Summary
Your career impacts every aspect of your life, and it’s crucial to make moves that align with your values while embracing the flexibility and risks unique to your twenties. This episode is designed to help you feel better about job hopping, the decisions you’re making in your career, and how to know if it’s time to change jobs so you do know where your career is going. Wherever you’re at in your career journey, it’s important to make sure your job is adding value to your life outside of your career and not taking away from it.
Key Takeaways:
- Understanding how your career influences your overall happiness, lifestyle, and personal values
- Recognizing the signs that a job isn’t right for you and acknowledging the impact it can have on your mental and emotional well-being
- Explore different career paths in your twenties to set yourself up in your thirties
- You need to network before you want to job hunt
- Your career goals can evolve over time, focus on what you want right now
Is it bad to job hop in your twenties?
No — and it won’t tank your resume as much as you think. Employers have gotten more understanding since 2020, especially with shifting remote-work policies. As long as you can talk about what you learned at each stop without trashing a past employer, hopping around is actually a good way to figure out what company culture, management style, and work setup actually fits you.
How do I explain job hopping or a messy resume in an interview?
Frame each move around what you gained or learned, not what went wrong. Avoid bashing a previous employer — speak to your strengths and what each role taught you instead. Interviewers respond to confidence and clarity way more than a perfectly clean timeline.
How do I figure out where my career is going if I don't have a long-term plan?
Stop trying to map out the next 30-40 years. Focus on the general direction you’re headed right now — what you want in this season of life — knowing that direction can and will shift as your life changes. A rough sense of “here’s what I’m working toward currently” beats an overly detailed plan you’ll probably abandon anyway.
Want support around your career path? CLICK HERE to see if coaching with me is your next best step!
Related Episodes
Ep. 99 Take the career risk with Somer Dice
Ep. 9 You Can Change Your Mind: Career Edition
Ep. 8 What You Need To Do To Up-level Your Career with Kate Hutson
Ep. 95 Leverage Your LinkedIN with Katie McKiever
Ep. 83 Speaking to Your Strengths: LIVE Coaching Call with Orien Dalton
Transcript
Where is your career going?
Happy New Year, happy first episode of 2025 and welcome back to another episode of how to twenty-something with today’s topic being all about your career
For the vast majority of people, January is a time where people start to think about what they want from the next year of their life and it also happens to be the longest, most depressing month of the year where these 31 days really feels like 6 months
And because the days are short, the weather’s cold, and the holiday hype is over, you start to get unhappy and, dare I say, fed up, with certain parts of your life that probably haven’t been working very well for quite some time, you’ve just been distracted since Halloween with all of the fall and winter festivities
To no fault of your own, I think we all fall into this trap at some point and I know for me, my first year at my big girl job it really came into effect about how much i hated the place I was working at
I started that job in august of 2019 and by January of 2020 I was updating my resume and applying to new places because it really hit me with how miserable I was at this job
Basically, I lasted 4 months before I was like yeah no I hate it here
It was so far less than ideal from what I wanted for myself
It was in a satellite office where I was the only employee aside from a part time retired man named Nick, who was overly overly happy and if you’ve ever met someone who lives in Celebration, Florida, Disney’s town, then you would know what I mean
It’s like extra level, borderline creepy, happy
But anyways this job was also doing work I had no interest in, retail design, and if anyone knows me they know that I am not a shop til you drop kind of girl
I save my annual mall trip for black friday and then I call it a day and don’t return until the next year
So yeah, I was desperate for my first job out of school that I was willing to take anything that was going to give me a chance
And by January, I was ready for a new job to give me a better chance
Mind you, I had no idea what I was doing, how applying for jobs really worked, or that a global pandemic was going to interrupt this job search just a few weeks later
I didn’t know what I wanted from my career, how to appropriately job hunt, literally nothing, just that I needed to get out of where I was currently working
But also knew I was trapped to the city I didn’t even want to be in, Orlando Florida
I say trapped because I was in the middle of a lease, and had bought all new furniture and didn’t really know where else to go nor did i have the funds to pick up all of my belongings and move somewhere else
This is also no hate if you do happen to live in Orlando, I just never wanted to and I also think to some extent I knew that the job I accepted would determine a lot of other factors in my life, but, like I said, I was desperate for the first place to give me a chance
And that came in the form of this less than ideal job for me, but because I felt stuck I didn’t really know what else to do besides ride it out and hope it got better, while also applying to other jobs in the surrounding areas
You see, my clients come to me for help around the decisions or potential changes they want to make in regards to their career and usually how that decision will affect some other part of their life
It’s always, jess I need help with my career and x, whether that be relationships, boundaries, time management, habits, health, you name it
I’m a certified health and life coach, nutrition coach, and personal trainer and am the one stop shop to helping any young adult get their life together and feel confident around the changes and transitions they want to make in their career
And those transitions can be from one job to another if you’re feeling dissatisfied at your current place of employment, it could be from one industry to another, and even leaving the corporate world altogether to go do your own thing
I personally experienced all of these different moves by my 25th birthday and created a system to help other twenty-somethings do the same in their respective lives without losing their marbles in the process
So today’s episode is to help you with your relationship to your career, how it influences your entire life in your twenties, why you shouldn’t feel bad about job hopping, and overall as the title would suggest, developing a better understanding as to where is your career going
And if as you’re listening to this episode you’re thinking, but how do I know now is the time to leave my current job, then please head to the show notes and download my newest favorite resource: 3 signs it’s time to change jobs and how to start making moves
All you have to do is click the link, put in your name and email and check your inbox for a pdf
But let’s start with your relationship to your career and why it’s so important to make any risky move now, while you’re young, rather than try to stick it out and hope it gets better
I mean seriously think about it, if you are part of the twenty-something population who is not married and has no kids then you are only responsible for yourself
So any risk you take is on you, no one else will be affected by your decision and there is a lot less at stake because you don’t have a mortgage or a family to think about
Which also ties to if you’re unhappy with your current career whether that be the actual work your doing or your place of employment then you need to stop hesitating and change things up
Again because you are only responsible for you it also means that you are the only one responsible for your own happiness
Besides, and this is something I constantly have to remind my clients of, because you’re in your twenties, time is on your side
You have time to mess up, to change paths, to start over
So why not try something different right now if you don’t currently like what’s happening in your career
Your job influences just about every part of your life at this age
It determines where you’re going to live, and therefore who you’re going to be surrounding yourself with both at the office and out in the real world
It determines your schedule which then influences the times you’re available to work out, your days off, what networking groups or happy hours you can attend and so on and so forth
It even can determine when you can sleep and eat like if you have a graveyard shift or are a night shift nurse
Your career choice determines whether there is a busy season and when that season is each year
It determines your stress levels and your mood, literally your entire life
Which is why it’s so important to feel aligned with not only your career path but the company you are choosing to work with as well
And I’m not saying all of that to worry you or stress you out, but to remind you that this is a decision that should be well thought through and if your job starts to take away from other parts of your life then it’s time to seek out a different opportunity
Because, I want to remind you of this very important paradigm, your job should enhance the life you want to live outside of it, not take away from it
Which is also why I tell people it’s okay that they are hopping around to different jobs
I know it does not look great on a resume to show inconsistency and variability as in you keep jumping around and aren’t staying loyal to a single company
It shows you as someone who is not trying to grow with the company and that you’ll leave the moment someone offers you something better
And that can leave potential employers a bit hesitant to hire you
But as long as you can talk about what has happened on your resume and speak to your strengths or what you’ve learned, WITHOUT bashing a previous job, then typically they become a bit more understanding
This is something my clients and I will role play a lot on, how to speak to their strengths so they don’t leave an ambiguity in an interview based on their resume
And maybe you’re thinking, but how would I even get to the interview if the employer doesn’t like my resume, as in why would this potential future employer even give me a chance
To which I would respond with, 85% of job acceptances comes from knowing someone
So yeah, applying through indeed and sending your resume into the internet void is most likely not going to get you an interview since Ai is going to filter you out before human eyes even have the chance to say yes or no
You have to have to have go through your network as the world is very much who you know to even get to the part of what you can do
But I actually think it’s good for you to hop around in your twenties, you need to experience different company cultures, different styles of management or whether something is completely remote versus hybrid versus in office, even different types of work
So that by the time you’re in your thirties you do know what you’re doing with your career and set yourself up for career and financial stability in the long run
Now, I’m not saying you have to job hop or it’s necessary to get a feel for different places, it’s more so to help you feel better about your resume if you do have a bit of a choppy one
Whether you’ve hopped around my choice or not
I personally think it’s absolutely ridiculous to pick a career path when you’re 18
When you have no idea what jobs are out there, what you have an interest in, and what you want to spend a majority of your time doing and thinking
Yes, some people get lucky and do know exactly what they want to do with their life and continue to stay on that path, but for the vast majority of people, that just doesn’t happen
A Federal Reserve Bank of New York paper found that 27% of college graduates work in a job directly related to their college major
27 percent, meaning 73% are not
And I believe that is due to cities having wider opportunities that encompass a broader range of degrees, as well as 18 year olds picking a fucking career and are expected to stick with it
But also on the topic of job hopping, the working world climate has changed a lot since 2020
We were expected to adapt to a new norm when everyone was working from home and now that we’re a few years out, companies keep changing their work from home policies and expect everyone to return back to the old norm
And a lot of people are not willing to do that because we’ve learned more about work life balance and how much time we get back in our day by being able to work from home for at least half of the week
But because policies continue to change, employers are much more understanding of a choppy resume, again as long as you can communicate and confidently talk about your path
But the pandemic changed a lot of companies so it makes sense that you’re still jumping around trying to figure out what aligns with you the best
I talk to people who say they have to be in office and that office culture is a deal breaker and then other conversations where people want to be completely remote and that’s their deal breaker
And it doesn’t help that companies keep changing their work from home policies so if it no longer suits your needs, then allow me to be the one to tell you that that is a good enough reason to change your place of employment
And to know that going from one job to the next or one industry to the next, within less than a year time frame is not going to kill your chances at getting hired by somewhere else
Now, if you are someone who is listening to this and has been at the same job for over three years, and or you’re in the field you studied, then kudos to you and please don’t think you also need to job hop
Because if it ain’t broke, don’t fix it
If you’re company is providing you with opportunities, you like the people you work with, you’re being compensated appropriately year in and year out, and you don’t feel like you are wasting your time or having your soul sucked from you, then yes stay where you’re at
At the end of the day, everyone is going to have drastically different career paths
It doesn’t mean someone is doing something wrong and someone else is doing their job right, it just means it’s okay to be different and to not feel bad about wanting something else from your career
But when it comes down to where your career is going, I don’t want you think about the next 35-40 years of your life
That’s way too far out in advance and we don’t even know what the state of our country or the world will be in, what life experiences are going to occur along the way, and literally every other detail that can and probably will change your career
So instead of overshooting your entire career path until the day your retire, I want you to think about your career right now, in this moment and the general direction you are planning on taking it, knowing that you always have the decision to change your mind
For example, do you want to work your way up the corporate ladder and does your current company allow for that?
I have a client who just left her job and part of the reason for that is because there were no growth opportunities
The sector she worked in would prioritize external hirers over internal moves because they wanted a fresh brain in the mix instead of the loyalty and trust from a current employee
Which is so dumb on that company’s end, but that’s besides the point
How it affected my client was that it made it very difficult to move around and move up in the company
So she knew that in this moment of her life, her current place of employment is not going to provide her with the opportunities she’s after, so she’s changing her path
Maybe you’re someone listening who is working until you’re married and then you plan on being a stay at home wife and later mother or a stay at home husband and father
I’ve had conversations with clients where they tell me they just don’t want to miserable in their job right now, but they know they plan on leaving it within 5 years or so
And maybe you’re someone who is in your career right now to be able to get out of the corporate life and do your own thing
That’s what I did for myself, and that’s also a conversation i have with some of my clients
To which your job should not be interfering stress wise with your business endeavors outside of it
For me, I accepted my second job out of school with the mission to eventually get out
It didn’t create a lot of stress in my life, the hours were pretty consistent, the work I was doing was mundane, the people I worked with were amazing, and so I was able to stay there until my lease was up, save up as much money as I could, and make that transition to my own business
In 2020, I knew my career path was going in the direction to help me leave and at the time be a personal trainer
So then it became a matter of how do I make this other path work incongruence with this current one so I don’t burn myself out
But in 2019, my career path was to keep my head down and do what I was told
I wish someone helped me with my job hunt and stick to my values and non-negotiables of my career
However, I also know that everything happens for a reason and if I didn’t have the shitty first job after school then I never would have lost my job, taken the time to become a personal trainer, discover what passion and fulfillment really is, go back to the corporate world and plan my exit through originally health coaching and be talking to you right now on this podcast about your own career paths
I became the resource i so desperately needed and feel every twenty-something needs, and honestly even I still need at times, because my life was an absolute shit show and it took a lot of stumbling around before it all clicked
And now I do know where my career is going at least for right now, I know that this year I want to do more paid speaking events, I know that next year I plan on starting to write a book, I know that I plan on coaching for as long as I can, while also knowing who I coach might change as I change and my own life story develops
Knowing where your career is going means having a general direction of what you’re working towards right now, not having all of the details finalized or even an exact 5 year plan
Because you never know what surprises life is going to give you – both on good and bad ones
And regardless of where you want your career to go or knowing what that looks like, it’s important to make decisions that feel good for you and are aligned with what you value the most
And then also leaving a situation when it goes against your own values
And that’s how I’m going to wrap up this episode of how to twenty-something
If you just listened to this and need some help with the direction of your career, then please don’t hesitate to reach out to me via email, instagram, or directly scheduling a call with me using the link in the show notes
And if you liked what you heard or know someone who does need to hear this, then please pass this episode along, post it to social media and tag me at coach.jessdiamond so i can share my gratitude
Otherwise this does conclude another episode of how to twenty-something and as always, I can’t wait to be in your headphones again next week with another brand new episode