

I Have Had Over 20-Something Jobs & This Is How To Job Hop Like A Pro
My first job was working as a floral assistant and cashier at a local flower shop. It was quite rewarding, engaging with consumers as they picked up bouquets and arrangements for various occasions. I kept that job for a year before transitioning into a completely different industry. From then up to today, I’ve had over 20-something jobs. Now, I know what you may be thinking: “How have you been able to have so many jobs and bypass the flood of questions that come with job hopping?”
Much of job hopping appropriately requires a clear strategy and understanding of what you are hoping to achieve. Leaving an organization preemptively because you are underpaid, undervalued, or treated poorly is a justifiable reason to job hop. Leaving an organization because you feel you have capped on growth opportunities, even if it's sooner than expected, is a justifiable reason to job hop.
You shouldn’t, however, job hop if you aren’t clear on the fundamentals of your job function. For example, leaving your well-paying role as Project Manager after four months because a TikTok video made you feel you could make more money elsewhere is not a good idea if you are still new to the responsibilities of a Project Manager.
There is a right and wrong way to job hop. To keep things easy as you navigate your corporate journey, here are the general steps you should follow:
@kyyahabdul Is Job Hopping Bad?? No, not inherently. BUT there is a right and wrong way to do it. If you have no idea what you are doing and just job hop to make more money, it will eventually catch up with you and somoone will without a doubt call you out on it. This could make it harder for you to get jobs in the future. The best practice for job hopping is to leave a role once you have mastered it. #corporatelife #corporatetiktok #corporateamerica #jobhopping #jobhopper #jobhop #howtojobhop
Step 1: Stick to the rule of 6 months for entry-level and 18 months for mid-level roles.
Entry-level jobs (0-2 years of experience) are not as challenging as corporations make them out to be. Depending on the industry, responsibilities for early career roles can be mastered in under one year as they tend to be more supporting roles than project-owning roles. Some people may even master their responsibilities within 3 to 6 months. Whether your reasoning is to make more money or have a higher title, you should start looking for new opportunities around the 6-month mark.
Mid-senior level roles are a little different as you’re more likely to own projects from inception to completion. It’s better to remain in these roles until a project completes which spans, on average, from 12 to 18 months. If you leave too many mid-senior roles after 6 months or so, future employers will question or ability to see a projection through completion. It will be a challenge for them to invest in you when you have not shown your ability to invest in a company project.
After this allotted amount of time, you should start to explore other opportunities for higher pay and/or a higher title. Another reason to remain in mid-senior roles for 12 to 18 months is to ensure at least a fraction of your equity vests if you are awarded any at the time of accepting your job offer.
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Step 2: Leave the job after you have mastered the role.
As mentioned above, it’s important to put a 'skill frame' on your job opportunities as opposed to a 'time frame.' The 6-month and 18-month rule in the first step is in regard to the minimum amount of time you should spend in a role. Many people will remain in a job, that does not serve them, for 5, 10, or even 15 years. They have mastered their role and won’t leave because they don’t think they have spent enough time with their organization.
To be frank, your allotted amount of time means nothing if you’re not growing. The reason a professional with 4 years of experience gets the role over the professional with 10 years of experience is that the person with 4 years (the job hopper) had robust experience. They left jobs that stunted their growth and matriculated into roles that diversified their skill set. Meanwhile, the person with 10 years of experience can only serve future employers in limited capacity. They lack a diverse skill set due to their stagnancy.
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Step 3: Address your “job hopping” when transitioning to new roles.
When you are interviewing for a new role, and they ask you why you left company a, b, and c, each after 1 year you explain that: (1) you outgrew your role and felt it was time to transition into a more challenging position or (2) you would have loved to continue growing with your previous organization(s), however, there were no opportunities for growth and no transparency as to when such opportunities may become available.
If you are wanting to job hop but fear what companies may say, don’t. I promise you, a good company will care less about the amount of time you spent and more about what you can bring to the table. Good companies will understand that leaving a toxic work environment or a place that stunts you professionally is a viable reason to job hop. Don’t let a company, recruiter, or colleague guilt you into staying in a role or at a company you’re not pleased with.
A recruiter once told me, “You’re going to ruin your career. You can’t just go hopping from job to job thinking companies will still hire you.” August 2022 marked my 9th year working within the pharmaceutical industry. I am gainfully employed, and content with my current employer. I turned out okay and you will too.
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Amber Riley has the type of laugh that sticks with you long after the raspy, rhythmic sounds have ceased. It punctuates her sentences sometimes, whether she’s giving a chuckle to denote the serious nature of something she just said or throwing her head back in rip-roarious laughter after a joke. She laughs as if she understands the fragility of each minute. She chooses laughter often with the understanding that future joy is not guaranteed.
Credit: Ally Green
The sound of her laughter is rivaled only by her singing voice, an emblem of the past and the future resilience of Black women stretched over a few octaves. On Fox’s Glee, her character Mercedes Jones was portrayed, perhaps unfairly, as the vocal duel to Rachel Berry (Lea Michele), offering rough, full-throated belts behind her co-star’s smooth, pristine vocals. Riley’s always been more than the singer who could deliver a finishing note, though.
Portraying Effie White, she displayed the dynamic emotions of a song such as “And I'm Telling You I'm Not Going” in Dreamgirls on London’s West End without buckling under the historic weight of her predecessors. With her instrument, John Mayer’s “Gravity” became a religious experience, a belted hymnal full of growls and churchy riffs. In her voice, Nicole Scherzinger once said she heard “the power of God.”
Credit: Ally Green
Riley’s voice has been a staple throughout pop culture for nearly 15 years now. Her tone has become so distinguishable that most viewers of Fox’s The Masked Singer recognized the multihyphenate even before it was revealed that she was Harp, the competition-winning, gold-masked figure with an actual harp strapped to her back.
Still, it wasn’t until recently that Riley began to feel like she’d found her voice. This sounds unbelievable. But she’s not referring to the one she uses on stage. She’s referencing the voice that speaks to who she is at her core. “Therapy kind of gave me the training to speak my mind,” the 37-year-old says. “It’s not something we’re taught, especially as Black women. I got so comfortable in [doing so], and I really want other people, especially Black women, to get more comfortable in that space.”
“Therapy kind of gave me the training to speak my mind. It’s not something we’re taught, especially as Black women."
If you ask Riley’s manager, Myisha Brooks, she’ll tell you the foundation of who the multihyphenate is hasn’t changed much since she was a kid growing up in Compton. “She is who she is from when I met her back when she was singing in the front of the church to back when she landed major roles in film and TV,” Brooks says. Time has allowed Riley to grow more comfortable, giving fans a more intimate glimpse into her life, including her mental health journey and the ins and outs of show business.
The actress/singer has been in therapy since 2019, although she suffered from depression and anxiety way before that. In a recent interview with Jason Lee, she recalls having suicidal ideation as a kid. By the time she started seeing a psychologist and taking antidepressants in her thirties, her body had become jittery, a physical reminder of the trauma stacked high inside her. “I was shaking in [my therapist’s] office,” she tells xoNecole. “My fight or flight was on such a high level. I was constantly in survival mode. My heart was beating fast all the time. All I did was sweat.”
There wasn’t just childhood trauma to account for. After auditioning for American Idol and being turned away by producers, Riley began working for Ikea and nearly missed her Glee audition because her car broke down on the highway while en route. Thankfully, Riley had been cast to play Mercedes Jones. American Idol had temporarily convinced her she wasn’t cut out for the entertainment industry, but this was validation that she was right where she belonged. Glee launched in 2009 with the promise of becoming Riley’s big break.
In some ways, it was. The show introduced Riley to millions of fans and catapulted her into major Hollywood circles. But in other ways, it became a reminder of the types of roles Black women, especially those who are plus-sized, are relegated to. Behind the scenes, Riley says she fought for her character "to have a voice" but eventually realized her efforts were useless. "It finally got to a point where I was like, this is not my moment. I'm not who they're choosing, and this is just going to have to be a job for me for now," she says. "And, that's okay because it pays my bills, I still get to be on television, I'm doing more than any other Black plus-sized women that I'm seeing right now on screen."
The actress can recognize now that she was navigating issues associated with trauma and low self-esteem at the time. She now knows that she's long had anxiety and depression and can recognize the ways in which she was triggered by how the cult-like following of the show conflicted with her individual, isolated experiences behind the scenes. But she was in her early '20s back then. She didn't yet have the language or the tools to process how she was feeling.
Riley says she eventually sought out medical intervention. "When you're in Hollywood, and you go to a doctor, they give you pills," she says, sharing a part of her story that she'd never revealed publicly before now. "[I was] on medication and developing a habit of medicating to numb, not understanding I was developing an addiction to something that's not fixing my problem. If anything, it's making it worse."
“[I was] on medication and developing a habit of medicating to numb, not understanding I was developing an addiction to something that’s not fixing my problem. If anything it’s making it worse.”
Credit: Ally Green
At one point, while in her dressing room on set, she rested her arm on a curling iron without realizing it. It wasn't until her makeup artist alerted her that she even realized her skin was burning. Once she noticed, she says she was "so zonked out on pills" that she barely reacted. Speaking today, she holds up her arm and motions towards a scar that remains from the incident. She sought help for her reliance on the pills, but it would still be years before she finally attended therapy.
This stress was only compounded by the trauma of growing up in poverty and the realities of being a "contract worker." "Imagine going from literally one week having to borrow a car to get to set to the next week being on a private jet to New York City," she says. After Glee ended, so did the rides on private planes. The fury of opportunities she expected to follow her appearance on the show failed to materialize. She wasn't even 30 yet, and she was already forced to consider if she'd hit her career peak.
. . .
We’re only four minutes into our Zoom call before Riley delivers her new adage to me. “My new mantra is ‘humility does not serve me.’ Humility does not serve Black women. The world works so hard to humble us anyway,” she says.
On this Thursday afternoon in April, the LA-based entertainer is seated inside her closet/dressing room wearing a cerulean blue tank top with matching shorts and eating hot wings. This current phase of healing hinges on balance. It’s about having discipline and consistency, but not at the risk of inflexibility. She was planning to head to the gym, for instance, but she’s still tired from the “exhausting” day before. Instead, she’s spent her day receiving a massage, eating some chicken wings, and planning to spend quality time with friends. “I’m not going to beat myself up for it. I’m not going to talk down to myself. I’m going to eat my chicken wings, and then tomorrow I’m [back] in the gym,” she says.
“My new mantra is ‘humility does not serve me.’ Humility does not serve Black women. The world works so hard to humble us anyway."
This is the balance with which she's been approaching much of her life these days. It's why she's worried less about whether or not people see her as someone who is humble. She'd rather be respected. "I think you should be a person that's easy to work with, but in the moments where I have to ruffle feathers and make waves, I'm not shying away from that anymore. You can do it in love, you don't have to be nasty about it, but I had to finally be comfortable with the fact that setting boundaries around my life – in whatever aspect, whether that's personal or business – people are not going to like it. Some people are not going to have nice things to say about you, and you gotta be okay with it," she says.
When Amber talks about the constant humbling of Black women in Hollywood, I think of the entertainers before her who have suffered from this. The brilliant, consistent, overqualified Black women who have spoken of having to fight for opportunities and fair pay. Aretha Franklin. Viola Davis. Tracee Ellis Ross. There's a long list of stars whose success hasn't mirrored their experiences behind the scenes.
Credit: Ally Green
If Black women outside of Hollywood are struggling to decrease the pay gap, so, too, are their wealthier, more famous peers.
Riley says there’s been progress in recent years, but only in small ways and for a limited group of people. “This business is exhausting. The goalpost is constantly moving, and sometimes it’s unfair,” she says. But, I have to say it’s the love that keeps you going.”
“There’s no way you can continue to be in this business and not love it, especially being a plus-sized Black woman,” she continues. “We’re still niche. We’re still not main characters.”
"There’s no way you can continue to be in this business and not love it, especially being a plus-sized Black woman. We’re still niche. We’re still not main characters.”
Last year, Riley starred alongside Raven Goodwin in the Lifetime thriller Single Black Female (a modern, diversified take on 1992’s Single White Female). It was more than a leading role for the actress, it also served as proof that someone who looks like her can front a successful project without it hinging on her identity. It showcased that the characters she portrays don’t “have to be about being a big girl. It can just be a regular story.”
Riley sees her work in music as an extension of her efforts to push past the rigid stereotypes in entertainment. Take her appearance on The Masked Singer, for instance. Riley said she decided to perform Mayer’s “Gravity” after being told she couldn’t sing it years earlier. “I wanted to do ‘Gravity’ on Glee. [I] was told no, because that’s not a song that Mercedes would do,” she says. “That was a full circle moment for me, doing that on that show and to hear what it is they had to say.”
As Scherzinger praised the “anointed” performance, a masked Riley began to cry, her chest heaving as she stood on stage, her eyes shielded from view. “You have to understand, I have really big names – casting directors, producers, show creators – that constantly tell me ‘I’m such a big fan. Your talent is unmatched.’ Hire me, then,” she says, reflecting on the moment.
Recently, she’s been in the studio working on original music, the follow-up to her independently-released debut EP, 2020’s Riley. The sequel to songs such as the anthemic “Big Girl Energy” and the reflective ballad “A Moment” on Riley, this new project hones in on the singer’s R&B roots with sensual grooves such as the tentatively titled “All Night.” “You said I wasn’t shit, turns out that I’m the shit. Then you called me a bitch, turns out that I’m that bitch. You said no one would want me, well you should call your homies,” she sings on the tentatively titled “Lately,” a cut about reflecting on a past relationship. From the forthcoming project, xoNecole received five potential tracks. Fans likely already know the strengths and contours of Riley’s vocals, but these new songs are her strongest, most confident offerings as an artist.
“I am so much more comfortable as a writer, and I know who I am as an artist now. I’m evolving as a human being, in general, so I’m way more vulnerable in my music. I’m way more willing to talk about whatever is on my mind. I don’t stop myself from saying what it is I want to say,” she says.
Credit: Ally Green
“Every era and alliteration of Amber, the baseline is ‘Big Girl Energy.’ That’s the name of her company,” her manager Brooks says, referencing the imprint through which Riley releases her music after getting out of a label deal several years ago. “It’s just what she stands for. She’s not just talking about size, it’s in all things. Whether it’s putting your big girl pants on and having to face a boardroom full of executives or sell yourself in front of a casting agent. It’s her trying to achieve the things she wants to do in life.”
Riley says she has big dreams beyond releasing this new music, too. She’d love to star in a rom-com with Winston Duke. She hasn't starred in a biopic yet, but she’d revel in the opportunity to portray Rosetta Tharpe on screen. She’s determined that her previous setbacks won’t stop her from dreaming big.
“I think one of my superpowers is resilience because, at the end of the day, I’m going to kick, scream, cry, cuss, be mad and disappointed, but I’m going to get up and risk having to deal with it all again. It’s worth it for the happy moments,” she says.
If Riley seems more comfortable and confident professionally, it’s because of the work she’s been doing in her personal life.
She’d previously spoken to xoNecole about becoming engaged to a man she discovered in a post on the site, but she called things off last year. For Valentine’s Day, she revealed her new boyfriend publicly. “I decided to post him on Valentine’s Day, partially because I was in the dog house. I got in trouble with him,” she says, half-joking before turning serious. “The breakup was never going to stop me from finding love. Or at least trying. I don’t owe anybody a happily ever after. People break up. It happens. When it was good, it was good. When it was bad, it was terrible, hunny. I had to get the fuck up out of there. You find happiness, and you enjoy it and work through it.”
Credit: Ally Green
"I don’t owe anybody a happily ever after. People break up. It happens. When it was good, it was good. When it was bad, it was terrible, hunny. I had to get the fuck up out of there. You find happiness and you enjoy it and work through it.”
With her ex, Riley was pretty outspoken about her relationship, even appearing in content for Netflix with him. This time around is different. She’s not hiding her boyfriend of eight months, but she’s more protective of him, especially because he’s a father and isn’t interested in becoming a public figure.
She’s traveling more, too. It’s a deliberate effort on her part to enjoy her money and reject the trauma she’s developed after experiencing poverty in her childhood. “I live in constant fear of being broke. I don’t think you ever don’t remember that trauma or move past that. Now I travel and I’m like, listen, if it goes, it goes. I’m not saying [to] be reckless, but I deserve to enjoy my hard work.”
After everything she’s been through, she certainly deserves to finally let loose a bit. “I have to have a life to live,” she says. “I’ve got to have a life worth fighting for.”
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Introducing Chief Mom Officer: Where Working Moms Come First
xoNecole's Chief Mom Officer explores the 18-month post-pregnancy journey through the lens of our very own Chief Mom Officer, Shakyna Bolden. The series will serve as an inspirational and resourceful guide to help get through the early days of new motherhood as working moms knowing they are not alone in the hardships.
“I want to build my work around my life, and not my life around my work.”
I typed these words in my iPhone Notes as I fed my newborn daughter one morning during the first few weeks of having her earthside. I didn’t have much time for page-filled journal entries as my days were filled with nonstop feedings, soothing, and recovery…but I knew I needed to give those words space and life.
Prior to my maternity leave, I, like most working moms, was burning fumes juggling work and life. Since 2019, I’ve been running revenue operations here at this really cool company you may have heard of called xoNecole (hehe). I’ve been behind the scenes building our brand partnerships and negotiating deals with companies such as Ulta Beauty, Toyota, Target, Spotify, SheaMoisture, etc.
Courtesy of Shakyna Bolden
I’ve co-produced our signature events like ElevateHER and Pajamas & Lipstick while conceptualizing, selling, building, and distributing our original video and podcast content and podcast. The list goes on and on. I’ve helped build this small but brilliant company into what it is today, all while running my own small family. And that is not an easy feat.
In all truth, trying to be the best mom and partner I can be while also leading in my job has felt at times like a whirlwind where the rest of my life is passing me by. I don’t quite know where or when it happened, but I swear somebody pushed the fast-forward button in life, and I’m losing my edges trying to keep up.
My mind and body get so preoccupied with the management of life that my soul sits on the sidelines, waiting to take the reins and intentionally live it.
So many facets of my life, from my health and well-being to my hobbies and passions, have been placed on the back burner while tending to my young family and growing in my career has taken center stage. And for the longest time, I’ve wanted to flip the switch, but the pace of life just hasn’t let me restack my priorities.
That is, until now.
Courtesy of Shakyna Bolden
When I found out I was pregnant with my daughter last year, I couldn’t imagine adding more to my already full plate. Simultaneously, I was also relieved to know that my upcoming maternity leave would force me to press pause and catch my breath. Her birth in January 2023 was a much-needed reset, to say the least.
My maternity leave was the first time since 2019 that I had a second for dreams that were buried in the back of my heart to bubble up to the surface of my reality. I got a taste of what it was like to solely focus on my well-being and my home life. And I liked it a lot. My healing. My recovery. Sitting and really taking quiet time with God to search the unattended areas in the garden of my life.
I was cooking homemade meals on the regular and actually sitting down with my family at the table to eat. As grueling as those first newborn weeks can be, I was enjoying the long-awaited shift in my priorities; and I wanted that shift to stick. I didn’t want it to fade away after my maternity leave.
I want to build my work around my life and not my life around my work.
As a leader of an organization that speaks to millions of women every day about their well-being (and also in leading a team of majority women), I feel it’s my responsibility to carry this shift forward boldly. This is why I’m launching a new column here at xoNecole: Chief Mom Officer!
As I return to work full-time this month from my maternity leave, I want to regularly share my experience of trying to harmonize work and life. As an audience, you all share your raw, unfiltered journeys with us. For years, they’ve undoubtedly inspired me. I want to show up and do the same because I know this shift in my life will be quite the journey.
So for all my Chief Mom Officers—those of us who are constantly merging the imperfect and chaotic worlds of leadership in the office and wearing our crowns at home—I invite you to come on this journey with me and celebrate the ebbs and flows in how we show up for each.
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Featured image courtesy of Shakyna Bolden