Jaime Derringer of Design Milk on 10 years of blogging, entrepreneurship & success

When she isn't orchestrating content for her various audiences, Jaime is a talented, self-taught artist who loves to explore shape and colour, using layering as a guide, to create the most beautiful abstract paintings – inspired by her study of the Japanese language, electronic music, sci-fi and architecture.

And if blogging and painting weren't enough to keep her busy, she loves to indulge in a bit of poetry, writing little verses whenever she can. She's also an avid runner.

But it wasn't always like this. Jaime started her career in a completely different direction. We caught up with Jaime to find out why, and to ask her what it takes to build a successful blog and business, the secrets of her success, and what she feels has changed since she launched Design Milk a decade ago.

Tell us how you got started? Where did you study, and what was your first job?

I don't have a design background, and I didn't study anything in school directly related to what I do now. However, I spent many years working on my high school and college literary magazines, so I have publishing experience of a very different kind! Post-college, I worked in the communications and marketing industries on print and online publications or projects, which helped me quite a bit. However, they were primarily in the medical sector—totally different from the kinds of things I'm writing about now!

You eventually left your job to pursue your blog and art full-time. Was it a giant leap? What was the motivation for doing so?

Yes, back in 2009, I left my' day job' to focus on Design Milk, and it was so scary. I think the final straw was when my boss told me she was getting a promotion and grooming me for her position. I may have winced, and I thought, 'I don't want your job—that sounds awful. How do I get out of this?'. That night I came home and told my husband that I was done and going to give my notice. It was risky, but we made sure we were in a position to take that risk financially and still be OK. I actually didn't really start taking my art seriously until about two years ago, but it's still a side project that I consider more of a hobby than anything else.

So Design Milk began in 2006? What was the inspiration behind the blog?

There was no initial inspiration. I had a great job that I enjoyed at that time, but we had a lot of downtime, and so while I was shopping for sofas for our new townhouse, I also discovered a thing called a 'blog'. I could use this 'blog' to share and save cool stuff I found online. I was using it as a kind of diary/bookmarking thing… I had no intention of it ever becoming more than that.

So when it started to attract attention, what challenges did you face in those early days of blogging?

Initially, I faced a learning curve. I didn't know a whole lot about blogging software, although I had taught myself some HTML and CSS previously, so I felt somewhat prepared for doing a lot of the site design work myself. That was certainly a struggle… nowadays, there are so many drag and drop features and plugins to assist in building a website – but back in the day, we were hand-coding everything!

However, I still face some of the same challenges that I faced back then. Not so much programming, but more along the lines of marketing, advertising, keeping readers interested, keeping up with social media, and being prepared to learn new things on the fly (we're just now experimenting with Periscope and Snapchat).

We want to be where everyone is, so that our content is always visible, and sometimes it's just hard to keep up with that every day. We're always anticipating where people will go to read content. At first it was RSS, then it became Facebook and now it's a combination of places from apps to Instagram… it's becoming more widespread and a lot harder to manage.

Ultimately, we're always struggling with how to reach the most readers and keep them interested in what we have to offer across multiple platforms while still trying to maintain the blog as the focus that feeds all these things.

It's been 10 years since you started Design Milk. What has changed in publishing during that time? For better? And for worse?

As I mentioned, it's so much easier now with the drag and drop platforms and the ease of creating a blog that's beautiful right from the start. We weren't ever able to take advantage of that… but we have been lucky enough to work with a great group of designers and programmers who help keep Design Milk running every day. So, I think the software has gotten better and easier for those who are starting out.

As for what's worse: there are so many more bloggers and so much more noise that it's hard to cut through everything and stand out. Initially it was easy, but now simply maintaining can be a struggle. It sometimes feels like we're running on a hamster wheel.

If others are considering starting their own blogs, what wisdom can you share to help them get off to a flying start?

My best piece of advice is to start a blog because you want to have a blog, not because you want to make money. Blogs will certainly help you if you have a side business such as an interior design company, or you sell products, but you really need to be committed to the blog otherwise, no one will continue to read it. I believe in consistent and quality content, something that's hard to keep up with, especially if you have another thing going on.

What tools and resources have you found to be invaluable in helping to build millions of readers on Design Milk?

Social media is the key to building a blog following, but you have to spend time on only the ones that are being used by your readers. There's no reason to spend hours on Snapchat or Pinterest if your readers are spending most of their time on Facebook. Pick a few platforms and put your energy into those instead of spreading yourself too thin.

What one secret can you share about Design Milk's success? Have you found anything to be especially helpful at attracting those readers?

People like to see beautiful images, and this has been great for growth. However, it's hard to keep readers. Therefore, I think the secret would be consistency. Always being present has been crucial to our growth.

Who has been your biggest influence and inspiration over the years? Why?

I have always admired Tina Roth Eisenberg of Swiss Miss. She's a powerhouse from her blog to her brand to her exploding ventures like Creative Mornings and Tattly. I am always waiting to see what she'll do next and cheering from the sidelines!

What's on your reading list? Any books you can recommend to creatives looking to succeed or get inspired?

I barely ever have time to read books, unfortunately! I've been trying to get through a Picasso biography at the moment.

You've had quite a varied career, even before you started your own blog and became an artist full-time. What skills and experience from your previous jobs have you found to be especially helpful in pursuing your creative passions? And why. Share some examples.

There wasn't anything incredibly creative about my previous jobs, however, I did learn a lot of great skills that have helped me along the way...

First up – how to talk and email professionally and handle myself in a professional matter. Not only does this earn people's respect, but it helped me hold myself out to be bigger and better than I actually was. I was one person running what appeared to be a magazine with a full staff. People were always surprised to learn it was just me in the beginning and that our team was still very small. Professional emails are also very important, especially when it comes to asking for things, developing partnerships and networking.

Next, working in teams and managing multiple projects. As a project manager, I was always juggling lots of projects and lots of people, too. I think that has helped me tremendously in gathering and managing a team that's all over the place. We don't have an office, so we do everything virtually.

Finally, being organised and getting comfortable with spreadsheets. Yes, spreadsheets. I can't ever seem to get away, but I've learned to love them! They keep me and everyone who works for me organised. There's a time and a place for a spreadsheet, though, so don't overburden your team with too many! Make sure you're on top of everything first, then distribute what's needed to the rest of the team. We're also now using Asana to manage tasks. It's great!

You've helped other businesses during your career with social media marketing – what have you found to be the best approach to building followers and engagement? Share some examples.

I mentioned it earlier, but I'm happy to repeat because it's so important: be present! Always be there, always be posting, always be in their feed. If you disappear for too long, you're literally out of sight, out of mind.

Share things that you think people will also want to share. Social media is about word-of-mouth and sharing, so think about your content and consider what's shareable and what they'd want to tell their friends about.

Freelancers are often time poor. What one thing would you encourage them to focus on in order to raise their profile and attract clients? Can you explain more or give any examples?

I'd first recommend that they create an online portfolio – something beautiful and engaging but not overdone. Something that works on your phone, iPad, and desktop. I think any creative who has a body of work needs an online presence that demonstrates their capabilities.

The next way is to make it easy for people to recommend you. Get a Facebook page, an easy URL to remember, memorable business cards. Make yourself stand out in some way or another. Design Milk is such an odd name with an even more curious logo, and I think that has undoubtedly helped our visibility.

Also, get out there in person. Face-to-face meetings and networking events are invaluable. I've created so many great relationships that way. It's old-fashioned, but it works!

What challenges are you hoping to overcome this year, if any?

I'm working on a few new projects requiring more of me this year – more learning and more experimenting. It's exciting! We will try some new (top secret!) things and see where they lead us. I'm hoping to get a better grasp on things like audio and video and more interactive content.

What does a typical workday look like to you? What's your morning routine?

Oh, it's very boring! I wake up and get my daughter off to daycare. Then, I spend the rest of my day sitting at the computer! I try and take small breaks throughout the day to rest my eyes and walk around. I usually go for a run or hit the gym for an hour at some point, but the time varies every day. I love getting my training over with in the morning, but I often have more energy in the afternoon.

After work, I eat dinner with my family and settle in for playtime, TV time, or art time. I draw and paint on the side. Most days are the same – I work best with a routine. It's not very glamorous, but I'd never get anything done if I was jet-setting all the time!

How do you stay productive?

After ten years, I still love what I do every day. I am almost always motivated to work. I think there's an element of responsibility and fear in there – that it's up to me every day to show up and work; otherwise, readers will not have anything to read, contributors won't have anything to do, and no one will get paid. Running your own business puts a lot more stress on you, but if you like the added pressure of being in charge and you get motivated by crossing things off your 'to-do' list, then entrepreneurship might be for you.

Another way that I keep myself motivated is when I hear all the great things that people have to say after being featured on our site. We've made great things happen through our editorial, from helping designers get jobs to connecting them with manufacturers, and the 'thank you' emails are what keeps us going every day.

So Dog Milk came next in 2010. Why did you branch out to pooches, and how has that been received?

Ha! Yes, Dog Milk was a labour of love that came out of the fact that there wasn't anything like it out there (and really still isn't), and that there was an overwhelming number of design-themed dog submissions sent to Design Milk. I discovered that there was a niche that I could fill, and so I did. It's still a very popular website in the dog-loving designer community and Capree Kimball, Dog Milk's Managing Editor, does an awesome job of keeping it going.

Adorn Milk is your latest venture, launched in 2015. How does e-commerce fare to running an online publishing platform?

I briefly operated a design-themed online store in 2008 called Vitamin D(esign). However, it was a monster and too much for me between inventory and shipping, a day job, and the blog, so I shut it down, even though it was successful. I was overwhelmed.

Fast forward to 2014, I started thinking about all the compliments I constantly receive about my jewellery when out and about. There aren't too many places online to purchase modern jewellery created by designers, architects and artists. Therefore, I started thinking about opening a small, highly-curated online shop for this kind of jewellery… the only pieces I would wear myself. I launched it in February of 2015, and the shop had a very successful year. It's still a side endeavour, and I do most of the work, but it's a passion project that is very important to me. We'll have to see where it goes!

Running a retail business is much different to running a blog, although its social media is still very much the same — stay in people's faces as much as possible. However, the day-to-day activities are different, which keeps me on my toes. Thank goodness for easy platforms like Shopify, which are a breath of fresh air after the messy, complicated software I used for my previous e-commerce shop.

What's next for you? Anything you're currently working on?

I am working on some fun projects for this year, but nothing is 100% final so I can't talk too much about them. But let's say they involve more audio and video content for the site. We're also always looking for new ways to distribute our content through special events, pop-ups, and platforms like Periscope. It feels like there is a lot of possibilities in our future, and I'm excited to see where things can go.

Finally, if you could give one piece of advice to aspiring creative business owners, what would it be?

Don't compromise yourself, who you are, or what you want to do. Do things with intent and integrity. Work very hard, but with passion and excitement. However, take work breaks, such as time for walks, to enjoy nature or to spend time with your family. It will be a struggle, and there is no such thing as work-life balance on a daily basis, but you can achieve it long-term, so don't give up hope.