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Want A Career Change? Do These Five Things First

Avoid a few mistakes with a foolproof plan of action.

Workin' Girl

We all know that the pandemic has been an eye-opener for professionals forced to work from home, isolate, and now, deal with the back-to-office mania. In fact, research by insurance giant Prudential has found that 1 in 4 workers are looking toward new career horizons, and another recent survey of professionals ages 18-24 found that 66% have felt stuck in their careers since the pandemic began.


With realizations that come from new challenges, there's renewal, and with renewal there's the opportunity to get into new boss moves. And, per usual, we've got our xoNecole tribe covered with the tea on how to change your career and walk into the abundance you deserve.

1. Get real about what you really hate: the job or the career path itself.

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Before you send that resignation email, stop selling that product, or move out of town to start over, it's always a good idea to take account of your why. Write down the pros and cons of your current career and evaluate whether you're just tired of your current situation or whether you need to throw the whole career away.

Use a simple two-column method (with a space for pros on one side and cons on the other) and be totally honest with yourself. Then, evaluate whether the things you like and dislike about the work you do apply to just the job or the profession as a whole.

For example, my first job out of college was working as a copy editor at a small newspaper owned by a large publisher. I surely didn't get a journalism degree to be a copy editor. I wanted bylines and notoriety, and copy editors typically sat in an office all day, staring at copy, making corrections, and designing news pages. I took the gig because I had a mentor who advised me to try it, and many of my classmates—who only applied for the writing and newscaster openings—found themselves unemployed for longer than I could stomach. I eventually found that I hated being far away from my family and I felt like the slow, conservative culture in the small town where the newsroom was located was a horrible fit for me.

On the flip side, I loved my coworkers, enjoyed being challenged, and was offered a blog for the newspaper's website, which helped diversify my duties and scratch my writing itch. When I was ready to leave, I strategized for the opportunity for upward mobility (i.e. working at said large publisher's headquarters). I stuck it out, advanced, and after two years, ended up getting hired at the headquarters... in New York. I found that I loved all aspects of journalism and that it wasn't the nature of the job, but the environment. I also got to be in the epicenter of my industry, eventually moved on to magazine writing and editing, and the rest is history.

2. Dip your toe in new waters before taking the leap.

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I know, I know. If you're already juggling a demanding day job, how can you find the time to take on more? Well, sis, think outside the box on this one. Your current job might have opportunities to collaborate or lead projects with other departments, allowing you to really flex other passions and skills that have all but died in your current role.

Have coffee dates or virtual chats with coworkers who work in departments that are doing things you might be interested in or might allow you to tap into other aspirations. This is a great way to test out a new "career" without actually leaving your company or totally reinventing the wheel.

I'm one of those "geriatric millennials" who has always been fascinated by the Internet and what can be done online. (My brother's a computer geek and engineer, so I grew up intrigued and wowed by the things he could do or create.) I started working in digital media when the whole concept was super-new and "risky" for publishing houses. Print was king back then (early 2000s sis. Don't try me!). I'd volunteer, as a print editor, to take on website editing and writing that nobody else had the time (or desire) to bother with. Doing so allowed me to become somewhat of a tech geek, expand my knowledge of SEO, ad sales, traffic, video production, and website design.

I also got to work with IT professionals and tech disruptors who were already ahead of the game in that arena. In addition, I got promoted a tad quicker than my peers, becoming a manager before 30. While it didn't lead to a total career change to become a bonafide app builder or full-time blogger (which I actually regret because I missed the money boat on that one), it did enhance my experience at work and kept those nasty feelings of stagnation at bay.

Other great ways to test the waters of a new career: Volunteer for a role at an organization, take some courses on subjects related to your dream career, add just one or two new services of products to your offerings to see how they do with clients or customers, or start a part-time side hustle doing whatever that future dream gig entails.

3. Take an assessment.

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Don't shake your head, yet. This might seem like something super-boring, technical, and annoying, but there are so many assessments that can be super-helpful in your journey to figure out your next career move. They're a great way to find out more about your skills, your passions, and how best to use them. I was initially skeptical of these until I was forced to do more than a few for my master's program coursework. The insights were amazingly enlightening and helped me clarify what I wanted to do with the next five years of my work life.

Some are free (like this one and this one) and some are an investment (like this one. Trust me sis, it's worth it.) You can find out personality traits that match with certain vocations, pinpoint your leadership strengths and weaknesses, and get recommendations on various types of jobs or roles that are a great fit—or might not be.

They're especially helpful when you're at a place of transition and are not quite sure which way to go (which is where I was a few years ago. I hit a peak in my career that led to major feelings of fear, inadequacy, and utter confusion).

When you're armed with information and resources to at least point you in the right direction to find the answers you need about your next career phase, it's easier to navigate the bumps that come with that journey. (Check out another great list of assessments here.)

4. Get a coach.

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Investing in a transitions, career, or life coach is something that can bring priceless returns. Just like you'd get a realtor to help find your dream home and navigate the sometimes lengthy and complicated process of searching and closing, it's a good idea to get a coach for a major decision like a career change. You might say, "Well why pay them? What do I get for my money." Uhhhhh, peace of mind, clarity, organization, and direction.

I'd been working in media for over a decade and never thought I needed a coach until I decided to up and quit my job in management to work for myself. I'd always had decent-paying, health-benefits-offering positions at prestigious companies, and when I got my first big client within 2 weeks of going solo, I thought I'd made it. Wrong. I eventually lost that client, had nothing to fall back on, and had to really come to terms with the fact that I had big-talk entrepreneurial aspirations with a spoiled, scared, check-to-check, nine-to-fiver mindset.

I broke down and finally connected with a mastermind coach who was not only a successful entrepreneur herself, but someone who could relate to the shame and trauma I felt after not being an instant and consistent success in self-employment.

She helped me map out a better plan of action for my freelance projects, sift through my jumbled ideas and turn them into feasible concepts that were sellable and scalable, update my time management approach, and she provided a sounding board for times of frustration and utter failure.

If you can't afford to hire a coach, check out free resources from organizations like the National Urban League, via your local library (which sometimes lists opportunities to connect with local coaches), and through scholarship, grant, and nonprofit initiatives. And don't forget to look in your own backyard: Many sorority, alumni or civic organizations offer free coaching services, and there are Facebook and LinkedIn groups dedicated to it.

5. Check your lifestyle and finances.

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Baby, rent is always due, and don't let IG fool you. I really don't have to tell you this but I will: Making a career change can be scary, super-risky, and utterly stressful. At one point, I thought I could be a full-time social media manager. I'd been in media for a while and had dabbled in various aspects of the industry, so I thought, "Hey, why not? How different can it be?"

Chile, talk about a hot mess. I hated the monotonous and tedious scheduling, I was not that great nor competitive at creating awesome videos and graphics, and I began to feel that feedback was more like annoying nitpicking (which it really wasn't. I mean, they were paying and deserved to get what they wanted). Also, I didn't like being on-call due to the nature of managing social, and I'm really not into the constant pressure of increasing audiences through that medium. It just wasn't something I enjoyed doing at all

The change was a big mistake that cost me lots of money and time that I really couldn't afford to lose at the time. I'd stopped taking on clients for other services to switch fully into social media management, so, again, I had no alternate income to fall back on. I parted ways with several clients at that time because, let's face it: I hated being a social media manager and really won't give my best to a role I hate. That put a strain on my pockets and led to burnout that negatively impacted my true passions: content management, editing, and writing.

Ask yourself the hard questions: Can I afford to make a change right now? If it's not a good fit or happens to be a mistake, will my savings cover me for a while? If my new career shift includes taking a pay cut, investing more money in overhead costs, or losing a current audience or client, am I OK with that? Does my dream future lifestyle fit with what that industry normally pays people, and if not, again, am I OK with that? Will I be able to leverage opportunities in order to be financially free? Will the shift actually lead to more financial gains or more debt and little return on investment?

And I'm from the school of You Really Can Do Anything You Put Your Mind To, so I'm not going to get into the narrative of avoiding taking action due to money issues. (I mean, I get it: Some folks are scared to make a change if the circumstances for doing so aren't perfect. Well, not me.) Let's reverse that: As my mother would say, find a way and get it done. If you have to adjust your budget, take on more hours to earn funds to put in your "I Quit" account, lean on friends and family (word to Granny and Ma!), work with an adviser to map out the financial part of your transition, or take a leap of faith, do it.

Changing your career or totally shifting professional focus can be a roller coaster drama with crazy characters, several acts, random mini-failures, and many intermissions, but I liken the process to anything beautiful and fulfilling in one's life: If it's something you're called to do, the not-so-sweet stuff is well worth it.

For more job search tips, career advice and profiles, check out the xoNecole Workin Girl section here.

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You may not know her by Elisabeth Ovesen – writer and host of the love, sex and relationships advice podcast Asking for a Friend. But you definitely know her other alter ego, Karrine Steffans, the New York Times best-selling author who lit up the literary and entertainment world when she released what she called a “tell some” memoir, Confessions of a Video Vixen.

Her 2005 barn-burning book gave an inside look at the seemingly glamorous world of being a video vixen in the ‘90s and early 2000s, and exposed the industry’s culture of abuse, intimidation, and misogyny years before the Me Too Movement hit the mainstream. Her follow-up books, The Vixen Diaries (2007) and The Vixen Manual: How To Find, Seduce And Keep The Man You Want (2009) all topped the New York Times best-seller list. After a long social media break, she's back. xoNecole caught up with Ovesen about the impact of her groundbreaking book, what life is like for her now, and why she was never “before her time”– everyone else was just late to the revolution.

xoNecole: Tell me about your new podcast Asking for a Friend with Elisabeth Ovesen and how that came about.

Elisabeth Ovesen: I have a friend who is over [at Blavity] and he just asked me if I wanted to do something with him. And that's just kinda how it happened. It wasn't like some big master plan. Somebody over there was like, “Hey, we need content. We want to do this podcast. Can you do it?” And I was like, “Sure.” And that's that. That was around the holidays and so we started working on it.

xoNecole: Your life and work seem incredibly different from when you first broke out on the scene. Can you talk a bit about the change in your career and how your life is now?

EO: Not that different. I mean my life is very different, of course, but my work isn't really that different. My life is different, of course, because I'm 43. My career started when I was in my 20s, so we're looking at almost 20 years since the beginning of my career. So, naturally life has changed a lot since then.

I don’t think my career has changed a whole lot – not as far as my writing is concerned, and my stream of consciousness with my writing, and my concerns and the subject matter hasn’t changed much. I've always written about interpersonal relationships, sexual shame, male ego fragility, respectability politics – things like that. I always put myself in the center of that to make those points, which I think were greatly missed when I first started writing. I think that society has changed quite a bit. People are more aware. People tell me a lot that I have always been “before my time.” I was writing about things before other people were talking about that; I was concerned about things before my generation seemed to be concerned about things. I wasn't “before my time.” I think it just seems that way to people who are late to the revolution, you know what I mean?

I retired from publishing in 2015, which was always the plan to do 10 years and retire. I was retired from my pen name and just from the business in general in 2015, I could focus on my business, my education and other things, my family. I came back to writing in 2020 over at Medium. The same friend that got me into the podcast, actually as the vice president of content over at Medium and was like, “Hey, we need some content.” I guess I’m his go-to content creator.

xoNecole: Can you expound on why you went back to your birth name versus your stage name?

EO: No, it was nothing to expound upon. I mean, writers have pen names. That’s like asking Diddy, why did he go by Sean? I didn't go back. I've always used that. Nobody was paying attention. I've never not been myself. Karrine Steffans wrote a certain kind of book for a certain kind of audience. She was invented for the urban audience, particularly. She was never meant to live more than 10 years. I have other pen names as well. I write under several names. So, the other ones are just nobody's business right now. Different pen names write different things. And Elisabeth isn’t my real name either. So you'll never know who I really am and you’ll never know what my real name is, because part of being a writer is, for me at least, keeping some sort of anonymity. Anything I do in entertainment is going to amass quite a bit because who I am as a person in my private life isn't the same a lot of times as who I am publicly.

xoNecole: I want to go back to when you published Confessions of a Video Vixen. We are now in this time where people are reevaluating how the media mistreated women in the spotlight in the 2000s, namely women like Britney Spears. So I’d be interested to hear how you feel about that period of your life and how you were treated by the media?

EO: What I said earlier. I think that much of society has evolved quite a bit. When you look back at that time, it was actually shocking how old-fashioned the thinking still was. How women were still treated and how they're still treated now. I mean, it hasn't changed completely. I think that especially for the audience, I think it was shocking for them to see a woman – a woman of color – not be sexually ashamed.

I hate being like other people. I don't want to do what anyone else is doing. I can't conform. I will not conform. I think in 2005 when Confessions was published, that attitude, especially about sex, was very upsetting. Number one, it was upsetting to the men, especially within urban and hip-hop culture, which is built on misogyny and thrives off of it to this day. And the women who protect these men, I think, you know, addressing a demographic that is rooted in trauma that is rooted in sexual shame, trauma, slavery of all kinds, including slavery of the mind – I think it triggered a lot of people to see a Black woman be free in this way.

I think it said a lot about the people who were upset by it. And then there were some in “crossover media,” a lot of white folks were upset too, not gonna lie. But to see it from Black women – Tyra Banks was really upset [when she interviewed me about Confessions in 2005]. Oprah wasn't mad [when she interviewed me]. As long as Oprah wasn’t mad, I was good. I didn't care what anybody else had to say. Oprah was amazing. So, watching Black women defend men, and Black women who had a platform, defend the sexual blackmailing of men: “If you don't do this with me, you won't get this job”; “If you don't do this in my trailer, you're going to have to leave the set”– these are things that I dealt with.

I just happened to be the kind of woman who, because I was a single mother raising my child all by myself and never got any help at all – which I still don't. Like, I'm 24 in college – not a cheap college either – one of the best colleges in the country, and I'm still taking care of him all by myself as a 21-year-old, 20-year-old, young, single mother with no family and no support – I wasn’t about to say no to something that could help me feed my son for a month or two or three.

xoNecole: We are in this post-Me Too climate where women in Hollywood have come forward to talk about the powerful men who have abused them. In the music industry in particular, it seems nearly impossible for any substantive change or movement to take place within music. It's only now after three decades of allegations that R. Kelly has finally been convicted and other men like Russell Simmons continue to roam free despite the multiple allegations against him. Why do you think it's hard for the music industry to face its reckoning?

EO: That's not the music industry, that's urban music. That’s just Black folks who make music and nobody cares about that. That's the thing; nobody cares...Nobody cares. It's not the music industry. It's just an "urban" thing. And when I say "urban," I say that in quotations. Literally, it’s a Black thing, where nobody gives a shit what Black people do to Black people. And Russell didn't go on unchecked, he just had enough money to keep it quiet. But you know, anytime you're dealing with Black women being disrespected, especially by Black men, nobody gives a shit.

And Black people don't police themselves so it doesn't matter. Why should anybody care? And Black women don't care. They'll buy an R. Kelly album right now. They’ll stream that shit right now. They don’t care. So, nobody cares. Nobody cares. And if you're not going to police yourself, then nobody's ever going to care.

xoNecole: Do you have any regrets about anything you wrote or perhaps something you may have omitted?

EO: Absolutely not. No. There's nothing that I wish I would've gone back and said to myself, no. I don’t think at 20-something years old, I'm supposed to understand every little thing. I don't think the 20-something-year-old woman is supposed to understand the world and know exactly what she's doing. I think that one of my biggest regrets, which isn't my regret, but a regret, is that I didn't have better parents. Because a 20-something only knows what she knows based on what she’s seen and what she’s been taught and what she’s told. I had shitty parents and a horrible family. Just terrible. These people had no business having children. None of them. And a lot of our families are like that. And we may pass down those familial curses.

*This interview has been edited and condensed

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Feature image courtesy of Elisabeth Ovesen

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