Taking on Entrepreneurship: Leaving a Steady Job and Building “Community Connect”

Community Connect Consulting is a Chicago-based project management consulting company providing a consolidated approach to creating sustainable and dynamic organizations. Led by Becky Adelberg, a passionate connector and shining star of the Jewish non-profit world in Chicagoland, Community Connect Consulting will help you develop effective programming, foster community relationships and establish a long-term vision for your organization.

Following years working in the Jewish non-profit sector, Becky decided to fully devote her time to her own venture and helping other organizations thrive. Her clients include companies at all stages of growth – from the smallest start-ups to the biggest corporations. We talked to Becky about what it feels like to leave the safe waters of regular paychecks and to head towards the insecure albeit exciting unknown.

  1. How did you know when was the right time to take the leap and seriously commit yourself to your business?

I had the idea several years ago but then I was busy running an entrepreneurship fellowship and teaching entrepreneurship, so I didn’t have time to work on my own venture. Then, in January 2017, I did a soft launch of the business and saw that I was getting a few clients without marketing myself. In November 2017 I was presented with the opportunity to have a part-time job, which would have allowed me to focus on my business for the rest of time. Following my experience with launching a non-profit a long time before, coupled with my experience teaching entrepreneurship, I decided that I finally wanted to live this as well.

  1. What are the major considerations in making such a decision – leaving a steady job and devoting your time to building a business?

I think you need to be mentally ready and you need to know what kind of entrepreneur you are – there are some who go all in and there are some who do it part-time in addition to their day jobs. I always knew I was a combination of both, I needed to have some kind of consistent income while working on my business.

The considerations are that when you are on a contract, there is no guarantee, it is like a shift in your mindset. You have to become better at time management because your time is your own. At the same time you have to balance. I have always believed in work-life balance but when you are passionate about your venture, you can burn out easily so you need to take care of your time so that you don’t take it from the other areas of your life. Now I feel healthiest I have been so far but it constantly a work in progress.

You also have to set boundaries for yourselves – I could work until midnight but you really need to create a lifestyle that you want and you need to realize that there are going to be ups and downs to everything you do. Ask for support and try to meet with other people that do different things so that you are not silo-ed. 

  1. Were you consciously preparing for this decision ahead of time? Or did the stars align?

It was a combination of both. I had planned this for a long time, I had a vision and started putting pieces in place and then the stars aligned for this to happen. Then it was like …. that’s when you see that you have free will … but you have to make a decision so I took a chance. If it had happened earlier, I might not have been ready for this but I was ready now.

  1. And how do you know that you are ready for it?

When you weigh the pros and cons – but, there should be some scariness to it. It feels exciting and you get excited thinking about it and that’s what life is about, you need to take calculated risks 

  1. What single piece of advice would you give to someone who is considering leaving a permanent job to start their own company?

It has to be something that you want to work on all the time. If you don’t feel that excited, then maybe you should not be considering doing it full time. Balancing is very important because the work never stops. Be open to things shifting. In fact, they should be shifting because this means that your business is growing and moving. My business model has shifted several times, and even over the past year, I have pivoted several times. 

  1. What motivates you?

My dreams. Community. Passionate people making a change for the better.  Achieving things I never thought were possible.


 Becky Adelberg

Becky is the Founder of Community Connect Consulting.  She is highly experienced at business development and project management having launched two successful companies.  In addition, she has worked with dozens of organizations to expand their reach through the execution of large community events, strategic partnerships, volunteer management, leadership development, fundraising and travel abroad initiatives.  Becky has also overseen a social entrepreneurship program for four years, taught entrepreneurship to new immigrants and coordinated a teen summer program focused on entrepreneurship, while in turn, helping over a hundred entrepreneurs gain the skills valuable to apply to their own businesses. She is a frequent lecturer, serves as the Chicago coordinator for Reboot, a mentor at 1871 Chicago, a voice over artist and a meditation instructor.

She holds a BA in Communications from the University of Kansas, an MA in Jewish Studies & Education, from Siegal College of Jewish Studies and a Certificate in Jewish Leadership from Northwestern and Spertus Institute of Jewish Learning.  She has a track record for being a community connector, who thinks of and executes fresh, innovative and creative solutions to maximize a business mission and reach. In her free time, you can find her traveling, spending time in nature, doing yoga, writing and photography.