Why I quit freelancing

In December, I quit freelancing to start working as the Community Manager at The Theme Foundry.

I didn’t really know what to expect re: how the transition from freelance to full-time would go. In many ways, working for a small, distributed company is similar to my experience of freelancing, but I was also anxious about the potential for loss of freedom and flexibility.

One of my core desired feelings is boundless freedom.

Despite my fears, I couldn’t pass up the opportunity to try for this position, and I’m glad I didn’t. While I was quite happy with the sort of work I had been doing, and I was also happily booked several months in advance with work and projects, I had started to suspect that my career would stagnate, and I’m keenly interested in learning and growing.

When I first started with TTF, I only told a few people, and I was surprised and disappointed by the attitude and reaction of a couple of my freelancer & entrepreneur friends. To them, it was as though I had given up the good fight. I will always admire those who can carve out their own path and stalwartly stay true to their passions and goals, as many freelancers do. But I was actually quite intentional when I made this life change. Specifically, I was seeking the opportunity to:

Work with others: Even though I socialize on Twitter and Facebook while working, and scheduled weekly meetings with clients, I still experienced a great deal of isolation. When you’re a freelancer, you’re alone in your boat. The client/freelancer relationship is quite different from the coworker/coworker relationship.

That said, I’m also quite comfortable self-managing. Which is why a distributed team, with the sort of independence-valuing culture The Theme Foundry fosters is ideal. We’ve got boats. But our boats are tethered together.

So far, I’ve found the best part of having coworkers is that you get to listen to them chat with each other about things that you don’t understand at all. It’s been a tremendous opportunity to learn things that had previously only been on my periphery — and I expect will continue to fascinate.

Get a wider world-view: I worked my tail off to establish and then effectively market myself to my ideal client over the past year — and was successful at that, in my opinion. I found myself working for coaches, creatives, and healers.  And in truth, I found that all my clients were women.

That wasn’t really intentional, it grew that way organically because those are the types of people and businesses I tend to resonate strongly with. I speak those languages well, and it’s easier to communicate and collaborate.

However, I knew I would have to grow out of that niche if I wanted to expand my skillset. I wanted to work with a variety of people on a variety of projects, even those I wouldn’t necessarily choose for myself.

Bottom line: I wanted to get outside my comfort zone.

Increase bandwidth/Decrease scatterbrain syndrome: I’ve been blessed to work with some amazing people to create impactful changes through their projects. And I love that about the web in general.

But I had a hard time finding the bandwidth and capacity to get involved in the greater community projects I was keenly interested in while focusing on so many smaller client projects. That’s not to say that there aren’t awesome freelancers who can do just that, just that it didn’t work for me.

I’m a uni-tasker, not a multitasker. I know, do those kind of creatures even exist anymore? Being able to sit down with one set of overarching work goals has been so relieving, rather than switching rapidly back and forth between four or five different high level plans.

I will be the first to admit I’m still finding my bearings around this, adjusting and learning, but so far, I’m feeling confident that this was the right decision to make at the right point in my life.

And truly, I’m still a good fight girl, I’ve just transferred to a different front.

Sacred Saturdays and saving Sundays

Or, What I learned from scheduling a meeting on a Saturday and then subsequently missing one on Sunday

A few months ago I was chatting with a client about my email response times and working hours, which I specify in my welcome kit/agreement/contract-if-you-like are between 9 a.m. and 2 p.m. Monday through Friday. Now, before you get the impression I’m only working twenty-hours a week, those are just the hours that I don’t have children in my house. I am often in the position of catching up on writing or working after my kids are in bed, when they’re at their dad’s house, or otherwise preoccupied (I’m a big fan of the laptop on the back porch method of getting-crap-done). And that means sometimes, yes, I do reply to emails on weekends.

My client, who had recently moved from Spain, Siesta culture, was aghast. You should NOT be working weekends. Not even emails, she reprimanded.

Gosh, if only all our clients had such unreasonable demands, right? ;)

Last week was an unusually busy week for me, and I had a client who needed some follow-up support, and Saturday was just the best time for us to have an intense jam session on the phone. My kids were going to be at their father’s, and I wanted to catch up, so I set the meeting. We hopped on our meeting in the morning after breakfast. But by the time we finished, after lunch, I was drained (it was all very good work, don’t get me wrong, but still intense strategy stuff. On a Saturday).

After that, I just felt done in. My kids came home and I turned off my laptop and ignored email for the rest of the weekend. On Sunday morning, I suggested an impromptu trip to the beach to my kiddos, and on that impulse, we piled in the car and headed to Lake Ontario.

Feet in the sand. Check. Spirit restored. Check.

Not working on Sundays

Sunburn and awkward tan lines? Check.

Except I didn’t bother to check my calendar before we left, and we were so far north that I turned my phone off so I wouldn’t get charged for hitting a Canadian data tower. And I completely forgot that I had a business coaching session1 scheduled for Sunday2 afternoon. That I had paid for, mind you.

So by the time I re-entered the grid and saw her concerned, “Are you okay??” emails, I felt like a total dolt! Completely. Mortified.

One of the biggest lessons I’ve learned from being the Sassy Sibyl and struggling to make that business take off in a way that is sustainable, both financially and energetically, is that I am not my business. If I were the embodiment of my business, it would make sense for me to have meetings on weekends. It would make sense that the lines would blur between business/working/and life. But my purpose for being alive is not a function of the business I am in. If I believed that, none of it would be worthwhile.

This is an issue of boundaries for me. And I know other creative and heart-centered business owners struggle with it. In America, it’s drilled in our brains to work hard and get lucky. Well, how about work hard and have a heart attack at 55? Or maybe, work hard and miss out on your kids growing up?

None of those options sound appealing. And I don’t want to be out of integrity by forgetting meetings because my mind, body and spirit need to rest. So I’m declaring my weekends sacred and drawing that line in the sand.

With my toes. On a sunny beach.

How do you handle work and life boundaries?

The Deep End Test


I was a foolhardy child. Never bothered to foster a healthy fear of death till I was at least twenty-five or so. When I was six, overly excited about swimming with my scouting troop, I ran to the edge of the pool and jumped in the deep end. No matter the fact that I couldn’t swim. I sank to the bottom and was retrieved and resuscitated by a crew of friendly lifeguards and my troop leader. After which, I was promptly banished from swimming/running/otherwise not thinking things through.

That mortal awareness must has skipped a generation. My son thinks everything through in excruciating detail, and if things don’t add up, he’s not on board. For the most part, it’s a non-issue; he’s smart, funny, kind, and usually breezes through life. But when those fear buttons are pushed, he’s paralyzed by anxiety and negativity.

This morning he was spiraling downward, wrestling with all kinds of angst about going back to camp. See, on Friday, at his swim lessons, he worked up the bravery to try the diving board for the first time. But when he got to the end, he slipped and fell in. The instructors and the lifeguards were there to catch him. The nurse called me and said he was badly scraped and bruised. When I picked him up, he was covered in lacerations that ran from his wrist, all the way down his arm and back. He was not happy.

And he wasn’t happy this morning when I told him to go back and try again. It’s hard. I don’t like it. What if I hit my head? What if I never pass the Deep End Test?! 

All of his protests I heard and acknowledged.

Sometimes I’m parenting and I see myself from the outside. This was one of those occasions. A little voice was whispering in my ear, “This is a LIFE LESSON opportunity.” While my Mel-brain was grappling with not wanting to be a hard-ass parent who pushes their kids to do crap they truly hate.

Let me let you in on my little parenting secret. I’m a dedicated follower of the parenting school of wing-dinging it. In fact, we’re all just making this up. And we’re doing it on the fly.

I took a deep breath, and then I explained (more or less this), “Sullivan, you’re going to go to camp. You’re going to continue taking swimming lessons. And you’re going to give it your best effort. Some things are hard. Some things you have to do even though you don’t like it. Sometimes we try and we fail, but we should never be afraid of failing. You’re safe. You’re brave. And you’re strong. I know you can do this.”

What I didn’t tell him is that I never learned to swim after I was pulled from the swimming pool. And it doesn’t bother me, except when I see the sailboats on Cayuga Lake. When my stomach twists up with a longing, but then I think, what if I fell in? Or worse, what if one of my kids fell in?

His lip was quivering and it was about time to leave, so I scrambled. “Okay. When you pass the Deep End Test, I will take you to the mall and buy you any video game you want. ANY. VIDEO. GAME.” And I could see the gears churning away in his head; calculating all new cost/benefit ratios based on the addition of this shiny new carrot I was dangling. He brightened. And agreed.

It’s profound how my children’s struggles are a microcosm of my own. There’s always a Deep End Test lurking around the corner, isn’t there? And if we back away in fear, we’ll be stuck treading water forever.

Maybe we’ve fallen. Maybe we’ve been battered and bruised. And maybe it’s scary as hell. But if we face up to it, there’ll be a new Mario Kart game at the end of that long, dark tunnel… or even sailing lessons, perhaps.