#SheWearsThePants: Ilana Seid, Founder/CEO of Sunday Morning - on Alter Egos, Confidence in being Prepared, and Growth

Ilana Seid, New York City, Founder-CEO-mother-wife-activist-baker

What do you do - and what what drives you in your career as well as personal endeavors?

I am the Founder and CEO of Sunday-Morning.com. A mentor once told me that I should live in a way that makes my obituary worth reading and that has stayed with me. At the end of the day, we are all dead, so why not throw caution to the wind and live this one out? Also, I have a young son, Noah, and he is a source of energy for me - I know he is learning from me, and I want him to learn that we work hard to fulfill our dreams.

Ambition: What does ambition personally mean to you - what place does it have in your life? Do you think our culture perceives “ambition” to be a dirty word for women? Why or why not?

Ambition to me is a quest for growth. It is a nagging feeling that asks “What’s next? How can I grow? How can I optimize this one chance I have been given at life?” I think perhaps in the past ambition may have been perceived as a dirty word, but these days, there are so many successful and ambitious women that I feel like it is getting to be the norm. I certainly don’t have any reservations about being ambitious as a woman.

What does ‘having confidence’ mean to you - what place does it have in your life? How do you work on it?

Having confidence means being over-prepared and owning the situation. I really do a lot of preparation for important meetings, and practice delivery. As a result of the said practice, I am much more calm and collected and therefore confident in meetings. I am not sure if it is a result of age or experience (probably both), but whenever I find myself feeling doubtful, I have an alter-ego that kicks in and her war chant is “if you were a man, you wouldn’t doubt yourself.” I am hyper aware of the programming that we get as women, and I actively try to change how I feel when I am not feeling so confident.

Goals: Please share one of your current, important goals (can be personal or work-related). Why is this a goal and how did you realize it was something that you wanted to work on? What’s your plan for achieving it?

Goals: Raising a seed round of funding for Sunday-morning.com in the next year. I sold an apartment I owned to bootstrap my business and bring it to life, and now I need help and money to see it grow and flourish into a real (and hopefully huge) business. I don’t want a hobby or a lifestyle business; I want to build a large and successful company, and this clarity has helped me realize I need to raise money for the next phase of growth. I am actively networking and building up my pitch deck in anticipation of starting to fundraise.

What do you do if you are having a hard time defining goals? How do you stay motivated to fulfill your goals and sense of ambition, and what do you do when you get stuck?

One exercise I like to do is create a 5 year life plan and put it on paper, much like a business plan. Truthfully, I am having a hard time defining business goals now since it’s my first business, so I am trying an executive coach to see if that helps me define things and keep me on track. Hiring people to help me with Sunday Morning really kicked me into gear. I was nonchalantly working on it for a while but I’d get distracted and work wouldn’t get done. But now that I have to pay people and want to keep them engaged and motivated, I really work harder and stay focused.

What is your outfit when you really have to get shi*t done?

I work mainly online, so it's fairly comfortable - a shirt or button down shirt, jeans, leggings, or black pants, some nice sandals or sneakers.

What is one fashion tip / hack you swear by for a quick or on-the-go change?

I am afraid it's the ubiquitous New Yorker all-black outfit. I can change shoes to dress up or down (neutral pumps for a meeting but gem toned heels for a party after), but it is a go-to when I don’t have time to plan.

What is your process - or what are you guidelines - when choosing to buy something new for your wardrobe?

Will I wear this in 5 years? Is this life-proof i.e. can I carry around a toddler in it? Am I comfortable in this? Does this make me feel [powerful, cozy, confident, elegant, sexy]? I am generally pretty practical about my wardrobe but there are moments where I allow myself to experiment a bit. For instance, I am considering purchasing a leather dress- typically not something that fits the usual checklist, but I could see it boosting my confidence as I walk into a fundraising meeting, so it’s on my maybe list. I’m 90% certain though that it will be too high-maintenance for me, and I’ll just go back to a black silk-T with black trousers and nude pumps.

What activities do you do outside of your full-time gig (whether that’s work, parenting or something else)? How does it bring balance to your life? How does it make you more successful in your full-time gig?

I try very very hard to not work on weekends. Truthfully, I burned myself out working all the time for 6 years as an investment banker, and burn-out takes a long while to recover from. So now I am very conscious of putting boundaries on work and allowing time for rest and for play. I will sometimes cheat and work while my toddler naps, but otherwise, Saturday and Sunday are for me-time and family, and they always involve brunch and time outside. I love hiking and being in the woods, so we try to drive out of the city regularly just to have a walk. I also have a standing date night once a week with my husband - we’ll usually go out to see some theatre or a movie, and try a new restaurant. We are huge foodies and this time to connect sans-baby and enjoy something we both love is always something that balances out my week.