11 Boss Women On The Biggest Career Mistakes They Made In Their 20s

From choosing love over our career goals to not negotiating, there are so many career mistakes that young women make.

Workin' Girl

From choosing love over our career goals to not negotiating, there are so many career mistakes that young women make.

When we are in our 20s, we are at a very vulnerable state in our lives. For some of us, we just finished college, are working at our first “real" jobs, and we are even starting families. Through the midst of it all, we tend to make simple mistakes as it relates to our careers. Since I graduated from undergrad, I've made plenty of the same mistakes that my female friends have made. I cringe now when I think of them from time to time, but now that I know better, I try my best to do better.

Recently, I was able to connect with a few girl bosses in various careers and personal backgrounds. Each woman shared their biggest career mistake and what they learned from it. Whether you are a graduating college senior, just starting out on your own, or a 20-something woman that is already working, you will be able to benefit from the wisdom of each of the boss women below. Each woman shared her own career mistake and how they've managed to get in formation (slay girl, slay!)

1. Sheena Allen (@whoisSheena)

Entrepreneur & Founder of Sheena Allen Apps & Insta Funds

Learn when to ask for help.

"My biggest career mistake in my 20s was thinking that I could do it all on my own. I started my first tech company as a solo founder and actually waited a good amount of time before seeking mentorship or a team to help in growing my company. I learned that it is important to have a great team in order to build a great company. Trying to do everything on your own will tire and stress you out, which only leads to hurting your company."

2. Troy Washington (@thetroyla)

On-Air News Reporter for KSLA

Have faith in yourself over everyone & everything else.

"I vowed that I would keep this mistake between myself and the reporter who found me bawling my eyes out in the restroom but if it helps someone else out in their career then I suppose the embarrassment is worth it. It took a nightmare live shot during the evening news to teach me that you shouldn't depend on technology. No matter how confident you are in your smartphone, keep a backup plan!

"I was reporting live on a complicated story, the anchor tossed my phone to me and my iPhone cancelled out of my notes. I spent the entire shot stumbling and trying to open the note in my phone. Finally to no avail I tossed the phone back to the anchors feeling defeated. To top it off a viewer came up to me right after and said "got a little tongue tied there at 5." I was mortified. Now no matter how simple or complex the story is I don't complicate things or depend on anything else. I rely on old fashioned pen, pad, bullet points, and what I know. This taught me to trust myself instead of a flimsy note in my phone.

"Believe it or not that moment built my confidence because I knew I could never repeat that mistake. In essence falling on my face has always delivered the best lessons. That was one of my first live shots and I've done hundreds more since then but I'll never forget that one. That's the one that humbled me, it hurt, and taught me that I never wanted to experience it again. In TV, you'll make mistakes and that's inevitable because you're human and likely those mistakes will be broadcasted, but as long as you don't repeat those mistakes, you'll be fine."

3. Shay Lawson (@ShayMLawson )

Diversity Professional & Attorney

Stay hopeful, be fearless, & focus on you.

"I have quite a few career mistakes that comes to mind, but this one sticks out the most:

"When you start working, you need to negotiate. Women make $0.79 for every $1 a man makes, often because men demand more. I didn't even know this was an option when I was in my twenties and in talking to my girlfriends they all agreed that they wish they had negotiated for a higher salary in their first few jobs. I know that's not something most young women are comfortable doing, but men do it ALL THE TIME!!!

"Do the research, know how much people at the job and experience level make, and also come prepared to explain why you want what you're asking be it for relocation, for cost of living, etc. Once you've been offered a job, don't worry you will lose the offer. You're not being petty over pennies, you're getting what you're worth."

4. Emily Drewry (@emily.drewry)

Assistant Social Media Editor at Forbes

Never let the world drown out your voice.

"My biggest mistake thus far has been holding back my thoughts in the workplace because I lacked confidence. As a 22-year-old in my first role out of school, I would frequently wait to bring ideas to the table until I was 100% sure they were good and would be successful. At a certain point, my boss sat me down and told me that I needed to stop focusing on my age and let the ideas speak for themselves.

"It's harder than it sounds to forget about seniority and structure at the office, but doing so let me shine so much more -- and perform better in my role. I try to remember that every day is a new opportunity to prove my skills, and I can't do that without speaking up."

5. Gia Peppers (@giapeppers)

Freelance Entertainment Journalist & On Air Talent (portfolio includes the NBA, BET, ESSENCE, Hot 97 & more)

Be faithful & fearless to YOURSELF.

"I've learned a lot in the first five years of my 20s. The top thing I want other young women to know is that an internship doesn't guarantee a job & you should be loyal to you. In college, I interned almost every semester to make sure I knew exactly what I wanted to do in radio and/or TV. When I graduated, my resume was stacked with "experience." I just KNEW everyone was going to be knocking at my door (or LinkedIn page) with opportunities. But, after I got all my cookout celebrations out of the way, I still had no offers and had to take a job outside of my field to start paying back loans. I hated it. I would go in the bathroom and cry.

"BUT, the resources I had-- like a laptop and overnight car service-- motivated me to work all hours of the night to ensure I would not be there longer than one year. Every moment you have is meant to prepare you for the next one. Do your best in that moment and learn all you can. And, don't be surprised if no one calls you RIGHT after you graduate. It takes a job to get a job. Once you get that job, be loyal to YOU. Our parents grew up in a time when you could stay at one company for 20 years and move up to make more money and gain experience within the company. Unfortunately, our generation doesn't have that security. In many fields, companies barely pay full salaries with benefits. In fact, many of these same companies don't offer raises until an employee threatens to leave. Have your own brand. Make yourself irreplaceable and save for rainy days. In this economic climate, you will probably have some."

6. Nicaila (Caila) Matthews (@CailaKSpeaks)

Senior Manager of Social Marketing at NPR, Founder of CailaKSpeaks.com

Setbacks are temporary. Comebacks create legends.

"My biggest career mistake in my 20s was believing that a job at a big media conglomerate would guarantee happiness and career growth. I was lured by the brand's name and glitzy reputation, but I did not take the time to assess how it aligned with my career goals. Two years and one horrible boss later, I ended up quitting my first job out of college and going through a frustrating period of unemployment, having to move back home, and feeling like a failure. I bounced back by starting to side hustle as a blogger and freelance writer, which led me to my calling as a digital and content marketer.

"If you're reading this and experiencing the same feelings of disappointment and confusion that I did, take the time to assess what you want from your career and life and write down three things you plan to do to get there. I worked at an unrelated job for one and a half years while I hustled to get to the next stage of my career, and ended up living with my parents for three years (two years longer than I planned). In the end I know you'll be happier and that much closer to fulfilling your authentic purpose on this earth. This low point in my career would later propel me into social media marketing and drive me to get my MBA. As I learned from my experience, sometimes you have to take a step backward before you can move forward in pursuit of your goals."

7. Sidnee Michelle Douyon (@sidmich_)

Editorial Operations Assistant at Forbes, and Music and Entertainment Writer/Reporter

Never let your insecurities get in the way.

"My biggest career mistake I've made in my 20's would be second guessing myself. There were times I was hesitant and even shied away from going after certain opportunities and interviews because I thought I didn't have what it takes to execute at 100%. I learned that you have to always go for what you want, especially in your career.

"If you let the fear of failure or your insecurities keep you from going after what you deserve than you'll never reach the heights of your potential. If I could go back in time to prepare myself for the struggles I went through, I wouldn't do anything different but develop a personal confidence within myself early on and really use that as a driving factor to push me forward in my career. Fast forward, I've definitely evolved into a much more confident journalist. Before I even execute an interview or gain an opportunity, I go into it like I know I'm going to "kill this." I also have evolved my work ethic to align with a 'newfound career confidence' where I put in the work & research to be able to go into an assignment or interview 100% confident and prepped."

8. Melissa Kimble (@Melissa_Kimble)

Senior Social Media Manager at EBONY, Leader of The#blkcreatives

Know when to walk away & when to stay.

"The biggest mistake I've made is giving away my power. Anytime my true value wasn't recognized or my energy was being depleted in situations that didn't fulfill or honor me, I should have made the decision to walk away from those things sooner.

"If you're constantly giving away your power, you're living in a place of fear and fear destroys everything, especially your chance to succeed and build the career life you really want for yourself."

9. Ariel Lopez (@ArielLopez__)

Founder of 2020Shift

Try to make the most out of every situation & be the best.

"The biggest mistake I made was making a leap before I was ready (I was 22 at the time) I was working full time at a staffing firm and also on a startup idea when I was presented with an opportunity to work from home. I immediately thought that this is was a dream situation. Make money and have more time to work on my own thing- why not? Unfortunately the position fell through within a month's time and I had to scramble to figure out how to make it. I went through a super rough time and almost had to move back home (nightmare) but was able to land something a few months later. I learned that you can't try to game the system. I wasn't taking the position to give 100% effort to them, I was using them as a catalyst to get my own thing off the ground (bad karma). It also taught me to really think things through before making life altering decisions. I wasn't financially prepared to sustain myself and my expenses if my job didn't work out.

"Ultimately, I took a risk on leaving something stable to pursue the unknown, but I think it paid off. That experience fueled me to do it all over again, just better. I actually don't believe in mistakes, just lessons learned. I recently took the leap again, but this time I had things aligned differently. Since then, I've evolved a ton as entrepreneur and also as a career coach. I'm able to advise people on their careers because of my personal experience. It's also showed me that if I can bounce back once I could do it twice. I'm unafraid because I know what I'm capable of."

10. Emmelie De La Cruz (@EmmelieDeLaCruz)

Author of Make Yourself Marketable & Personal Branding Strategist

Your personal brand is more important than you may think.

"The biggest career mistake I made was believing that I needed the right credentials to be an expert. Have you heard of Malala? Imagine if she censored herself because she considered herself too young and her story insignificant. We wouldn't have the youngest Nobel Peace Prize winner. Our personal brand is a combination of our personality, skill sets, and the value we create for others.

"It is all about who we are, what we do and how others perceive us through those in-person and digital interactions. Building your personal brand inside and outside the workplace is necessary to accelerate your career. Our insecurities around self-promotion, our credentials, and contributions will disappear when we understand that the stakes for us to succeed as a sisterhood are so high that we are almost forced to tell our story for the sake of being a resource to someone else. We have an important story that needs to be told and heard. The unique combination of your personal and professional experience, your skills and accomplishments already make you an expert."

11. Tola Lawal (@tola617)

Entrepreneur & Founder of SixOne7Creative

Never let them see you sweat or lose your cool.

"One of my biggest career mistakes was bringing my emotions to work. In my early 20's I let a co-worker take me out of my professional element and I went OFF in the office. My bosses and co-workers were SHOCKED! I was a great employee and most times I ignored the tomfoolery but at that point I was fed up. As busy as I was supporting a number of senior level executives, I didn't have time. But that day... that day, I had time. But after I lit the office up, I was SO embarrassed. After this mistake, I learned a few things. I learned the importance of a poker face, and that most of what goes on at work is not personal. Don't take any of it personally. If there is an issue, go to your immediate boss, and if that doesn't resolve the issue, take it to Human Resources.

"BUT don't EVER give someone the satisfaction of taking you out of your calm which can result in you embarrassing yourself. Since that mistake, I don't take much personally. There is always going to be someone, something, that ruffles your feathers at work. Be like a duck and keep calm. Don't let anything get to you, and if it does, vent in private. Vent to your accountability partners, your friends, but NEVER, EVER at work."

Featured image by Shay M. Lawson

Originally published December 9, 2017

ACLU By ACLUSponsored

Over the past four years, we grew accustomed to a regular barrage of blatant, segregationist-style racism from the White House. Donald Trump tweeted that “the Squad," four Democratic Congresswomen who are Black, Latinx, and South Asian, should “go back" to the “corrupt" countries they came from; that same year, he called Elizabeth Warren “Pocahontas," mocking her belief that she might be descended from Native American ancestors.

But as outrageous as the racist comments Trump regularly spewed were, the racially unjust governmental actions his administration took and, in the case of COVID-19, didn't take, impacted millions more — especially Black and Brown people.

To begin to heal and move toward real racial justice, we must address not only the harms of the past four years, but also the harms tracing back to this country's origins. Racism has played an active role in the creation of our systems of education, health care, ownership, and employment, and virtually every other facet of life since this nation's founding.

Our history has shown us that it's not enough to take racist policies off the books if we are going to achieve true justice. Those past policies have structured our society and created deeply-rooted patterns and practices that can only be disrupted and reformed with new policies of similar strength and efficacy. In short, a systemic problem requires a systemic solution. To combat systemic racism, we must pursue systemic equality.

What is Systemic Racism?

A system is a collection of elements that are organized for a common purpose. Racism in America is a system that combines economic, political, and social components. That system specifically disempowers and disenfranchises Black people, while maintaining and expanding implicit and explicit advantages for white people, leading to better opportunities in jobs, education, and housing, and discrimination in the criminal legal system. For example, the country's voting systems empower white voters at the expense of voters of color, resulting in an unequal system of governance in which those communities have little voice and representation, even in policies that directly impact them.

Systemic Equality is a Systemic Solution

In the years ahead, the ACLU will pursue administrative and legislative campaigns targeting the Biden-Harris administration and Congress. We will leverage legal advocacy to dismantle systemic barriers, and will work with our affiliates to change policies nearer to the communities most harmed by these legacies. The goal is to build a nation where every person can achieve their highest potential, unhampered by structural and institutional racism.

To begin, in 2021, we believe the Biden administration and Congress should take the following crucial steps to advance systemic equality:

Voting Rights

The administration must issue an executive order creating a Justice Department lead staff position on voting rights violations in every U.S. Attorney office. We are seeing a flood of unlawful restrictions on voting across the country, and at every level of state and local government. This nationwide problem requires nationwide investigatory and enforcement resources. Even if it requires new training and approval protocols, a new voting rights enforcement program with the participation of all 93 U.S. Attorney offices is the best way to help ensure nationwide enforcement of voting rights laws.

These assistant U.S. attorneys should begin by ensuring that every American in the custody of the Bureau of Prisons who is eligible to vote can vote, and monitor the Census and redistricting process to fight the dilution of voting power in communities of color.

We are also calling on Congress to pass the John Lewis Voting Rights Advancement Act to finally create a fair and equal national voting system, the cause for which John Lewis devoted his life.

Student Debt

Black borrowers pay more than other students for the same degrees, and graduate with an average of $7,400 more in debt than their white peers. In the years following graduation, the debt gap more than triples. Nearly half of Black borrowers will default within 12 years. In other words, for Black Americans, the American dream costs more. Last week, Majority Leader Chuck Schumer and Sen. Elizabeth Warren, along with House Reps. Ayanna Pressley, Maxine Waters, and others, called on President Biden to cancel up to $50,000 in federal student loan debt per borrower.

We couldn't agree more. By forgiving $50,000 of student debt, President Biden can unleash pent up economic potential in Black communities, while relieving them of a burden that forestalls so many hopes and dreams. Black women in particular will benefit from this executive action, as they are proportionately the most indebted group of all Americans.

Postal Banking

In both low and high income majority-Black communities, traditional bank branches are 50 percent more likely to close than in white communities. The result is that nearly 50 percent of Black Americans are unbanked or underbanked, and many pay more than $2,000 in fees associated with subprime financial institutions. Over their lifetime, those fees can add up to as much as two years of annual income for the average Black family.

The U.S. Postal Service can and should meet this crisis by providing competitive, low-cost financial services to help advance economic equality. We call on President Biden to appoint new members to the Postal Board of Governors so that the Post Office can do the work of providing essential services to every American.

Fair Housing

Across the country, millions of people are living in communities of concentrated poverty, including 26 percent of all Black children. The Biden administration should again implement the 2015 Affirmatively Furthering Fair Housing rule, which required localities that receive federal funds for housing to investigate and address barriers to fair housing and patterns or practices that promote bias. In 1980, the average Black person lived in a neighborhood that was 62 percent Black and 31 percent white. By 2010, the average Black person's neighborhood was 48 percent Black and 34 percent white. Reinstating the Obama-era Fair Housing Rule will combat this ongoing segregation and set us on a path to true integration.

Congress should also pass the American Housing and Economic Mobility Act, or a similar measure, to finally redress the legacy of redlining and break down the walls of segregation once and for all.

Broadband Access

To realize broadband's potential to benefit our democracy and connect us to one another, all people in the United States must have equal access and broadband must be made affordable for the most vulnerable. Yet today, 15 percent of American households with school-age children do not have subscriptions to any form of broadband, including one-quarter of Black households (an additional 23 percent of African Americans are “smartphone-only" internet users, meaning they lack traditional home broadband service but do own a smartphone, which is insufficient to attend class, do homework, or apply for a job). The Biden administration, Federal Communications Commission, and Congress must develop and implement plans to increase funding for broadband to expand universal access.

Enhanced, Refundable Child Tax Credits

The United States faces a crisis of child poverty. Seventeen percent of all American children are impoverished — a rate higher than not just peer nations like Canada and the U.K., but Mexico and Russia as well. Currently, more than 50 percent of Black and Latinx children in the U.S. do not qualify for the full benefit, compared to 23 percent of white children, and nearly one in five Black children do not receive any credit at all.

To combat this crisis, President Biden and Congress should enhance the child tax credit and make it fully refundable. If we enhance the child tax credit, we can cut child poverty by 40 percent and instantly lift over 50 percent of Black children out of poverty.


We cannot repair harms that we have not fully diagnosed. We must commit to a thorough examination of the impact of the legacy of chattel slavery on racial inequality today. In 2021, Congress must pass H.R. 40, which would establish a commission to study reparations and make recommendations for Black Americans.

The Long View

For the past century, the ACLU has fought for racial justice in legislatures and in courts, including through several landmark Supreme Court cases. While the court has not always ruled in favor of racial justice, incremental wins throughout history have helped to chip away at different forms of racism such as school segregation ( Brown v. Board), racial bias in the criminal legal system (Powell v. Alabama, i.e. the Scottsboro Boys), and marriage inequality (Loving v. Virginia). While these landmark victories initiated necessary reforms, they were only a starting point.

Systemic racism continues to pervade the lives of Black people through voter suppression, lack of financial services, housing discrimination, and other areas. More than anything, doing this work has taught the ACLU that we must fight on every front in order to overcome our country's legacies of racism. That is what our Systemic Equality agenda is all about.

In the weeks ahead, we will both expand on our views of why these campaigns are crucial to systemic equality and signal the path this country must take. We will also dive into our work to build organizing, advocacy, and legal power in the South — a region with a unique history of racial oppression and violence alongside a rich history of antiracist organizing and advocacy. We are committed to four principles throughout this campaign: reconciliation, access, prosperity, and empowerment. We hope that our actions can meet our ambition to, as Dr. King said, lead this nation to live out the true meaning of its creed.

What you can do:
Take the pledge: Systemic Equality Agenda
Sign up

Featured image by Shutterstock

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