Getting Comfortable with Reinvention in Life and Business

The most common question I’m asked is, “Tell me again, what is it you do, exactly?” My mom still doesn’t really know. And you might be wondering the same thing. I’m a designer, writer, business owner, mom, brand strategist, and digital media consultant. I wear all these hats under a brand called Wit & Delight.

Getting Comfortable with Reinvention in Life and Business – Wit & Delight

The job of a designer is different than it was 10 years ago. Above is a smattering of work I’ve produced over the past couple years. The lines have been blurred between graphic design, content creator, video editor, copy writer, product designer and art director. These days agencies are in hot pursuit for the elusive “swiss army knife” creative.

Reinvention isn’t new for designers. We all have to face the process of reinvention throughout our careers, and while it’s full of unknowns and what ifs, we’re really, really good at problem-solving. We’re blessed with a design education that uniquely equips us to turn what-ifs into things you can touch, feel and experience.

But what often happens when you spend your career solving hundreds of “what if” problems a year? We forget to turn the lens on ourselves.

Like many of you, my career path is punctuated with a series of roadblocks, or as I like to call them, pivots.

When something doesn’t go your way, or a roadblock presents itself, we have to decide how to keep moving forward. This is where you pivot. In my experience, reinvention— the process of pivoting and taking on a new strategy/career/industry/etc., rarely happens when we’re sitting comfortably.

Here’s my story told in a series of pivots.

Getting Comfortable with Reinvention in Life and Business – Wit & Delight

Pivot One: Embrace Fear, No Parachutes Included

W&D was born out of fear of losing my job. It was 2008 and the economy had tanked. I worried my job at a small design firm would get cut. It was the push I needed to get my portfolio and blog started. Instead of worrying about the lack of jobs, I thought about ways I could seek out clients through building an online presence. A design education gives you the ability to turn fear into opportunity by seeing solutions where there were roadblocks.

Getting Comfortable with Reinvention in Life and Business – Wit & Delight

Pivot Two: Bet On Your Own Grit, The 24/7 Job

Once I started Wit & Delight, I spent almost all of my waking hours outside work putting the website together. I had no idea how to code, but I had a very specific vision for how the site would look and operate.

In order to stand out in a sea of design and lifestyle blogs, I decided to present our content in the form of a grid, so readers could easily scan for the pieces they were most interested in.

This was before Pinterest or easy-to-use programs like Squarespace had come along, so I had to find some raw code close to what I wanted and hack it together myself.

I had no coding experience and had literally no idea what I was doing.

I crashed the site almost every week, with most of my design decisions being based on what very little control I had over spacing, kerning, borders, etc. I put hundreds of hours into it, for a few months before I got it in a place that was presentable. It was far, far, FAR from perfect.

Getting Comfortable with Reinvention in Life and Business – Wit & Delight

Pivot Three: Ignore Everyone, Even Your Own Critics

There was a pivotal moment when I shared my website with my co-workers. Almost every person I talked to told me it was a bad idea to entertain leaving the design community and then promptly critiqued the “very confusing and unintuitive” layout of my site. Thankfully I had two wonderful bosses who believed in me and have supported my endeavors, regardless if they “got it” or not.

Don’t underestimate your ability to see things that no one else can, it allows you to come up with a solution with what’s in front of you.

Taking a different path means meeting some resistance. What I’ve learned is criticism that doesn’t offer constructive feedback is often more about the critic’s fears and insecurities and less about what you’re doing. It’s helpful to look for the difference, and even more important to find people who will give you honest feedback.

Getting Comfortable with Reinvention in Life and Business – Wit & Delight

Pivot Four: Let Go

Sometimes reinvention means letting go of a path or plan.

When Wit & Delight took off, I was exhausted and disheartened by social media in general. I didn’t feel excited about what we were making and felt disconnected to the content. I took this opportunity to think about what I had to offer our readers. I had just spent 12 months working on my inner battles with perfectionism and balance, and I thought it was a great time to show more of the process, more of the person, and more of the thought that went into each image I put out into the world.

The results blew my mind. Not only was our readership up 200%, we were actually helping people work through problems and had an entirely new content model on our hands.

Now, I’m turning towards the next phase of Wit & Delight– our own product and e-commerce shop. It’s been hard. Countless hours of designing, getting back to my branding roots, and of course– second guessing myself the entire time. I believe we’re still in the process of pivoting, but here’s just a little taste of what’s to come in the next couple months:

Getting Comfortable with Reinvention in Life and Business – Wit & Delight

Getting Comfortable with Reinvention in Life and Business – Wit & Delight

Getting Comfortable with Reinvention in Life and Business – Wit & Delight

Getting Comfortable with Reinvention in Life and Business – Wit & DelightGetting Comfortable with Reinvention in Life and Business – Wit & Delight

——

Everyone reading this post will reinvent themselves multiple times over a career.

Mine was Wit & Delight.

It was born out of fear, made from grit, strengthened by critics, and sustained with a bit of magic.

Every phase of reinvention got me here: 3.1 million followers, billing ~100 projects a year, 4 team members, 8 paid contributors, 5 product lines in development, and a new 6,000 square foot studio.

And it all started with one little pivot.

  • Kate–your raw and honest posts are the reasons that keep coming back to your site. It’s awe-inspiring to see where your journey with Wit & Delight has taken you. And posts like these always come at a time when I need that extra push, so thank you.

    I would say your job title should be “being awesome”! 🙂

  • Love reading about your story, Kate. Reminds me of an episode of Hidden Brain I’ve been thinking about a lot lately. The ep is called Getting Unstuck and it’s about using design thinking as a means of figuring out where to go next. Instead of overthinking and trying to create the ideal life for yourself in one fell swoop, it’s better to try a series of experiments, learn from them, and keep doing that indefinitely. Fail early and often. Seems like that’s the mentality you’ve had all along.

    Also I cannot WAIT for those products to come out. They’re beautiful.

  • as a dedicated reader of W&D over the last 5 years, it has been absolutely incredible to see W&D grow into what it is today. You draw sooo many readers because our society is hungry for real, raw, genuine, relatable content- and you deliver just that. Thank you for being so candid and vulnerable with your business-and congratulations on the W&D success thus far!

  • This was so great to read. As a new blogger finally taking this thing seriously, it’s so easy to forget that even the blogs we admire started from scratch, and that everyone was once sheepishly hesitant to share our ideas with the people we know. Thanks for sharing and for being the inspiration that you are!

  • Hi Kate!

    I would love to learn how you gained readership up to 200%? My blog is a working progress, and would love to know how you market yourself. Love reading about your start to Wit and Delight.

  • Hi Kate!

    My internet crashed, so this is Take II of my comment – I apologize if two end up popping up.

    Yet another amazing article! This is why I have been a loyal reader of yours for close to 7 years now! I am so excited for this next W&D phase. Especially the e-commerce page. It sounds a bit like the style Violet Grey has, only this won’t be just beauty products – I am quite a fan of this new design!

    Best of luck.
    Cheers,
    Your VA friend, Jamie

  • Kate, I’ve enjoyed following your progress and it’s so great to see you succeed!! I love the sneak peek at your product line, can’t wait to purchase.

    Best of luck!

    xx Kate

  • “What I’ve learned is criticism that doesn’t offer constructive feedback is often more about the critic’s fears and insecurities and less about what you’re doing.” YES. Huge ah-ha for me. Thanks so much for all your honesty, Kate!

  • Thank you, I needed that. “W&D was born out of fear…” I’m there and working to silence the internal critics.

    Anne Lamott (1994), speaks to moving forward in the face of fear (Bird by Bird: Some Instructions on Writing and Life). She advises the reticent to, “close your eyes and get quiet for a minute, until the chatter starts up. Then isolate one of the voices and imagine the person speaking as a mouse. Pick it up by the tail and drop it into a mason jar. Then isolate another voice …Drop in any high maintenance parental units, ..contractors, lawyers, colleagues …anyone who is whining in your head. Then put the lid on…watch all these mouse people …trying to make you feel like shit…” Find the volume switch and turn it down. “Leave it down and get back to your shitty first draft” (1994, p. 27).

    Your approach is less violent :0)

  • I’ve been a reader since (almost) the beginning and have loved watching your space shift and evolve. It has always felt like coming home. I’m glad you pivoted.

  • Great read for taking any kind of jump or initiative in life! Could you also do a post about creating your own blog/website/business? I know this seems really vague and maybe you already have it, but are there certain skills or products that helped/help you do everything you do with the website?

    Thank you for all of the great content!

  • Thanks so much for sharing your journey! My mother says much the same thing to me, despite her having not even read a single post from my blog. You’re absolutely right that you have to block out everyone, including the critics. Reinvention only works if it’s you doing you.

    I love the new line – can’t wait to see it!

    http://www.shessobright.com

  • This is my very first visit to your site and I this post really rings true to me as a fellow woman entrepreneur trying to forge her own path. Can’t wait to read more!

  • Love this post for so many reasons!
    1. It’s authentically YOU. Your voice, your story and as only you can tell through your eyes.
    2. It’s so REAL. I struggle through my own pivots to see them as a pivot towards a longer journey, a bigger story – and not the end state. Social media + the internet make it way too tempting to check progress alongside everyone else, but this post is a great reminder that each pivot is yours and yours alone and W+D wouldn’t be where it is without them.

    Always so good with your words…and can’t wait to see the next pivot LIVE. The product sneak peeks look amazing (of course) and I can’t wait to stock up…

    xoxo.