NEW YORK, NEW YAWK: So Nice, I’ve Lived Here Twice.

From Issue 110 — Author Awakening

My journey back to the Big Apple and starting a business from scratch.

I love this city. I know a lot of people do. For me, it’s a different kind of love.

I first moved here in 2012. Before the Freedom Tower was erected, but after 9-11. I lived downtown in the Financial District and attended a training program in television advertising.

The energy on the streets was much needed after a rough recession that hit my home of Detroit with the fallout of the auto industry which shook the Motor City.

I loved this city so much. In the 11 years that passed since my return, all I could think about was coming back. I have lived in 14 cities, five states, and three New York City neighborhoods from the time I turned 18. None can compare to this city.

So much has changed, and at the same time, much has stayed exactly the way I always remembered it. The nods on the street, the taste of a fresh bagel and schmear, coffee from the food truck.

These days, on the Upper East Side, you wouldn’t actually know I live in a bustling city. It’s quiet. People take their dogs and kids around the block and I routinely run into neighbors on the street.

They call the Financial District FiDi now and advertising is AdTech. People aren’t wearing suits to the office anymore. Instead, it’s unusual if they go in a few days a week in business casual.

Many of my friends have left the city. Native New Yorkers who grew up here. They left during the pandemic and have yet to return. Some left the country. Others live across the country.

My second stint in the city has been a transformation in so many ways. New friends and neighbors, a plethora of experience traveling, but also, a new business.

When I returned here, I very much looked forward to slowing down. I had ventured across the country after four years out West. I opened myself up professionally by breaking into the software tech space. I survived the CoOp process (if you know, you know).

The joke’s on me… There has been nothing slow about the past two years.

The highs have been high, the lows low. Ramping up a business during a time of uncertainty and change has not been for the faint of heart.

As I reflect on my journey starting a consulting business, there is so much I want to share in hopes I may help someone else. Someone thinking about starting their own venture. It doesn’t need to be a business, maybe it’s a big personal decision.

  • This will be the hardest and most rewarding experience of your life. When you understand this, you can persevere.
  • Never take NO from someone who can’t tell you YES. If you cannot influence key decision makers, it will be really tough to get the deal done. This can be as true in sales or career pivot as it is in business ownership.
  • Embrace rejection. Every person you meet will teach you something. You will leave them better than you found them too. Not every interaction will result in business, but it will move you forward.
  • Get comfortable putting yourself out there. I’ve met more than 300 people since I started my business.
  • Learn the landscape. Things are changing. Don’t leave yourself behind. Learn all the things. It’s an exciting world out there! Even that AI stuff, it’s a lot of fun!
  • Partner with people quickly. This is how big projects and collaboration happen. You are only as good as your tribe. They will get you through challenges and provide solutions.
  • The highs are high, but the lows can be really low. I had four deals fall through in an hour on the same day. I called an experienced peer consultant and her advice was definitive, “This is when people throw the towel in, don’t quit, keep going.” The following week, I closed four pieces of business.
  • You are everything. Some days I feel like a mechanic with a broken car. I am behind on updating my social media and website, because most days I am entrenched in helping my clients with these things. It’s tough. Get experts to help with the things you are not familiar with.
  • You will underestimate how long things take at the start. It takes nine months to have a baby. Don’t expect to birth a business in less time.
  • After the first year, things do get easier. You find a flow.
  • You are your reputation. Do what you say you’re going to do. Respond to every single email, call, and LinkedIn message.
  • Do the easy things to make the hard things easy. Take people to lunch to learn the true nature of their business problems.
  • Have a tribe. Solopreneurship is extremely lonely. Not everyone will support you. People you love will vehemently oppose your decision to start a business. They will tell you about all the things that can go wrong. It’s important to minimize their involvement in your affairs and keep supporters close.
  • Warren Buffett said, “The most important decision you make is who you marry.” Truer words were never spoken. I am so grateful to my husband, Brad. He has celebrated my wins and helped me stay true to myself during some of the lows. I am so grateful to him. Find yourself a Brad.

It took me all of the last two years for me to see things the way that I describe, but starting a business has been such an incredible experience, in all its messiness. It is the accomplishment I am most proud of. When you build something from scratch, you realize it can never be taken from you, and the decade of learning you squeeze into a year can never be replaced. You can never learn this stuff in a classroom.

So, as the new year is upon us, be open to trying something new. It’s going to be hard, but trust me when I tell you, it will be worth it.

Jackie Giammara
Jackie Giammarahttp://www.five3consulting.com
Jackie Giammara is a business optimization and growth consultant. She specializes in client success, process excellence, and operational restructures. Jackie lives in New York City with her husband and their three French bulldogs.

Check This Out

Wales Bonner and the Reconstruction of Luxury’s Visual Language

Grace Wales Bonner's appointment as artistic director of Hermès menswear represents a fundamental philosophical reorientation of what luxury fashion can articulate. The truly radical dimension isn't just about who she is, but about what she brings, an entirely different epistemological framework, one that treats fashion as a site of rigorous intellectual inquiry rather than a commercial spectacle. What makes this appointment significant is how it reframes the very concept of "heritage" at one of fashion's most conservative institutions. Hermès has mastered the art of selling a particular kind of heritage, carefully preserving the traditions of saddle-making in silk scarves and leather goods. Wales Bonner offers something different: heritage as multiplicity, as the complex layering of influences that characterizes diasporic experience. Her work suggests that tradition isn't a singular through-line but a chorus, and how luxury can be the vehicle for expressing these layered, sometimes contradictory cultural genealogies.

You, Me and EOP

My life and career have unfolded at the intersections: my Cuban American heritage and New York upbringing, global cultural traditions and American artistic forms, simultaneously inhabiting the creative and the strategic. I’ve always been drawn to collaboration — the quiet work of listening deeply, helping artists articulate what they want to make, and then building the structure, the partnerships, and the resources that allow those ideas to flourish.

A Portfolio House Folds in Silence.

It's loud, or rather, it was always loud. It was a haven for those in the world of print, a rite of passage. It was the House of Portfolios NYC, Inc. I was too late. My timing has never been great. It has always seemed to allude me. In music school, of which I spent 8 years studying and then some, taught me that keeping time in a measured manner was paramount. For me, the sound of silence excited or held anticipation for the next passage. Solos that floated through my clarinets seemed to bend time over accompanying piano, or orchestra, but playing together as a body at times felt constricting.

All Categories

LEAVE A REPLY

Please enter your comment!
Please enter your name here