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.


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.


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.


    Subscribe now and you’ll get the best posts of all time.


    • Etsuko says:

      Reading your blog post on Monday morning has become a part of my routine! It’s such a great start of a day and a week!

      Thank you for bringing her interview out to the world! It was most interesting and I could relate to so much of what she is saying, because I just did the same thing! I quit my day job at the end of January to strike on my own. I love your questions also. I particularly liked what she said about early troubles:

      “But with determination and a positive attitude, nothing has been insurmountable”. I’ll keep that in mind when I encounter many more of mine.

      Have a wonderful week!

    • Jonathan Frei says:

      Great story about a careful entrepreneur. It gives hope to the more risk averse among us…

    • Susan says:

      Love it! What an inspiring story and so unique. Great to hear that entrepreneurs can be pragmatic risk takers and do so on their own schedule and needs.

    • jon setzen says:

      Full disclosure: I’ve known Tsilli for years. She is one of my most talented friends. This has been a long-time coming for her and it’s inspiring to see someone do something they not only love but also believe in. Go get ’em Pines.

    • soultravelers3 says:

      Congrats to Tsilli! Great story!

      My personality type thrives on risk and that has served me well in a lifetime of entrepreneurship, but the conservative and cautious part is also deeply needed.

    • Greg Blencoe says:

      Congrats, Tsilli! It’s wonderful to hear her story about starting her own company and now working full-time on it.

      One of the main points I took from the interview was the importance of making mistakes (and learning from them) early in the process. In any new endeavor, there is really no way of knowing exactly the way things are going to turn out. There are going to be missteps along the way.

      But Tsilli seemed to limit her downside by making the mistakes and optimizing her approach early on in the process. And now she can take the company to the next level, because she knows what she is doing.

      Furthermore, here is one comment that Chris made that stood out to me:

      “Entrepreneurs are often thought of as embracing risk—but I think this is a bit overrated.”

      I completely agree with this statement. Like Tsilli, I think a lot of successful entrepreneurs are very careful about the decisions they make. I also think many entrepreneurs are so self-confident that they don’t see lots of risk.

    • Roy Jones says:

      great success story and an inspiration to others to follow a dream even after many years doing the same thing

    • Avil Beckford says:

      Thanks for sharing the interview. Contrary to what many think, most entrepreneurs are not risk takers, but they take calculated risks to minimize losses. It’s great to see Tsilli’s transition from working full-time for someone to working full-time for herself.

      One of the things I liked about the interview is her sharing about things that went wrong because we can learn so much this way. No matter how we plan and take all the precautions in the world, things will always go wrong but what is important is how we react when things do go wrong.

    • Devin says:

      Great information and great lists, Chris.

      I have always been a freelancer in order to pursue things I love: travel, writing, music. It has always been such a gray area to crack the code to full-time entrepreneur. I am much further along than I was say six months ago, which I am happy about, but still a difficult process.

      I am grateful when I hear about stories from people who have made the leap.

    • Nathan says:

      Wonderful story to start off the week – full of very practical advice, along with the anxiety/worry we all have – congrats to Tsilli on her adventure!

      She is absolutely right: find what you love to do and do it, even if it brings in no money at first. If you are really good at it, and really love it, success will follow.

    • Catherine Chang says:

      I love reading about people’s experiences with starting their own small businesses. Hopefully I will be joining their ranks in the near future. I totally agree with her thoughts about worrying: “The good way of worrying keeps you competitive, keeps you striving.” I always tell myself and other people not to settle or stay content for too long because it’s easy to lose the drive to continue to progress. Worrying can be stressful, but it spurs people with drive and ambition to change the situation for the better.

    • Mars Dorian says:

      What a refreshing interview.

      And what a unique business. You’ve just expanded my horizon once again. She’s very likeable, and her business insights are “demasiado interesante.”
      It’s always inspiring for someone to finally make the leap, despite the overall risk. To hell with the uber-caution, just do it 🙂

    • Patrenia says:

      WOW! Congrats Tsilli. What a major accomplishment. It’s so inspiring to see others set goals and follow their dreams!

    • Daniel Sroka says:

      As a fellow artist who also launched a ketubah business, I have a great deal of respect for Tisilli and her work. Excellent interview, really illustrated a lot of what I also went through when I transitioned from being a creative director to being a artist/entrepreneur.

      It’s tremendously challenging to work for yourself, but that challenge is exactly what makes it worthwhile. The work I did in my corporate days was often hard, but it rarely rarely challenged me the way my own little business does. My corporate job never pushed me to my limits, or encouraged me rise to a new level of achievement. As hard as I worked, I always felt like I was only using half of my abilities, at best.

      But working on my own, for all of its stress and anxiety, always asks more of me than I thought I could ever give. It always pushes me to use every skill I have, and constantly learn new ones. It is never satisfied with letting me coast along at half-speed, but constantly forces me to be, entirely 100% me.

    • MatCoes says:

      Great profile. More like this, please!

    • Tyler Tervooren says:

      Go Tsilli! I’ve got one of her calendars set as my desktop background right now. I love it!

      Like others mentioned, It’s interesting to hear about the other side of the aisle with the very careful and risk averse entrepreneur.

      I really respect both approaches, but know for myself that I’d never get past the dreaming stage if I continued trying to work it out after hours. When I got laid off, I tore up my resume and jumped in head first.

      I’m actually starting a writing project soon based on improving life though calculated risks. I’d love to chat with any interested AONC readers about it on twitter (linked above).

    • Thursday Bram says:

      What a great story! And perfectly timed, at least for me — my cousin’s right in the middle of trying to figure out her ketubah and everything else for her wedding.

    • Alicia says:

      People like Tsilli will turn the economy around. It all starts with the idea and passion of just one person. Great post!

    • teevee says:

      It was awesome to read the thought process of someone that made the leap as well. It is only appropriate that I read this on the one year anniversary of my own leap. I love reading of others doing the same.

      Thank you,

    • Meg says:

      It’s great to know there are successful, cautious entrepreneurs out there. 🙂 I’m pretty cautious myself, but it’s funny since I have no real reason to be so. (At the moment, my income is wholly optional.)

      With everyone saying follow your passion, I will finally be listening and spending at least half this year trying to make freelancing work for me. I’m very excited to take the chance, if not quite nervous at the thought. We’ll see what I manage to accomplish if I throw caution to the wind and throw myself into making it work. 😛

    • Daniel says:

      Congrats! I experienced many of the same things when I quite my corporate job 2 years ago. The advice of staying engaged is right on. Something I still struggle with myself.

      I hope 2010 is very successful!

    • Tsilli Pines says:

      Hello everyone! Thanks so much for all the well wishes and thoughtful comments.

      Learning how to “fail forward” has been one of the most important lessons of all. It’s surprising how much you stand in your own way, thinking that things have to be just so. So true that the earlier you make mistakes, the more quickly you can move beyond them.

      I also didn’t realize at first how far good intentions can take you. I was scared of not being able to pull things off. I learned as I went that even when things did go sideways, trying your best to make good takes you a long way. Of course you should also have a strong sense of your bottom line, but respecting your clients and doing what you can to do right by them is central.

      I’m really happy to connect with you all here — thanks so much for your interest!

    • marianney says:

      i love reading about how others do this. it’s inspirational and lets me know it can be done. thanks for sharing!

    • Laura Lee Bloor says:

      Congratulations, Tsilli! I’m so glad to hear that all your hard work and passion is paying off! As you can see, you’re a huge inspiration to many of us.

      One question: What’s your strategy for finding new clients?

    • monica moran says:

      i love reading articles like this: creative folks who manage to leave their day jobs by doing what they love – keep more of these stories coming Chris!! they are SO inspiring for me as i begin my own journey to self-employment =-)

      thank you, Tsilli, for sharing your experiences with everyone here at AONC – there’s a lot to learn from in this interview!

    • Tsilli Pines says:

      Hi Laura –

      Many of my clients are actually searching pretty intensely for me, believe it or not. I’ve built my business around gauging demand and meeting it. The power of a niche market / skill-set is that people generally want to connect with you as much as you want to connect with them!

      My two top strategies for connecting with clients are:

      1. Make it as easy as possible for people to find me when they are looking for something I do (this is where the niche market comes in–if you’re competing with a lot of people who do what you do, it’s harder).

      2. Take excellent care of clients so that they are super happy. This leads to referrals, and generally makes doing business more fun.

      Thanks again to everyone for the enthusiasm!

    • Cheryl Paris says:

      Thanks for posting such a great story. Congratulations to Tsilli on going great and working full time something she loves.
      It’s great story to learn and act from. All the points highlighted are “words of wisdom”.

    • Phil says:

      Congratulations Tsilli – it is beautiful to hear about someone making a living from their passion. I love that it took years of hard work and planning to make it happen. I take my hat off to you for sticking at it and having the dedication to make it work.

    • Marc Winitz says:

      Hi Tsilli – I just love your story and thoughts. Hats off to you and your commitment to making this happen for yourself.

    • Kate says:

      What an awesome article!

      I’ll admit that I am particularly inclined to lovve it because of our own ketubah-hunting issues, but it’s also wonderful to hear about someone striking out on her own!

    • Tsilli Pines says:

      Thank you all for the love you keep sending my way!

    • Adrienne says:

      Wow – great interview. I am working hard to be able to quit my job soon as well. It’s always great to see someone who’s done it – to remind myself that it is possible!!

    • chacha1 says:

      Great article. I especially appreciate the “risk-management” approach Tsilli has taken. I’m trying to do something similar …

      With the goal of leaving full-time office work within ten years, I started by studying for a high-quality personal-training certification. Not long after finishing that, and right at the time I realized I needed to leave a toxic job, an opportunity opened up to take a ballroom dance teacher-training course. Since I’ve been a happy dancer for over a decade, this seemed ideal, and I did the course while working full-time at a new job.

      Just as I was finishing up the teaching course, I got laid off. I was able to pick up some extra income from teaching during the months it took me to find a new full-time job.

      I have been building my reputation in the dance world from the beginning, but now a lot of people know me as a teacher and I’m regularly requested to teach at a local social dance club. So letting the “road appear beneath my feet” has worked!

    • Shannon says:

      How exciting to come across this interview. Tsilli made my ketubah and I absolutely adore it. I searched for a long time – there is nothing else like it out there. She is so talented. As a designer aspiring to have my own business venture in the future, I loved reading more about her success!

    • Marie says:

      Thank you for this story. So similar to my journey. I haven’t taken the leap yet, but very soon. I am half scared out of my mind and half incredibly excited and elated. I have worked from the bottom with nothing and learned everything the hard way.

      I develop websites and some print media. The most difficult thing at first was finding clients. I find that if I work insanely hard, and focus a ton of my energy on being an amazing person then the people sort of just find me. This isn’t to say that I haven’t given a lot of my time away, and that can be difficult. But I give it away to the people that mean a lot to me already. I share my talent with them in a way they find meaningful. Word of mouth spreads quickly that way. I love this blog and will surely be back often!

    • Writer's Coin says:

      Congrats Tsilli! This is an awesome story. One thing that jumped out at me was your answer for a “first step.” You said to find what you love and go from there. But there’s a lot of debate about whether or not that’s the best way to start. What if what you love doesn’t monetize well? Or is it about being creative enough to find a way rather than starting off with something you know can be monetized from the start?

    • marta says:

      Well done Tsilli! it’s always inspiring to see young entrepreneur pursuing their dream and passion and making a profession out of it. very remarkable.

      I just hope to have the courage to pursue my dream of traveler blogger too which for now is only a passion, soon i would have to face the reality to go back to the 9-5 job

    • Jennifer Moore says:

      Tsilli, you are an inspiration! I love the idea of “do what you love and the money will follow.” Reading success stories like yours lets me know that it CAN be done.

      I am doing what I love on the side right now and have high hopes of making it ALL that I do in the future.

      …And also, thank you for introducing me to the concept of the ketubah. I did not know about them. You learn something new every day.

    • Tsilli Pines says:

      Shannon! Hi! Your kind words mean so much. I feel lucky to contribute a small part to such a happy moment in a couple’s life, and to make something they will enjoy in their homes for many years to come. It’s an honor and a privilege!

      To everyone who is building toward their own dream: you can do it. I was such a skeptic before, and it’s been transformative to find a way. Not everything has worked along the way, and I’ve taken really slow steps that are calibrated to my cautious nature.

      But slowly, slowly, things have come together. As Chris often says, people tend to overestimate what they can do in a day, and underestimate what they can do in a year. Keep at it and you will see progress!

    • Tsilli Pines says:

      Marie has brought up something that a lot of designers starting out need to know.

      There are good ways and bad ways to do free work. Spec work (where you pitch a design for free in the hopes of getting paid) is a scourge, but strategic free work for cool people doing cool things is actually super smart.

      For example, my friend Jon Setzen, who commented above, did awesome posters for a music venue in Brooklyn when he started out. He became known for being the rock star that he is, and it got him some huge accounts (you can see his work here).

      To all the designers getting going: build your portfolio by connecting with small businesses that need help, and do something great for them. Do the kind of work you eventually want to get paid for. People will take notice, and you’ll learn the ropes.

    • Tsilli Pines says:

      Writer’s coin raises a great point about the labor of love question. There are several ways it can go wrong:

      1. You can’t monetize it.
      2. You end up hating the thing you thought you loved because it’s your business.

      For some people, it’s better to figure out a hustle that brings in money so that they can continue doing what they love without commercial pressure. That’s a totally legitimate way to go.

      I sort of do this, myself, in that I make design products and do client work for money, and then I also do totally non-commercial art projects for the love of it. The cool thing about doing things that are related in that way is that one thing adds value to the other. I talk a bit more about this in this conversation that’s going on at Get Rich Slowly.

      Whatever you choose to try: test early, test often. Reading Pam Slim and Tim Ferriss gave me a lot of ideas for how to think about this.

    • Hema says:

      Congrats Tsilli! What an inspiring article. I plan to try to apply some of her tips to my own business of handmade scrapbooks for Bar/Bat Mitzvahs and Judaic cards.

    • Laura says:

      Great niche business idea- congratulations on your new independence from the 9 to 5!

    • David says:

      Congrats! and great business idea.

    Your comments are welcome! Please be nice and use your real name.

    If you have a website, include it in the website field (not in the text of the comment).

    Want to see your photo in the comments? Visit to get one.