The Eight-Year Escape Plan: Interview with Tsilli Pines

It’s a new month, and time for a new profile. My friend Tsilli Pines recently quit her job to go full-time with the side business she’s been building for the past three years.

Yay! Congratulations to her.

And when we were talking, she told me how she had worked at the job for eight years, and has spent the past three years carefully building her business to the point where she could take a big leap.

Entrepreneurs are often thought of as embracing risk—but I think this is a bit overrated. In Tsilli’s words: “I’m very conservative about making decisions. I probably could have quit the job last year, but I wanted to wait until I was absolutely sure.”

I thought this was fascinating, so I asked her to tell me more. You can read her answers in our interview below.

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One month ago you left your job of eight years to strike out on your own. How does it feel? 

It feels like freedom!

However, I had a great job working with great people, so leaving was bittersweet. I learned much of what I know and became the designer that I am working with Fine Design Group, and they gave me a lot of room to grow in the years I worked at the studio.

Then I hit my stride as a designer and started thinking about what I’m meant to do in the long term. I found myself yearning for total authorship. So while the client work I was doing in the studio was challenging and fun, I wondered what I could do if I were my own client.

Tell us a little about your business. What’s a ketubah? Who are your customers, and how do they find out about you?

A ketubah is a Jewish marriage contract. It was traditionally used as a legal document and is now regarded more broadly as a statement of commitment, ritual object, and work of art.

There is a long history of the ketubah being interpreted as an illuminated manuscript, but there aren’t many takes on the form from the perspective of modern design. My clients are design-minded folks who have a hard time finding something that fits with their style but want to include this tradition in their wedding. Most of the pieces I make are for Jewish or interfaith couples (where one person is Jewish and the other is from another tradition), but I’ve also made Quaker wedding certificates, which are similar documents.

Many people find me online—this is a product people search for pretty specifically. Now that I have been doing this for several years, I’m also getting referral business from happy clients. I try to take really good care of people, so it’s the highest compliment when someone recommends me.

How did you build the business on the side while working full-time?

I built the business really slowly and organically and fit it between the cracks. Two years before I launched my website, I met the owner of a Judaica shop in California, who encouraged me to try out my designs through her store. I worked up two prototypes and the day after I dropped them off, I had my first order.

For those first two years, I only had a handful of clients, because it was all I could handle while getting my head around the process. I learned the ropes by putting one foot in front of the next, getting guidance from the Judaica shop and a few rabbis, and making lots of mistakes.

After that initial period of incubation I felt confident that I had the basics under control: how to work with different texts and what the rules were around them, how to make the pieces, how to package and ship them. But I had never worked directly with any clients because I had the shop handling the first steps of the process. It was a wholesale relationship and I wanted to create a direct relationship with my clients.

I requested a chunk of time off from my job—a combination of vacation I had built up and unpaid time—so that I could focus on taking things to the next level. I got a month off and in that time, I developed a few more designs, designed and coded a website, figured out how I would take direct payment, researched ways to improve my process, and started doing PR to get the word out.

Knowing that people were increasingly looking for their ketubah online, and being a web designer by trade, I focused on how to make myself most visible online. I decided early on that besides having an easy-to-use website that was optimized for search engines, blogs would be the best way to raise awareness about my work. I already followed a lot of design and wedding blogs because I was interested in their content, so I wrote a very simple email introducing myself politely, with a few images of my work. The response was wonderful and I immediately became visible.

Tip from Tsilli: For folks who are looking to market their work online, I highly recommend Grace Bonney’s generous notes about how to approach the press and most especially this round-up from design bloggers about they like to be approached. In fact, the entire Biz Ladies series is a huge help.

Having an online business makes it easier to do on the side. I determined a reasonable process for fulfilling orders, and then I built a minimum turnaround time around that. Having limited time forced me to think about how to do the work most efficiently. I batched my email responses and did the work that could be done in bursts in the evenings and early mornings. The more involved work of actually producing the pieces was done on the weekends when I had entire days to get into the flow.

But I won’t lie: the beginning was insane. I was basically working two jobs, and my husband was helping me build the infrastructure—also on the side, since he has his own day job. He continues to support the project to this day. I couldn’t have done it without him.

It got to the point last year where there weren’t enough hours in the day, and I could only be reactive in fulfilling orders, rather than proactive in my business planning. It was clear that something had to give. But after four years of growing slowly, I finally felt confident that I had a viable business, and that allowed me to leave my day job.

When did you first think about quitting the day job—was it something you planned from the beginning of the startup, or was it after things began to grow? 

I am a very cautious person and entrepreneurship always seemed risky to me. For many years, I focused on finding the best possible job working for other people in order to avoid that perceived risk. I found the perfect job, but after putting in a good chunk of years, I started to wonder what was next for me.

I always knew I wanted to create something of my own and was drawn to the dream of being a working artist rather than a commercial designer. But I didn’t really see how the money side would work.

As I’ve grown my own practice, I’ve become increasingly entrepreneurial about it, and the small successes have encouraged me to push ahead. I now see the larger picture and realize that there are so many directions I can take things. This was harder to see when I started out. The path has appeared beneath my feet.

Did anything go wrong in the early development of the business? (If so, what did you learn?)

Oh, so many things have gone wrong. Luckily, they have all been fixable. Packages have gone missing, equipment has failed, mistakes have slipped past both me and my clients, all kinds of things! But with determination and a positive attitude, nothing has been insurmountable.

A lot of the learning process about my internal process revolved around the technical side of things—figuring out the best materials, gear, and process. Often revelations and improvements came out of failures. It’s been a constant learning curve. Tools change, materials are discontinued. So the biggest lessons there were:

Stay nimble. Designing a product means that available materials and tools will change. Keep your eye on the prize and know what you’re trying to do overall, rather than getting hung up on exactly how.

Invest in the right tools. Bootstrapping was critical to the early stages of my business. But I also held out longer than I should have on gear that helps me do my work.

Stay engaged. Keep trying to understand how your clients experience your product and service, and always work on how to solve more for them. Don’t get complacent.

The things that went wrong externally were often related to factors beyond my control, like shipping mishaps. Any problem that came up was mitigated by taking good care of my clients. I used the following principles to guide me through every situation:

Be clear. If a misunderstanding happens and causes a problem, assume it’s because you weren’t clear, understand why it happened, and adjust all future communication.

Manage expectations. Be very explicit about how you work, and why. Do exactly what you say you’re going to do, or exceed expectations.

Be generous. Once you’ve set up all the basic rules of engagement, there will be times when something goes wrong, anyway. Go above and beyond what you have to do and make people happy.

The most important thing I got right quickly was knowing what kind of business I was in. It allowed me to say yes to the right things and no to the wrong ones. For example, I decided right away that I was not in the custom design business. This was an important decision because my schedule didn’t allow for it. Just knowing that gave me a framework for what kind of work I could do, which set the stage for everything else. I referred people who wanted a custom design to other artists I respected who did do that kind of work.

What is the greatest thing about your new self-employed life?

The freedom to finally work on all the projects I’ve been scribbling about and thinking about for so long. The ability to take care of other aspects of my life besides work because I am no longer working two jobs. The feeling of total control over my time and my future.

What is your advice to someone who wants to “escape” from traditional work and start something like this?

Find what you love to do, and then do it, even if it doesn’t bring in money at first. Experiment on the side, experiment on the cheap. It’s the single most important concept to grasp if you are looking to build something from scratch.

What worries you?

Everything! I’m a chronic worrier. But there’s a bad way to worry, and a good way.

The bad way of worrying paralyzes you. You worry you won’t make the money side work, and it seems so overwhelming that you decide not to even try. I used to worry in this way, and did nothing.

The good way of worrying keeps you competitive, keeps you striving. For example, I still worry about making the money side work (especially now that I’ve thrown my weight into my own business completely). I still think, “What if all the work dries up? What if a competitor comes into the market that takes away my market share?” But I worry about it differently now. I worry about it by thinking ahead of the curve, recognizing what my strengths are and what I can do to mitigate that risk.

Now that you have more time to devote to the business, what’s next for New Ketubah and you? Do you plan to hire people or stay small? 

I plan to keep things small, but do big work. I’m energized by the idea of scaling talent, in the model Jonathan Fields describes as Simplicity Driven Entrepreneurship.

I have big plans for this breakout year of mine. Some of them have to do with New Ketubah, and some are new art and design projects. Among other things, DIY Ketubah just launched today! I am giving my most popular ketubah texts away for free as a download and inviting people to share the pieces they produce with it. I want to help accelerate the growth and exploration of this centuries-old tradition by enabling more people to make their own pieces and share their projects to inspire the community as a whole.

My weekly practice is still ongoing. I regularly post pieces that I make on a rolling basis—these include cards for people I care about, free desktop calendars for anyone to download, and my newest project: visual conversations with other artists.

I’ll also begin offering some of my design work for sale as prints, and will be rolling out a new collection of products that I am making to recast the expressions of Jewish identity I grew up with.

And that’s just the first half of the year! There are some super secret things brewing thereafter, and I hope some of the great people from AONC will join me in the journey.

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Congratulations to Tsilli!

If you like Tsilli’s work, you can join her newsletter here or follow her on Twitter here. You can also post any follow-up questions for her in this post.

And good luck to everyone else out there who is pursuing a dream of your own. I’ll look forward to hearing about your story one day.

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