Skip to main content

17 first job regrets you can actually avoid

No one gets a first job do-over, but here are some things people wish they’d done differently.

17 first job regrets you can actually avoid

No one really knows what they’re doing at their first job, so it’s easy to make rookie mistakes, usually ones you’d never have thought of. You might avoid one or two by reading the regrets of seasoned workers looking back at their very first jobs.

Here’s what they have to say:

“I wish I'd set better boundaries. My boss took advantage of me here and there because I had a hard time saying no.”—August Freirich, assistant editor

“My biggest regret from my first job was not taking opportunities to pick up new skills when I had a chance to do so. I was too afraid of a steep learning curve or asking too many questions during the training process. I have learned to speak up and express more of an interest in learning new things, regardless of how many questions I may have along the way.”—Marissa Lasoff, administrative services coordinator at Paragon Solutions, Inc.

“I feel I jumped at my first job offer without truly knowing what the job entailed. I should have investigated the requirements of the job, the population of the school and town, as well as speak up for help when I felt I needed it.”—Tara Kfoury, Ph.D., urban middle school teacher and instructional fellowship coach

“My biggest regret is probably not taking full advantage of being ‘new’ and people assuming I didn't know how to do things. I was in such a rush to demonstrate my abilities and ‘fake it until I made it’ that I was missing learning opportunities that I could have had if I had just admitted that I had no idea how a particular task or process worked.”—Kevin Cochran, technical director at NBCUniversal

“I would have asked the question ‘how would you define success within this role?’”—Kayla Gaudette, admissions counselor

“Throughout school there were companies that I idolized and worshipped. When I got out of school I thought I could get a job there and move up the corporate ladder right away. The reality is, with a popular company, it is hard to do that, especially without much experience. Everyone is in competition for the same position. I learned I needed the opportunity for trust, growth and experience.”—Lindsay Egan, surf school director at Ocean House Surf Shop

“I wish I had looked for a job with more structure that I could build tangible skills in. I got a lot of experience but there wasn't a lot of structure or support to be able to build my resume up with great skills.”—Shannon Sweeny, public relations specialist at Babson College

“I took a job that paid me far less than what I was worth and required that I worked far too many hours. It was a great experience and I met amazing people, but I stayed on for almost a year and a half. If I were to do it all over again, I would have bailed as soon as it stopped making me happy.”—Vanessa Calaban, legislative researcher at Massachusetts Municipal Association

“At my first job I really lacked self confidence and I believed that I had to be perfect at everything so that I wouldn't get fired. While it is important to me to do well and work hard, I wish I hadn't given such high importance and stake to that first job. Part of me knew it was a dead-end job but my lack of confidence kept me from reaching out to do more, to build myself up or increase my resume. I wish I had been more confident to try new things and apply to more jobs, especially the ones I didn't think I was ‘good enough’ for. First jobs are important learning opportunities but are not the definition of who you are or what your success story will be.”—Marina Crouse, freelance writer and graduate student

“Not taking enough initiative and having pride in my work, no matter how menial it seems.”—Morgan Hendrickson, production assistant

“Technically, I had my first job for two days before I quit to accept a much better offer. In retrospect, I probably should have either committed to the first job I accepted or waited on accepting until I got both offers. Since it was my first job offer, I got excited and accepted it without thinking about the timing of my other offers.”—Jonah Ollman, associate producer at Time Inc.

“I was overconfident and I would have put in more effort. I learned I wasn't invincible.”—Katelyn Hollenbeck, post production coordinator on The Middle at Warner Bros.

“My first professional full-time job was with the Department of Defense as a journalist/public affairs specialist. On my first day, my supervisor told me that there was never a need to make waves and that if I had any difficulty on the base to go to him first and not HR. Now, I'd tell him that his behavior was inappropriate and most likely illegal and would report him to my advisor so that his behavior would be registered with some kind of authority person.”—Suzanne Hinton, director, office of academic engagement and community action and part-time faculty at  Emerson College

“I wish I had set boundaries around my personal life from day one. It's too easy to start thinking you need to sacrifice your work-life balance in order to grow professionally. I would have established those limits early on and stuck to them.”—Tanya Braun, currently ‘funemployed’

“My biggest regret from my first job was not being more organized in my goals and falling short of some ideas I had prior to starting the job. What I wish I could do differently was set a more realistic time table that I could have followed to periodically check in on the progress I was making toward goals. ”—Chris Esber, chief medical resident at The Ohio State University Wexner Medical Center

“My biggest regret is not voicing my interest in moving up in the company enough. This went hand in hand with my second biggest regret, which was not being proactive about meeting with my manager on a regular basis. If I did it all over again I would set up a weekly meeting with my manager and have open conversations from the beginning about what it takes to move up in the role.”—Sarah Herczog, event manager

“Even if you know you're the best at your job, try to stay at your co-workers’ level for the first two weeks. I was alienated almost immediately by my new co-workers when I didn't take breaks or work at a slower pace with them. If I could do it again, I’d wait until after those initial two weeks because that’s when you understand the normal conditions so it’s OK to outwardly shine at your job.”—Ryan McCullough, U.S. Navy

Like what you’ve read? Join Monster to get personalized articles and job recommendations—and to help recruiters find you.


Back to top