Entrepreneurial Dreaming On Such a Winters Day

Jessica Sun Lee spent the last ten years as an interactive/digital designer in the Boston area.  While she had great success in the field, she started to feel disconnected to her work and craved the creativity and passion she felt for creating tangible art that you could touch, feel and connect with physically.

Cindy Meltzer worked as a director of social media for a Boston-based company for several years, spearheading a robust social media campaign for them and revitalizing their brand.  While she enjoyed her career, she longed to do more strategic work with a wider variety of brands, and as a working mother desired the flexibility to make managing family life easier.

Do these stories sound familiar to you?  Do you find yourself dreaming in the middle of the day about how you can turn your hobby or passion into a real job, possibly even a thriving business?

Like Jessica and Cindy, you may feel insecurity and doubt about your future success as an entrepreneur; or you may just not know where to start.   Check out the below tips and learn from those who have ventured before you as you search for your inner entrepreneurial spirit.


Most of the insecurity with starting your own business lies with the demand for your product. What if no one wants to buy what I am selling? Both Meltzer (now the principal of her social media consultancy, The Social Craft) and Sun Lee (the owner and creator of Love on the Blocks) were initially unsure of what the demand would be for their craft.  What is interesting is that for both subjects, there was an immediate enthusiastic response from the public.  Meltzer said she became secure in her business idea after she sent out an initial launch email and received overwhelmingly positive feedback almost instantly.  Sun Lee started selling work at a local art market and was amazed at how quickly the public connected with her work.

entrepreneurial dreaming

The response from the public for these two entrepreneurs isn’t surprising.  When a person is creating something that they deeply connect with and feel passionate about, their passion becomes contagious.  It is important to remember that when honing your brand, passion is felt not just seen or read.


Many people fear that once they start a business centered on their passion and have to work at it every single day, they will grow to dislike the thing that they once thought they loved. When we asked Meltzer and Sun Lee whether or not this was true, they each gave a resounding no. They both focused their initial plans on streamlining their craft so that it fell directly in line with what they felt the most passionate about.  The work is enjoyable because they truly love it.  One of the benefits I’ve found of having my own business is being able to focus on exactly what I want (and love) to do professionally,” says Meltzer.


When aspiring business owners first start out, some of them are at a loss as to where to begin. They know they love their craft, but how do they make it into a business?  Sun Lee suggests learning from other people’s mistakes: “Find people who are succeeding at your business already and learn from their triumphs and mistakes. Put money aside. Research your equipment. Know that it will be a process and accept that you aren’t going to get it right off the bat. You aren’t going to be an overnight success. It takes work.

Meltzer, being a branding guru, suggests starting off with a real defined brand definition.  “I’ve had people hand me print-it-yourself business cards and even slips of paper, saying they ‘haven’t gotten their cards yet’.  You need to look polished right out of the gate if you want people to take you seriously,” she recommends.


Many independent business owners who are working from home find that as a result of being so isolated they have become separated from their community, and thus stagnant the growth of their business. Meltzer suggests a few ways to fix this: “Create a support network – whether that be online, at a coworking space or even a weekly coffee date. One of the things I did early on was create a Facebook group of like-minded professionals with whom I could share strategies, ask questions and get advice. It’s proven to be a valuable resource in the absence of a traditional office environment.”

entrepreneurial dreaming

 We certainly see the rewards of this at Workbar through the interactions we see between our members.  Building a community around yourself can really help keep you focused, and help you troubleshoot any challenges.  Sun Lee agrees that “personal connections are more important for sales than the internet. Go out and make friends; go to events and market; be part of the community.”


Many people fear that starting their own business means they have to kiss their lives (and even their loved ones) goodbye.  The best way to stop your business from becoming life consuming is to set your own limitations. Sun Lee spends half her 8 hour day on maintaining and updating her website and the other half on creating work. She commits to keeping the evenings free to write music with her band and take care of her puppy.

Professional resources are a must and there are great systems to help you stay organized.  Cindy is able to be a mom and still post regular content by using online apps to maintain her Twitter feed so that she doesn’t have to do it in real time.

If anything, working for yourself allows you to create your own schedule without having to worry if your coworkers will have conflicts.  “There’s nothing like the flexibility of working for yourself. It’s like a huge burden was lifted when I realized I don’t need to worry about coverage for school vacations or when my kids are home sick from school.  I also like the professional flexibility to initiate [only the] projects I feel passionate about,” says Meltzer.

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Naturally starting your own business costs money.  Websites need to be created and maintained; products need to be shipped to customers; services need to be valued and rendered.  There are slow periods where it seems like everyone on the earth is no longer interested. The ‘feast or famine’ nature of independent consulting can be tough” says Meltzer.  “December was so slow I questioned whether I should even be doing what I am doing. Then January exploded. You have to be willing to ride out the slow periods and measure your success longer term.  But that can be difficult financially.”

In order to achieve long-term success, you will have to plan ahead financially.  Save more money than you think you will need and have a backup plan.  Searching for funding is a good step further down the road, but being in control of your own financial future is part of the pleasure of owning your own business.  Losing a regular paycheck is scary and causes a great deal of uncertainty, but the flexibility of managing your own finances can be very rewarding.  Besides, it’s not about the money, it’s about your passion, remember? The money is just a fantastic side effect of feeling fulfilled by doing what you love.  So stop dreaming and start doing!  The world is full of opportunity and it is now your turn to launch a successful, passion-filled new venture.


About Workbar:

Workbar operates coworking locations throughout greater Boston (Boston Back Bay, Boston South Station, Burlington, Cambridge, Arlington, Brighton, Danvers, Norwood, Salem) and several other partner locations throughout the state. Want to keep up with the world of Workbar? Subscribe to our mailing list for the most up-to-date information about our upcoming events and community news. You can also follow us on Instagram, Facebook, LinkedIn and Twitter.

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