Artist & Entrepreneur Melissa Dinwiddie

Melissa Dinwiddie

Melissa Dinwiddie is a great example of someone with numerous creative passions who is actually making a full-time living from her art and online ventures.

But it’s not always been plain-sailing as her answers below reveal:

Please can you describe who you are and what you are up to at the moment?

Who I am and what I do has evolved quite a bit over time, but as I look back on my life, the one constant is a focus on creative pursuits.

I’ve made my living as an artist for many years but because I do so many different things, I now call myself a Multi-Passionate Creative ARTrepreneur and Creativity Enabler. I create in a variety of different expressions – art, music, writing – and I help other people follow their creative bliss through teaching, coaching and consulting. It took a long time to figure this out, though.

I blog about my creative journey and showcase my various offerings on my blog, Living A Creative Life.

As for what I’m up to, here’s a run-down:

I currently make most of my income from my art and design, primarily for weddings and lifecycle events, which you can find at I also teach calligraphy out of my home, and occasionally around the country, and I teach voice lessons and performance skills.

More recently I’ve been creating “digital products,” and I expect this part of my business to grow, and eventually overtake the wedding art.

In December I launched my first online course, the Thriving Artists Project *, which I created to help give other artists and creatives the inspiration and tools they need to bust the “starving artist” mindset and really thrive from their art. The TAP is an interactive membership site featuring interviews with successful artists and creatives, lessons on marketing and business, a member forum and monthly live Q&As and webinars.

With the launch of tTAP I’ve been offering consulting and coaching for creatives, and will soon be offering group coaching “mastermind” classes as well.

On January 1 I also launched a new website about creativity, 365 Days of Genius. It currently features articles from a variety of writers related to creativity, innovation and the way the mind works; daily resource links; a Genius Question of the Week; and 6-months of free creativity lessons. Eventually I’ll add a forum and other cool features as well.

Did you always know what you wanted to do (creatively) or has it been a process of trial and error to get to the point you’re at now? If it’s the latter, how did you decide what to focus on?

Oh for goodness sake, no! I was very artistic and creative as a kid — my parents thought I was going to grow up to be an artist — and I made art, played piano, violin, viola, and sang in a choir, but I was probably more focused on doing well in school than anything else. (That and animals — at age 3 I was going to grow up to be a cat.)

Everything changed when I discovered dance my last year in high school. I dove in like a woman possessed, and discovered my first true creative passion. Everything else took a back seat — way back!

I took a year “off” after graduating in order to focus on dancing, spent the following year in Letters & Science at UC Berkeley, then dropped out to go to Juilliard in New York, with great hopes of a successful career as a dancer and choreographer.

That is a story in itself, but the upshot was very painful, both physically and emotionally: I developed acute tendinitis and had to stop dancing altogether. I didn’t realize at the time that this was the end of my dance career, which was probably a good thing, as I might have done something drastic!

This period was a real low point in my life. I graduated from Berkeley and went on to get a Masters at University of Birmingham in England, but in the midst of it all I spent several years not just lost, but very disconnected from my creative self. Being young and naive, I truly believed that I’d had my one shot at passion, and could now only expect to trudge through the rest of my life.

Yoga artwork by Melissa Dinwiddie

Thankfully, I went on to discover a number of different passions over the intervening years, starting with calligraphy in my late 20s, then music — in particular singing jazz — and now writing as well. I like to joke that I discover a new passion about every decade, but I think that might be speeding up, as just this past summer I fell in love with the ukulele, right on the heels of (re-) discovering my passion for writing.

As for what to focus on, it’s taken me decades to realize and accept that I’m hard wired to be multi-passionate. This means that I’ll probably never be able to focus 100% on one thing. In some ways, this is a curse, because without that consistent 100% focus I’ll never achieve the level of mastery that I might. But on the other hand, it’s a blessing, because it just makes me happy to have so many things I love to do!

I think of my passions as pots on a stove. Only one or two can be up front at any given time, so the others stay simmering on the back burners until I’m compelled to pull them up front again. It seems that the pots often move around on a 3-4 month cycle. Some things stay on the back burner for years, but then my passion will flare up again and I’ll have a mad binge attack of creating in that particular expression before it recedes to the back burner again.

The good thing about being where I am now is that I understand my process a lot more than I used to. When I was younger I tried to do everything all the time, and felt terrible when of course that didn’t work. Thankfully now I’m fairly relaxed about not doing any particular thing at any given moment. I know that it will cycle around again when the time is right.

Have you organised your life in a certain way/made sacrifices in order to continue to be creative?

Well, I made the decision over a decade ago that I’d rather enjoy my day-to-day life than acquire a lot of wealth and “things,” though this never felt like a sacrifice per se. In the past year especially I’ve really worked set up my life to spend as much time as possible engaged in my creative passions. This is an ongoing process, and not always easy, but I’m committed to keep chasing after what I call my “evolving bliss.” (Or in my case, blisses!)

How do you define success?

To me, success is having control over how I spend my time, feeling content and happy with my life, and making a positive impact on the world. I’d be lying if I said money didn’t play a part – for example, when I first started making my full living from my art & creative efforts it was a huge boost to my self-confidence, and I definitely have financial goals that will feel great when I achieve them. But making money for the sake of making money has never been part of my definition of success.

What in your opinion are the positives and negatives of technology when it comes to both creating and promoting your work?

Technology has been a tremendous boon for me in so many ways! My wedding art & design business would not exist without technology. Although I create my artwork by hand in “natural media,” I print my fine art ketubah prints in-house (making great use of Photoshop and InDesign) and sell my work almost entirely online.

My latest “baby,” the Thriving Artists Project, wouldn’t exist at all without technology and the internet.

I also only really discovered my passion for writing when I started blogging. I’d tried to be a writer 15 years earlier, but didn’t stick with it. Now I like to say that I just needed to find the right genre — blogging – which didn’t exist back then!

That said, I spend a lot more time on the computer than I’d really like. So that’s a negative: technology is a huge time sink that sucks me in on a regular basis.

Card by Melissa Dinwiddie

Do you collaborate with others or prefer to work alone, and why?

So far I’ve mostly worked alone, except when making music, which is extremely collaborative. I love playing and improvising with other musicians!

More recently I partnered with Heather Claus on 365 Days of Genius, and that’s been a great experience, and very educational. Good communication is key, as is never taking anything personally!

I’m also going to be offering an online course later this year in partnership with another artist and online whiz, Kirsty Hall, and I’d definitely love to collaborate more, both in creative businesses and in purely creative non-business endeavors.

Is community important to you – either local or online – and if so, why?

Community is hugely important to me. I’m a very connection-driven person, and am happiest when I’m able to make a positive difference in other people’s lives. That’s one of the things that really appeals to me about the internet and social media — the ability to connect in ways that weren’t possible before.

It’s also why I included a member forum in the Thriving Artists Project. Since community has made a big difference in my life, I wanted to offer a way for my members to connect with each other and with me, so that we could support each other most effectively.

I’ve always found consistency difficult in terms of learning a craft and then practicing it regularly – is this something you’ve mastered and do you have any advice on how to maintain this?

I have certainly not mastered this! When I was a dancer, going to class every day (sometimes multiple times a day) was part of my life, and I was so driven to master my craft that it wasn’t a question. People often refer to my discipline, but I don’t feel like a particularly disciplined person. It’s only when I’m madly in love with what I’m doing that I’m “disciplined” about doing it! And since what compels me most cycles around among my various pursuits, the things I’m less compelled by at any given time get sorely neglected.

Perhaps if I weren’t so multi-passionate I’d be able to be more consistent. As it is, I’ve found that taking regular classes or lessons helps tremendously, since I don’t want to be behind the rest of the class, or make a fool of myself when I’m asked to perform and it’s clear I haven’t practiced!

I think the real key here is to find your unique motivators. If you know what drives you — whether it’s moving toward something you want, or avoiding some kind of pain — you can use that to help create systems to keep you en route to your goals.

Phew! I have no idea how Melissa fits all that in. Can you relate to her “multi-passionate” creativity? Why not say hello in the comments.

*This is an affiliate link to Melissa’s Thriving Artist Project, which in theory means I would earn a commission if you buy it, and you can currently get a free 30 day sneak peek inside so everybody wins! I’m a member myself and there’s some great content there already including interviews with Chris Guillebeau & Michael Nobbs, and a whole bunch of helpful creative people involved in the forums.

17 replies on “Artist & Entrepreneur Melissa Dinwiddie”

Great questions, Milo, and great answers from Melissa.

No, I don’t know how she packs it all in but I am impressed. Melissa is a really good teacher as well as artist and I have been thrilled with the resources available through the Thriving Artists Project.


Aw, thanks Kim! I LOVE to teach — as much as I love creating stuff — so it’s especially gratifying to hear when my teaching is working well. 🙂

You’re such a great addition to the TAP community — super glad to have you, Kim! Very impressed with how you’ve been integrating my suggestions in your blog, too. Keep up the good work!


Melissa, the honour is all mine 🙂

Kim, thanks for your comment, I totally agree. I can only begin to imagine the work that goes into pulling a resource like that together – I thought blogging regularly was hard enough!


*blush* I’m all smiley now.
And yeah, tTAP is a metric ton of work. If I didn’t totally love it there’s no WAY I’d be able to work this hard!
(And you’ll notice that my blogging is down to just once a week, with rare exceptions… )
Wish I could clone myself…


I’m worried about what you might achieve if you cloned yourself Melissa, maybe it’s best that science isn’t quite there yet 😉


Melissa you might just be the most awesomest person who has ever lived.

’nuff said.

No wait, it’s not enough said! lol. I have a lot of passions myself and I’ve struggled to get a handle on all of it. I guess maybe I *don’t* need to curtail it, I’ll just go with it.

I’m definitely going to keep up with your site and all your offerings. Thanks much!

Oh yeah, Milo, thanks for posting this. Peace!


Very inspiring, Melissa and Milo. Many times it appears as a problem, if you have many (creative) projects in mind and find it hard to focus. It’s good to see a positive way to deal with that situation.

Thanks for the interview.


Thanks Joachim! It can indeed be challenging, but when it’s the way you’re wired, there’s nothing for it but to figure out how to make it work for you. 🙂

Maybe if more of us modeled it, other multi-passionates would come out of the closet and join us. 😉


Um, excuse me (creak of closet door). I think I might be a multi-passionate…. I’ve think you’ve just clarified something for me. Could this be why I’m finding it so hard to be a clear-minded creative? I’m trying to juggle with fewer balls, but still keep dropping a few. It’s so hard to focus…


Very likely Elizabeth, it’s tough to prioritise when you have a lot of interests, and to some extent you have to accept that you need a fair bit of variety in your life I think!


Hey there,

I just came across your site, it’s great. I’ve had so many artistic avenues I’ve wanted to explore and I finally settled on creating my craft boutique (gotta plug y’all). Also, while showing my art to the world, I’m still charging on to figure out my enneagram type. It’s a whirlwind of searching right now! Keep creating and laughing! Thanks!


Hi Miss Billie, thanks for commenting, glad you like the site. Sounds like you’ve got a good balance of output and introspection there – the enneagram is a good tool for working out your ‘creative DNA’. Good luck with the boutique!


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