Career transitions are tough, personal, and deeply emotional. Maybe you are looking to pivot but feel stuck; maybe you’ve been out of the workforce for years and feel intimidated watching peers climb the ladder; or maybe you’ve landed in one of the most vulnerable positions of all: fired. In those moments, calling up an executive coach feels like the obvious move. But Weston's Jodi Rabinowitz isn’t interested in the obvious.
“I’m not a coach. I am a wingwoman,” Jodi tells Westport Lifestyle. “Everybody and their mother is a coach. And that’s great. But I have a lifetime of experience, and I do not leave my clients’ sides from the day they hire me to well after they place.”
As the founder of Congratulations, You’re Fired, Jodi is focused on reframing what many view as an irrevocable gut punch into a professional renaissance. Her path to her now-calling of “career wingwoman” was circuitous (but of course). Armed with a master’s degree in social work from the University of Pennsylvania, she cut her teeth in the psychiatric ER at N.Y.C.’s Bellevue Hospital. That experience taught her crisis management skills, coupled with what it really means to exhibit empathy. She took those lessons into her next life, in corporate America, debriefing executives after national crises, training leaders, climbing the ladder at financial firms, and leading talent development at Zoom as it skyrocketed through the pandemic.
Along the way, she was fired five times.
“I have the best career story,” she says. “Every single time I’ve been fired, I rose higher and higher.”
While standard career services obsess over optimizing resume keywords for an algorithm, Jodi zeroes in on the human behind the cover letter. “I can do a resume rewrite or a LinkedIn profile like nobody else,” she says. “But the power of what I do is work with the whole person and that relationship. Every person comes with a story and a history.”
Acting as an unflinching sounding board, she helps job seekers unpack their past missteps and align with what genuinely matters in their next chapter. “I am very much a mirror, an accountability buddy, helping people understand the choices they're making consciously,” she explains. When it comes to explaining career gaps or terminations, she works with clients to own their narrative on their own terms: “I help the client find the truth they are comfortable telling, embrace it, and recite it like it’s a chocolate chip cookie recipe.”
Here, Jodi shares her top five strategies for navigating career transitions with honesty, openness, and confidence,
1. Own Your Narrative
Getting terminated is an emotional shockwave. “You absolutely have to honor and make space for what I call a ‘sniper attack,’” Jodi explains. “Even if you see it going on around you, you don't think it’s going to affect you. You have to make space for the anger, the feeling of deceit, the ‘what did I do wrong?’ Honor that space, get it out of your system, and then we get focused.”
Once you’re ready to re-enter the market, drop the shame. Whether you choose full transparency about a misstep or frame a gap around caretaking, find the narrative you can stand behind without flinching. “There’s a range of ways we can tell the truth,” she says. “The kind of employer I’d want to work with would be proud of my courage, appreciate my transparency, and champion my journey.”
2. Relationships Are Everything
Endlessly tweaking keywords to beat automated software is a losing battle. “Sending your resume in with the perfect keywords still only has a 7 percent chance of getting an interview,” Jodi notes. “You get your job through relationships. Period. Full stop. Relationship trumps everything; likability trumps competence.”
Instead of rewriting your credentials for every single job posting, keep your resume at an aggregate “90 percent fit” for your target role and put your energy into people. “Networking happens everywhere—in the grocery line, from your friends, at a dinner party,” she says. “The number one thing about networking is you are not asking for a job. You are looking to build a relationship, to be curious, to learn something.”
Jodi empowers people to network in whatever way feels authentic to them. Did an acquaintance post an insightful article on a topic you’ve been dying to explore? Drop them a note explaining why it resonated. “You're looking to build a relationship. You don't know where that relationship is going to lead. Maybe it'll lead to a job, maybe it'll lead to something you never even knew to expect,” says Jodi. “Your ask is about that connection. It shouldn't be, ‘Can you help me find a job?’”
3. Follow Your Gut
When a new role goes south, it's rarely due to a sudden drop in competence. Most of the time, the warning lights were flashing from the start. “When I talk to clients who come to me with what they consider a failure, we look back at the interview process, and they say, ‘I knew during the interview I shouldn’t have taken it. There was a red flag, and I ignored it,’” Jodi says.
Don't let a lucrative offer make you abandon your non-negotiables. “My job is to help clients root their search in their values and stay true to them,” she explains. “If you want autonomy and creativity, but this sexy job comes up with double the salary and a micromanager, let’s talk about the price. If you swap out values, let’s talk about the consequences.”
4. Everything Is Negotiable
Even in a tight job market, candidates often feel so grateful just to receive an offer that they forfeit their leverage before the ink is dry. “It doesn't mean that they're worth less,” Jodi emphasizes. “I remind people what they are worth and get as much as they possibly can.”
When recruiters press for your salary expectations, flip the script to uncover their actual boundaries. “Instead of getting pinned down, say: ‘I see the range. Can you tell me the difference between someone who gets paid at the bottom of the range versus the top of the range?’” she advises. “Now you’re getting intel, and you know where you calibrate. And remember, compensation is more than base salary—it’s equity, title progression, tuition reimbursement, or unlimited vacation. Companies expect a counter; arm yourself with information and ask.”
5. Why the Holidays Are Prime Time to Power Up
The widespread assumption that corporate hiring goes dark between Thanksgiving and New Year's Day is one of the costliest misconceptions in the job market. While the stress of being unemployed during the holiday season can easily trigger anxiety, Jodi urges candidates to flip their perspective.
“This is a time to give back, meaning give people the opportunity to help you. The more you share your experience, the more opportunities there are for people to help you—and during the holidays, people are feeling particularly generous and giving,” she explains.
That goodwill creates an under-the-radar advantage for anyone willing to stay engaged while competitors check out. “Most candidates think that nobody is around for the holidays, so they power down,” Jodi explains. “But that's an opportunity for people to actually power up. There is more time for hiring managers to sift through their inboxes. Things get slower internally in companies, and managers have more time. Also, at the end of the year, there's a lot of planning for Q1, so sowing seeds for jobs that will open in Q1 is good timing.”
Layer that corporate lull onto a packed social calendar, and suddenly reconnecting feels effortless. “Holiday parties, family gatherings, meeting people for drinks gives you a great excuse to say, ‘Happy New Year, let’s reconnect,’” Jodi says. “Think of it more as an opportunity than a dread, because things definitely happen during quiet times.”
To learn more about Congratulations, You’re Fired, visit congratulationsyourefired.com
“I can do a resume rewrite or a LinkedIn profile like nobody else,” she says. “But the power of what I do is work with the whole person. Everyone comes with a story.”