money so I won’t have to work as much in the future. It’s hard to think of another career option where I could determine my income based on how much I want to work. It also helps that, because I am a freelancer, I can work anywhere in the world. My husband and I travel around 3-4 months per year right now, and having that freedom is truly priceless.
What was your life like before all this that led you to make a change?
I spent many years working in a stressful position for around $40,000 per year. I wasn’t going to have the opportunity to move up in my career, so it was basically a dead-end job. I also worked 40-50 hours per week including weekends and holidays. To top it all off, I only had 15-20 PTO days per year and those had to cover vacation plus sick days and personal days.
I had no personal freedom and no time to enjoy myself. Did I mention I had small kids at the time? My life was exhausting and all I could do was work, keep up my home, and take care of my kids. I am so glad I took the plunge to explore new income opportunities because my old life really sucked.
What’s your lifestyle like?
While we’re location independent, I love having a home base. I’m not one of those people who wants to be a digital nomad or live out of a suitcase. I have two kids in school and want to provide them with a home. I also LOVE my house and enjoy being a homebody when I’m not traveling somewhere new.
I usually work a few weeks at a time then take a week or two off. Traveling frequently helps me avoid getting burnt out and it keeps my life exciting.

How many hours per week do you work?
When I’m home and not traveling, I can easily work up to 60 hours per week. It’s hard to “turn it off” sometimes when you can easily work as much as you want.
When I’m traveling, I usually scale it back and work only a few hours per day.
A few times per year, I will also take a few weeks completely off work. We have a three-week trip coming up in June and I am already planning to take two of those weeks off completely. It feels good to have that option, even if it means I may work longer hours later to make up for it.
How do you make money?
My husband and I started our blog in around 2011 and I started freelancing shortly after. I was able to quit my job to write full-time by April of 2013, and my husband joined me to blog full-time in February of 2015.
These days, I earn a little more than half of our income via freelancing and my husband earns the rest with our blog.
When it comes to blog income, it really varies where it’s earned. I would say that, on average, we earn 3/4 of our income from affiliate marketing and another 1/4 from my freelance writing courses, EarnMoreWriting.com and EarnMoreTravelWriting.com.
- Side note from Natalie- You can read how these three people are making $10k+ per month from Holly’s Earn More Writing Course.
I really like having as many income streams as possible, so we try to focus our time and efforts in several areas at one time. When you earn your entire living online, you can’t keep all your eggs in one basket.
How long did it take for you to make $1k per month?
It took us several years to earn $1,000 per month with our blog, but that’s partially because we didn’t really try to monetize at first. We didn’t really know what we were doing until around 2014 when we started experimenting with affiliate marketing and other revenue streams.
I definitely think people can earn money faster than we did, but I don’t regret the way we did it at all. Because we didn’t monetize right away, we were able to improve our writing skills and build a readership that actually cares what we’re up to. Sometimes I think people who monetize too quickly don’t do themselves any favors.
Blogging is about the long game if you want to make real money one day.

How long did it take for you to make six figures per year?
We didn’t make over $100,000 per year with our blog until 2017. In 2016, we barely missed the six-figure mark. So far in 2018, we are on track to have our best year with the blog and my freelance writing course.
As a freelancer, I was earning six figures within a few years of quitting my job. In 2016 and 2017, I earned over $225,000 via freelance writing alone.
One aspect of blogging and freelance writing I really love is the fact that you can truly earn as much as you want if you have the drive and the talent to succeed. There is no income ceiling and there are no limits.
If you can dream it, you can do it.
What do you wish you knew when you were starting out that you know now?
I wish I never listened to all the people who claim to be super successful!
When you go to blogging conferences or pay attention to Facebook too much, you get caught up in all these attention-seekers who want you to think they have the key to making money.
The reality is, the loudest people offering advice rarely have a clue what they’re doing. Most of the truly successful people are working quietly with their heads down, not up on a stage sharing their biggest secrets to success.
What advice would you give to someone who is starting out and wants to design her dream life?
I would say that you should never wait for someone to give you permission. I still remember when people thought we were crazy or silly for starting a blog back in 2011. They didn’t understand the point or what our goals were. We didn’t either really, but we still wanted to do something.
Sometimes all it takes is making that first step to do something that can change your life.
I’m so glad I never listened to the naysayers or the people who don’t have the courage to do what we did.
If you want to succeed at creating your dream life, don’t take advice from anyone who hasn’t done it themselves.
Most people are content with their 9-5 jobs and simple lives, and it scares them to dream big. Don’t let people with no vision scare you into settling for less than you deserve.
A Final Note!
I am so in LOVE with Holly’s story for several reasons. First, I love that she’s candid about how long it took her and how she’s super grateful for the journey (similar to me). Second, I love her advice about dreaming big – there are going to be people who don’t get it, but you shouldn’t let that stop you, even though it may make it harder. Still do it. You’re worth it.
THANK YOU to Holly and Greg for taking the time to do this interview and for sharing their personal stories. I’m so grateful for them!
Are you inspired by Holly and Greg?! Let them know in the comments!