A Day In The Life of a Post-Breakup Concierge CEO
CEO & CoFounder, Onward: A Post-Breakup Concierge Service
Lindsay is the CEO & Co-Founder of Onward working primarily on creative strategy, member on-boarding, and relocation management.
Lindsay woke up to a slew of early morning group texts from her good friends, Corrie and Gemma. They’re such good friends that Lindsay said they’ve been on one long group text with since they all moved to the city in 2007 after graduating from Northwestern University.
They’ve managed and mediated each other’s personal and professional lives for over a decade. The tea in the group chat this morning was Gemma managing sleep regression from her six-month-old son. Corrie, who’s a mother of a one-year-old among other accomplishments, was offering tips and also commiserating.
All of this happened between 5AM and 6AM, so Lindsay was catching up on the chain while also perusing the Skimm for a quick news briefing—a great distillation of current events. She then dove into the New York Times’ trending top stories and arts section, hit a heated yoga class, grabbed a Starbucks, and was out the door she was.
Lindsay was en route from Brooklyn to New Brunswick, NJ for a board meeting, so her commute was a combo platter of the subway and good-ole NJ Transit.
During prime-travel time, it’s usually hard to get any work done—there’s usually not much room to sit, let alone whip up your laptop. Lindsay said she likes to make the most of the time she’s taking traveling. If, keyword, if cell service cooperates, she’ll make calls to clients, Onward partners or Onward team members to touch base or iron out details.
On this day specifically, Lindsay got into a car of the train that was completely empty and thought to herself, “score! when does this ever happen?!” So, she started taking calls not thinking anything of it. The empty car bliss didn’t last long because a bunch of people got on at the next stop and Lindsay was quickly informed the car she was in was the quiet car. She put her phone away and thought to herself, “I didn’t even know NJ Transit has a quiet car now, that’s so Amtrack!” Oh well, working in-transit makes her carsick anyway.
This particular morning, Lindsay met with fellow board members as well as faculty members of the Bloustein School for Planning and Public Policy at Rutgers University.
Her dad, who passed away in 2018, was a director and professor at the school and an urban planner for 45 years. Rather than do a memorial, her family thought it would be more meaningful to adapt an annual lecture series focused on innovative ideas in the field, specifically in regards to land use, city planning and fair housing.
In this particular meeting, they discussed the second annual lecture which is in two months, as well as other developments at the school. Lindsay shared, “it’s a far cry from the world of breakups, but I’m proud to continue to serve and support my dad’s great work.”
Her role in these meetings is two-fold. She’s making sure her father’s legacy and values are preserved in good taste. Lindsay’s also offering her event production skills as a former Broadway producer to put on the best lecture series possible.
Lindsay is an only child. Both of her parents passed away and when asked about the role her family plays in her career, she said, “my parents were champions of mine.” Growing up, Lindsay always had support from her family to develop her interests with no judgment (but some eyebrows were raised here and there ?).
Her father was into jazz music and would bring her along to jazz festivals all over the world, which she thinks influenced her decision to go into the theater. Her mother was a divorce attorney, hence the breakup concierge! Without her parents’ influence and support, she believes she wouldn’t be where she is today.
“There was this sense of closeness in my family where it felt like we were all the same.”
Lindsay was having a working lunch in New Brunswick, NJ, using the time to follow-up on some Onward member inquiries and issues. One of those issues included coordinating a member move for later that week, which involved transitioning ConEd and Verizon services for a member. Then, she moved on to prepping a road map for a new intake from the day before. Speaking of member inquiries and road maps, who are the potential clients going to Onward and how does this process start? Potential clients come from all stages of the breakup phase from…
- People thinking about pulling the trigger & looking for advice on how to proceed.
- People who have recently gotten out of a serious relationship.
- People who are inquiring about services for a friend or family member.
Lindsay said the on-boarding process for an Onward member starts with a short survey followed by a free, 15-minute consultation call that she conducts and manages. In these calls, Lindsay’s trying to figure out how Onward can help with by trying to suss out what services he or she needs to determine which package fits best: the 10-day reboot, the 30-day recharge, or the 3-month recalibrate package. For example, not all clients will need to hire a dog-walker or belong to a new yoga studio. (Fun fact: when Onward first launched, the co-founders thought the clients would be predominately women. Turns out, Onward has a good mix of male and female clients!)
“Just as no two romantic relationships are the same, no two romantic breakups are the same.”
In other words, This 15-minute phone consultation is what Lindsay calls, “a road-mapping session,” to set up clients to navigate this tough time in their lives with their best foot forward. From this call, Lindsay puts together a road-map for clients from start to finish what needs to go down, when, where and how so that all the client needs to do is approve, sign the check and put it into motion themselves or let Onward take the reigns. Lindsay said the 10-day package is most popular because it really focuses on the relocation part. For example, what area of NYC do you want to move to? What type of living situation can you afford? Do you want a roommate? Things like that. The 30-day package focuses on relocation and logistics and the 3-month package focuses on everything mentioned with more curated recommendations, facilitation, and weekly check-ins.
“We’re kind of their trail guide to their new life.”
Now that you have the context you need, back to the day! Lindsay situated ConEd & Verizon services for one client and moved on to coordinating a full-member move, which this client did NOT want to be involved in the dirty details. Lindsay coordinated with the moving company—separate from the cost of Onward’s services—to make sure they were only moving her stuff, nothing that was contested. With every move, there’s a comprehensive list the movers are supposed to follow created by Lindsay and the client. Generally, once the truck’s loaded, the movers transport the items to the new location, assemble any furniture and field any decor deliveries. The whole point is for all clients to come home to their new life, which requires A LOT of planning from the furniture, to the decor, to the utilities, to the food in the fridge. She manages from afar and keeps tabs with point people each step of the way. Then, she worked on a road-map using Trello for a new client looking at location preferences, financial means, functional services (water, gas, electric, cable, WiFi, etc.) & more. She also took two quick calls, first from Onward’s SEO freelancer to determine what would be the best course of action for the site. Lindsay learned the site needed to incorporate keywords, improve the copy on the site, and create more content keeping in mind trending topics on the internet for higher website traffic. She said there comes a time in a small business owner’s life when she or he has to make the decision to outsource or not, and she’s grateful that she’s in the position to be able to.
“I could learn how to do all this stuff, it would just take a lot of time”
The other call was from her fiancé, Ryan, who was preparing for a video shoot the day after this for the non-profit he founded, Corporate Responsibility Rankings. CRR aims to make it easier to buy responsibly with labels of transparency on products. These labels tell you how the company stacks up in terms of fair and equitable employment practices, environmental impact, and charitable efforts. “When Ryan is not saving the world, he’s helping plan our wedding next year,” Lindsay said. On this day, they talked about selecting a florist.
“It’s nice to be with someone who knows that it’s like to create something from nothing.”
When asked about their relationship dynamic as separate entrepreneurs, Lindsay said it’s great to be with someone that understands the desire to create something and also has the desire to help people. While Lindsay’s more of a “throw spaghetti at the wall and see what sticks” type of person, Ryan’s more methodical. She believes the ideal entrepreneur is a mix of both, but luckily they get enough doses of the two perspectives from each other. “No one was more supportive than Ryan,” Lindsay said recounting when she quit her full-time job to start Onward, “what a dream champion.”
Lindsay was on the train from New Brunswick, NJ back to NYC and one of those people talking on the phone. (Not the quiet car this time!) She was chatting with Facebook’s Small Business advertising arm delving advice she wanted to share at a user conference that has since past. On this call, she shared all the ways Instagram and Facebook have been crucial to launching her small business, especially having the ability to target her ideal audience, millennials.
For Onward’s Instagram, Lindsay said she repurposes content from their blog and member newsletter to feature on social media. The goal is to have the social media accounts work as an awareness tool, being on the pulse of breakup news—not breakup gossip—and incorporating themes of reinvention and self-love. She’s found a lot of vendors and members through Instagram.
Lindsay arrived at The Wing‘s Flatiron location, which has been her home base for Onward since she started. The Wing offers all-female co-working spaces with locations all across the country and acts the perfect pit-stop for the early-stage entrepreneur on the go, from programming to food to fast internet.
Once upstairs, she pulled up a sofa seat next to her friend Rachel Charlesworth, who is a fellow Wing member and a branding expert also based out of the Wing spaces. She is launching a company and gave Linsday an update on how progress was going.
Lindsay got back to my emails and prepped a piece on divorce transitions. For the blog, what Onward tries to do is, every Tuesday, offer every Tuesday a different lens of breakups. Since Onward isn’t presenting themselves as experts in the field, they rely on their vendors and other subject-matter experts to spotlight their expertise that relates to breakups on the Onward blog. Sometimes, Onward team members will share their own breakup experiences.
Lindsay also G-chatted a bit with one of her best friends, Stephanie about weekend plans. Being an entrepreneur can be pretty lonely work at times, and she’s grateful to have so many literal co-workers, both at the Wing and remotely through G-chat/text/etc.
On this night, she was speaking on a panel with two other early-stage entrepreneurs in the health/wellness space at an OmniWomen event in midtown.
“It’s always interesting to meet and hear from other entrepreneurs to learn what problem they are trying to solve.”
The two other women on the panel spoke about launching a fitness studio in an underserved community and developing content to teach others to eat and cook better respectively. She talked breakups and how they can be a form of self-care—recognizing that you are in an unhealthy relationship (or one that no longer serves both parties) and choosing to move onward is an incredibly active, positive decision were the themes she hit.
The audience was mostly folks who work in advertising and marketing who were curious to know how the panelists promoted themselves and their companies as they’ve started out until now. She had a great conversation with the moderator from OmniWomen, an affinity organization to groom and retain female talent. It was neat to hear, Lindsay said, about a large company like OmniGroup with over 74,000 employees globally offering such cool professional development opportunities to their employees.
Lindsay feels these panel appearances are not only great networking opportunities but great ways to practice public speaking and to refine your pitch.
As she was exiting the OmniWomen panel, Lindsay discovered she was too late to make it to her rap class downtown. Once a month, she attends Rap Recess which is an extension to the Freestyle Love Supreme Academy, a workshop in freestyle rapping she completed in the summer of 2019. Lindsay loves rap and hip-hop and has been at it for a few years now.
Lindsay said, “it’s a lot of fun to practice spitting and creating rhymes. I’m a pretty terrible beatboxer but it delights me to work other parts of my brain.”
“I’ve never wanted to paint myself in one box.”
When starting your own company, it’s easy for it to encompass every component of you. Lindsay finds inspiration and joy from doing other things outside of Onward. There’s something about tapping into a previous version of yourself that revitalizes your spirit and breaks you out of your current perspective.
Her previous work experience in theater and event production makes her miss the creativity of that world, “there is nothing like it.” Even though she’s not professionally involved in a creative field anymore, attending classes like Rap Recess and others keeps her connected in a way that’s inspiring and fulfilling.
Unfortunately, time wasn’t on her side so she slunk home on the subway.
Lindsay got home between 9:00pm-9:30 pm on this day.
She likes to cook, but this night’s dinner was falafel from Seamless with Ryan. They chilled together and pressed play on the final season of Friday Night Lights (her third watch, by the way). She also tries to read a little to wind down. She’s presently reading the Golden State Killer book, which was too scary for her for pre-bed reading on this night.
Lindsay passionately worked in Broadway and live-event production for almost a decade, a job in the intersection of production, logistics and creativity. While she was working full-time, she was also working for Hillary Clinton’s 2016 presidential campaign for the Advance Events team. Right before the 2016 election, she experienced a breakup from a serious, five-year relationship. The election results and the heartbreak combined brought Lindsay to a light-bulb moment. Lindsay’s production skills made her realize, “as horrible as this was, I kind of had the skills and resources that a lot of people in this situation wouldn’t have.” Her best friend, now Co-Founder, was also experiencing a breakup and after analyzing the two situations, she realized, “there’s something here.”
“There is a similar skillset that production requires in getting people out of a breakup.”
And the breakup concierge business model was born. Onward launched in February of 2019, but it took a while for the idea to bloom into a full-fledged personal and professional investment. Lindsay and her co-founder had been workshopping the idea around and validating feedback followed. But it wasn’t until tragedy struck again in her life with the passing of her father that she thought to herself, “life is too friggin’ short.”
“If I don’t do this now, when I have the energy and motivation, I am missing my window.”
She quit her full-time job she loved, applied for grants, joined a female-focused co-working space and Lindsay, as she put it, “jumped in and just did it.”
What is your advice those who aspire to be like you?
If you’re looking to start your own business, Lindsay advises starting where you can. Given how expensive starting a business can be and how isolating and lonely entrepreneurship is most of the time, start small and take the time to figure out if your passion is a side hustle or something more.
“Business takes a lot of time and a lot of risks, so if there’s a smaller version of the idea you started with, build it from there.”
If you do your job to the best of your ability, what value do you bring to the world?
Lindsay’s the kind of person that wants to be as helpful, practical and resourceful as possible. But given her experience, she’s realized, “the very best solution may involve more time and more money than you have or can offer.” However, knowing that doesn’t mean the next best thing can’t yield the outcome imagined. Linsday said her value is in helping her clients arrive at the decision they need to make and letting them know everything will be okay. Her best work is when she’s giving her clients the tools and resources they need to carry out courage and cultivate resilience.
Which job do you want to experience next?
Jobs like Lindsay‘s
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