Time for a Change - WilloLovesYou.com

Time for a Change

Seven years, two businesses…
For the last six months I’ve been looking back at all that I have learned running my own business(es) over the last 7 years.

I started my first business almost by accident, after being laid off from my last “real” job in 2003, where I worked for 3 years as the Lead Web/Flash/Graphic Designer, at a small firm in Potrero Hill. Wasting no time in the few weeks after I got the news, I quickly put together a quick website and business cards to launch WilloToons Baby, offering custom wall painting for nurseries and playrooms. However, it wasn’t long before I started getting inquiries to do freelance Web & Graphic Design, and next thing I knew I had a full client load.

The years to follow were full of a lot of great experience. I’ve had the pleasure of working with some great clients; designing & launching sites for both small and large organizations. I learned valuable skills around managing projects, timelines and client expectations. I hired developers, copywriters and did all my own bookkeeping. And I learned a lot around managing my time, and maintaining a healthy work/life balance. (Raise your hand if you relate to that one. A common side effect of being a passionate, driven person, I suppose, but I feel like I could write a whole book on it! 🙂

However, after a few years, I started thinking, what’s next? I really didn’t want to start my own design firm, but instead – for as long as I could remember – I’d been wanting to do something more with my illustrations. So, in May, 2007 I dove in to do just that: designing, producing and launching WilloToons – my super fun product line of tees, onesies & bibs (that since then has developed into greeting cards, jewelry, totes & more) – where geek meets rock ‘n roll! [Note: If you’re interested in reading about this transition, check out my launch post or my mission/vision post.]

Up until then, most of my professional experience had been in services, but I was ready to learn… and boy, did I! The last three years I have learned a LOT about product development, e-commerce, marketing, Quickbooks & bookkeeping, inventory management, COGS, cashflow, customer service, you name it! And honestly, while I could have done a lot of things differently (read: better/smarter/faster) in hindsight, I feel like I’ve been fairly successful, given my means and experience prior to diving in. I feel grateful that in this time I have met friends, and gained happy customers and fans, all around the globe. It’s provided me the opportunity to step into more speaking roles, sharing what I have learned, and consulting other crafters and small business owners in everything from how to get their business online, to marketing through social media, crafting your community, and to some of the more philosophical and psychological realms of being a small business owner (yes, this is another area I could write a whole book on :).

It’s not you, it’s me…
WilloToons has been my baby over the last 3 years, and I’m really proud of all that it’s become, but I’m at this place now–7+ years in, owning and running two fairly successful businesses–where I have some options. I’ve actually been wrestling with this decision for almost a year, really. Because, while I still haven’t seen WilloToons to the full potential I see in my vision, I’ve also learned what it would take to realize that vision. Therefore, causing me to seriously reevaluate if this is even the business that I want to continue growing. I mean, I of course still love illustration and design, I’ve just started feeling like there’s more I can do with ALL of my skills.

It’s kind of like that point in a relationship where you’re like, “sure, we could try to work on this… but I think we both know we need a break.” It’s been rather difficult to get clear on that. Like any relationship, I want to work on it. I don’t want to give up on it, but instead I want to do everything I can to know that I’ve taken responsibility for my part in all of it, and get clear on what it would take to make it better, or to know (really KNOW) that it’s best to just let it go.

Now, I’m not saying I’m letting go of WilloToons at all, which I think has been a big scary thought in this process for me. WilloToons is a part of me! I am WilloToons! :p But, thankfully the store runs itself for the most part right now (with big thanks to my Merchandise Manager, Jen!), and I have a relatively steady stream of client work that comes my way, so I’ve sort of had the luxury of doing this soul searching. I knew one thing was for sure though, just like in any relationship, figuring out what was best for me, meant taking care of myself first. And that, for me, is all about getting back to my creativity. My source. I want to get back to designing, creating, and giving birth to new ideas. I’ve needed to for a long time now, but as any creative in business knows, it can be hard to do that while you’re busy keeping all the plates spinning!

So, over the last few months I’ve been REALLY digging in to look deeper at what I want. For one, after juggling SO MUCH over the last 7 years, I’ve really felt called to unplug a bit more. Since I’d been feeling lost and stuck, instead of allowing myself to stay there, I decided I wanted to flip my life on it’s head, shake it up a bit and see what wanted to rattle out. A big part of this has been clearing and making way for the new to come through. First and foremost, decluttering and refreshing my wonderful little home, that I’ve lived in for these last 7 years, and worked out of for the first 5. Which even included getting rid of my TV, and all the habits that surrounded having that in my space, in order to transform my living room into more of an art studio… huzzah!

So much happened exactly 7 years ago, that has led me into my life as I know it right now… that I think mostly I’ve had to really allow myself to release who I have been – my identity – and how I have let this time, and these businesses, define who I am. I have *reveled* in owning my own business, and launching my dream! I mean, so awesome, right? Aren’t I living the dream, of what so many people in Corporate America™ wish they were doing? So how could this be not enough for me anymore? These are all rhetorical, mind you, but you can imagine what a rollercoaster it’s been trying to make heads or tales of it. All I knew was I just kept hearing my mind say, “I want to be a part of something bigger.”

Well, thankfully these last few weeks have *finally* brought some clarity… YES!! And the answer? Waaaaait for it…

I want to be a part of something BIGGER!
That’s what it comes down to. I have accumulated SO many awesome skills over the last 7 years and I have SO much to offer now more than ever! I have done this. I have worked on my own and experienced developing and running a business two businesses, giving me experience in both services and products; I’ve managed my time, clients, and employees; I am passionate & motivated, and not afraid (in fact, downright good at) working hard to make something happen, and I want to be a part of a team!

So, over the weekend, I started getting even clearer on what this means for me. Here are some of the questions I have been asking myself:

What does it mean (to me) to “be a part of something bigger?”

  • I see so many of my friends, whom I respect so much, accepting positions or starting companies that are developing products on the cutting edge. The tech space has changed SO much over the last few years, and in my opinion is truly more exciting than ever!
  • I want to work and learn from other business owners, and professionals who compliment my skills.
  • I want to have the means to hire and manage a rockstar team.
  • I want my creativity and all that I have to offer to reach a larger population.
  • My WilloToons’ mission is to celebrate individuality and expression, so how can I do that on a larger scale?

What are the qualities that are important to me, in feeling good about working with another team or company?

  • Forward thinking
  • Social/economical awareness
  • Environmental awareness
  • Fun, easy going people, with healthy communication
  • An understanding around what it takes to build a smart team. i.e. Building a team where members are encouraged to work within their strengths

What skills come naturally to me?

  • If I look at the last few years in this business, I think one of the most rewarding aspects has been helping people. Through my speaking engagements, teaching, consulting and connecting people… it’s what comes so naturally to me! I love offering perspective to other creatives and small business owners, sharing my process, mentoring and giving tips on how they can make money, develop their community, step into their creativity. I’ve loved helping my clients; I enjoy the communication, knowing that I’m making their lives/businesses easier (not to mention prettier!), and helping them position themselves for success.
  • Design & illustration (of course), but now even on a broader scale, with creative direction & strategy. I’m a natural problem solver, big idea thinker, and rapid implementer. In addition to the joy I’ve experienced designing my own site/shop & product line, I’ve taken great pride in working with my clients, designing and developing their vision, and consulting them through the various phases of growing their business.

What am I most passionate about in business? aka What do I have to offer?

  • Excellence in Design & Usability
  • Awareness and Experience in Social Commerce
  • Big Vision & Creative Direction
  • Developing Strategy for Implementation
  • Marketing, Community, Communication, Connection, Promotion
  • Management: Client, Team & Product

Now, how can I wrap all of that up into my next step?
Honestly, I’m not quite sure where all of this is going to take me, but, being the excitable, positive person that I am, you can bet I’m on the edge of my seat! 🙂

I envision myself being a part of a core team. So, whether that means I’ll be starting up another company of my own, or joining a company at the ground floor (or close to it), I’m really looking forward to being able to really have an impact, utilizing my strengths and passion for the ultimate good of a great product or service. I’ve been talking to some friends, and we brainstormed a few things. Even that it might be a good idea to talk to some of our friends who are investors, or on Boards of startups who have the business, finance and tech aspects figured out, but need more creative direction. Who knows, but I’m putting it out there, and I’m ready!

Thanks so much for those taking the time to read this, and so many of you who have been with me on every step of these adventures thus far. I feel incredibly grateful for every single one of my friends and supporters out there, so seriously, thank you. I’d love to hear if you feel I’m missing anything in all of the above, or if while reading it you had a vision for what you see me doing with all that I have to offer. I’m looking forward to taking this next step, and you know I’ll be sharing it with you… that’s what I do! 🙂

About the Author

Willo Sana has been empowering entrepreneurs who are standing on the precipice of their next level for over 20 years. An international keynote speaker and sought-after Transformational Business Coach, Willo's experienced and intuitive guidance has served as a catalytic force for visionary business owners around the world. Anticipation is building for Willo's upcoming book, Double Down on Your Genius: Own Your Gifts, Align Your Actions, and Flourish in Your Calling, set to release in 2023.

Leave a Reply 47 comments

gene x - June 30, 2010 Reply

Great post – I know how it can be as a fellow business owner. I’m sure whatever you decide that you’re gonna keep making an impact and I look forward to seeing how that journey manifests itself… and to toast you along the way!

    Willo O'Brien - June 30, 2010 Reply

    Right on. I know you can relate, Gene, and I love talking small business with you. Thanks for all of your support!

Matt Hendrick - June 30, 2010 Reply

Congratulations Willo – you’ve really captured your thought process well, and I can totally relate! A few years back I went through a similar transition in my life, when I made the decision to boldly step forward into the unknown, simply because I knew inside that it was the path I was supposed to take. It’s clear you’ve learned a TON about ALL aspects of business over the past few years, and your passion for being a part of something bigger definitely comes across – not only on this page, but in the short conversation we had last weekend as well.

I wish you the best of luck. If we had the $$ to pay you I’d ask you to be a part of our team in a heartbeat!

    Willo O'Brien - June 30, 2010 Reply

    Thanks, Matt! It is a big step – at least it feels like in my world anyway – so it’s rad you get that. Awesome meeting you the other day, and talking about how exciting this time is… I look forward to watching where both our paths go! Rock on.

Emily Goligoski - June 30, 2010 Reply

I’m proud of you gal.

    Willo O'Brien - June 30, 2010 Reply

    Thanks, m’lady! You’ve been such a wonderful supportive friend. <3

Janette - June 30, 2010 Reply

Lovely. And exciting. 🙂

    Willo O'Brien - June 30, 2010 Reply

    Yes, yes! Thanks for reading. 🙂

Humuhumu - June 30, 2010 Reply

Here’s to bold moves! I look forward to seeing what you have cooking this time next year.

    Willo O'Brien - June 30, 2010 Reply

    YES! 😀 Thanks, Humu! xo

Steven Holmes - June 30, 2010 Reply

Hey Willo,

Loved this post. It was clearly well thought out and I also felt like there was a stream of consciousness element to it. To use a card playing analogy, you know the hand you’ve got but you’re not quite sure how to play it. That’s the rub, eh?! There are truly many options.

First, if I captured it correctly, you’ve identified a list of skills that are divided between hard and soft skills. Understanding web design, User-Interface usability, marketing (traditional and new media, including social) and other hard skills are relatively easy to translate into nearly any industry or organization. IDEO could use a good user-interface expert, or maybe a content provider, like an ad agency, or maybe Gap/Banana/Old Navy, might need somebody with strong community building skills on the now classic social platforms like Twitter, Facebook, etc.

But it sounds like the soft skills are the ones that have you really fired up and tuned in to this expanding work-life purpose that’s bubbling up in you, e.g., Big Vision + Creative Direction, Strategic Planning and helping / motivating people with goal setting and growth. That is a bit more challenging to narrow into a specific type of role. I mean, the driver of vision is typically the C.E.O, right? C.O.O’s implement the vision…C.M.O’s create excitement around whatever the promise is of said vision, etc. You’ve done all that as a business owner, but on a larger scale it often is more difficult to find those roles.

I think your needs regarding the type of team or organization you join (or create) could be the most useful in channeling this move into a specific direction. A good friend of mine in Marin has realized that for her, the environment she works in has more importance than what she’s actually doing. It seems like for you, it maybe carries equal weight? Working with, or for, a forward-thinking organization with a bent towards sustainability, etc.

I don’t know. You’ve got much to offer for sure and with all your creative energy, I’m sure you’ll find the right place to share your skills and passion.

The bottom line is every organization needs a passionate difference maker with a positive attitude. You’ll find your way.

    Willo O'Brien - June 30, 2010 Reply

    Hehee… maybe that’s my new title? Passionate Difference Maker. :p

    There truly are SO many options, but I think the overarching theme is that, after these last 7 years, I feel really confident I can dive in and tackle most any challenge set before me and make the best of it. Hmm, yup, you had it right the first time: Passionate Difference Maker. haha.

    Thanks for the thoughtful comment, Steve… and for all of your support here & on FB!

stephdub - June 30, 2010 Reply

here’s to allowing, manifesting, creating, welcoming, embracing, encouraging, and designing brilliant new levels of success and contribution.
i love you pretty, and i’m so grateful to be standing along side you through this energizing and exciting next step.

    Willo O'Brien - June 30, 2010 Reply

    I love YOU, pretty! I absolutely loved that you showed up this afternoon, right as I was hitting publish on this. It was like the Universe knew I needed to have some bright little ray of sunshine there to give me a kiss on the cheek, hold my hand & say “Go for it, woman, I got your back.” You’re the best. <3

Kevin Smokler - July 1, 2010 Reply

Points of decision are where we test our mettle, and see if we can act with thoughtfulness instead of fear. Well done for bringing your best self to the table, kiddo.

    Willo O'Brien - July 1, 2010 Reply

    That is such a great way to put it, and reaffirming. Thank you, Kevin!

Clintus - July 1, 2010 Reply

Good luck girl!

    Willo O'Brien - July 1, 2010 Reply

    Thanks, yo!

Andrei - July 1, 2010 Reply

Good luck with your endeavors, Willo! Discovering yourself and what you want is one of the most difficult things sometimes..

    Willo O'Brien - July 1, 2010 Reply

    Truth. It definitely hasn’t been easy, so it feels great to feel like I can finally see the light! 🙂 Thanks, Andrei!

April - July 1, 2010 Reply

High five, Willo! It’s so much easier to keep going than to question what you’re doing with your life. I’m so glad that you’re putting yourself out there to see what comes from this. All the best of luck to you! I know that you will see your desires met.


    Willo O'Brien - July 1, 2010 Reply

    Hi five, to a fellow creative who listens to her heart & follows her passion. Thanks, April! xoxo

Ethan Bloch - July 1, 2010 Reply

Let me know how I can help… excited for what you do next!

    Willo O'Brien - July 1, 2010 Reply

    Will do, Ethan, thank you so much.

laura - July 1, 2010 Reply

Can’t wait to see where you end up Willo – you have so much to offer, and indeed, amazing things are happening in technology right now.

    Willo O'Brien - July 1, 2010 Reply

    I can’t wait either, for both of us… and then we’ll celebrate! 🙂

Jay Goldman - July 1, 2010 Reply

Willo —

Like everything you do, this was awesome. I love that I’ve been a tiny part of Willotoons for the last few years — I can’t wait to see where this new direction takes you! The other parts of the something bigger will be super lucky to have you.

Let me know how I can help!

— j.

    Willo O'Brien - July 1, 2010 Reply

    I’ve been lucky to have a rockstar NBFF like you in my life. All of your feedback, perspective & support has been awesome. Stoked to see you out here soon!! xo

Aletha - July 1, 2010 Reply

I love that you have reached this clarity, and know you are exactly where you need to be at the perfect time…can’t wait to see what happens! Sounds like you are ready for your tarot reading soon 🙂 xo, aletha

    Willo O'Brien - July 1, 2010 Reply

    Thanks, love! Yes, you get it… getting to clarity can sometimes be like wadding through a thick mud (while carrying a boat on your back!), so this feels REALLY good. I’ve reached the shore & am ready for the next step. A reading sounds divine! Think we can fit it in before I leave on July 14th?

Mamacita - July 1, 2010 Reply

Successful, Proven, Driven, Ball of Fire……..someone is going to get an incredible asset to their business! Be particular….you deserve it and have blossomed to greater things!

    Willo O'Brien - July 1, 2010 Reply

    🙂 aww, thanks Momma!! <3

Karrie - July 1, 2010 Reply

I love this post. And I love that you put so much thought and heart into it. It has been a joy watching you rock the last 7 years. I am just excited to see you go, go, go!

    Willo O'Brien - July 1, 2010 Reply


Ben Lewis - July 1, 2010 Reply

I was fortunate to have an “office” right next to Willo when I launched my business, Engage As You Age. She’s inspiring, a hell of a designer and I’d recommend her to any company. I’m sad to hear that WilloToons won’t be the focus anymore but excited to see where she next lands. If anyone wants to hear about how great it is to work with and around Willo please get in touch. I think the world of her and wish I could afford to bring her on fulltime and pay her the 500K a year that she deserves 🙂

Good luck Willo!

    Willo O'Brien - July 1, 2010 Reply

    Hahaa, you’re awesome, Ben. Thank you. And I’m proud of you for not including some self-deprecating comment about how I excel in having to listen to cold calls from the loud guy in the next cube over. :p

Ben Lewis - July 1, 2010 Reply

The cold call days are over. Folks are calling me now! Can’t wait to see how many more calls come in once the new website is up and running 🙂

Peter - July 1, 2010 Reply

Stands and applauds. Love ya.

    Willo O'Brien - July 2, 2010 Reply

    Thanks, babe.

Sarah Lane - July 1, 2010 Reply

Go Willo!! Can’t wait to see where the next doors lead… xo

    Willo O'Brien - July 3, 2010 Reply

    Thanks, Sarah! <3

Deema Tamimi - July 2, 2010 Reply

This is such a great post! Thanks so much for sharing it. Congrats on the self-discovery and being able to document your thoughts so well. You will do amazingly well whatever path you choose and anyone who gets to work with you will be very lucky :). Good luck on your next adventure. I look forward to hearing more about it!

    Willo O'Brien - July 3, 2010 Reply

    Thanks, Deema! As you heard in my voice the other day, I’m very excited about where this next step will take me. Gotta love a blank canvas like that, huh? 🙂

Nathaniel - July 3, 2010 Reply

Yo Willo,
I started skimming this, but quickly realized I needed to stop and actually read! I just have to say, this is some fantastic thinking; it’s instructional isn’t it… this is how we can truly maintain our happiness and health.

What I think is also very clear and wonderful is that we all want the best for you and recognize how the best for you is the best for us (society). This phenomena should be no different for you than it is for me and my circles or others and theirs. We all need to be doing this sort of thinking… staying dynamic.

    Willo O'Brien - July 3, 2010 Reply

    Yes, yes, Nat… you get it. How can we serve the world with our skills and passion? It’s a great question, and inevitably delivers the best for all involved. Thanks for reading.

David Prager - July 5, 2010 Reply

You’re truly an entrepreneur and innovative thinker – can’t wait to see what comes next! Would love to help in any way I can!


    Willo O'Brien - July 7, 2010 Reply

    That means so much coming from you, Prager, thank you!! xoxo

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