Career real-talk: What it’s like to work for yourself or someone else

At the beginning of 2016, I made a big change. You may remember when I wrote this post about how I started working in the fitness industry, or about how I turned my blog into my business, and in reading those posts you may assume that this Lady would never have a desk job again working for someone else. Well, I did end up going back to the the corporate world. I didn’t see it coming either. I thought it would be fun if we did some digging into that change, while at the same time try to give you some insight that can help you gain perspective on your own situation — learning from someone who’s taken both paths. (Edited to add: I ended up leaving this full-time role in March 2017 to go back to being a freelance and contract worker … but the details are still important, so read on!)

These days, I’m working in a regular full-time office gig. The job requires me to drive to work and sit in traffic about 45 minutes on the way there and just under an hour on the way home (it’s not accessible via the BART/subway/public transportation — or you can bet I’d be on there with my backpack). I pack all my foods for the day and schedule my life outside of those working office hours. And during the work day, I have to force myself to get up and walk around the office complex just to get in some steps, because I’m not teaching multiple classes or working at the gym all day, giving me tons of movement organically.

Career real-talk: What it's like to work for yourself vs. someone else by A Lady Goes West blog

Making big changes in my job world

Last year at this time, I was working mostly for myself. Between writing A Lady Goes West, doing freelance writing for various websites and two fitness instructor jobs, I was booked solid, but I was doing it on my own time. It was a real hustle. It wasn’t easy. But it had a few good things going for it — for instance, I never had to worry about my activity level being too low during the day, that’s for sure.

Where I’m at now is such a big transition from where I was then, it seems like I owe you guys an update — most importantly because I am in a unique position to give you insight on what it’s like to work in two very different environments.

Going from freelance to full time

But first, some backstory, because you seem to want to know more about what I’m doing. While I had no intentions of heading back into the corporate world, my current job is pretty cool in that it’s all about my interests. Basically, I’m in charge of a blog on a big scale for a big company, focused on healthy living, fitness and wellness — I get to travel to L.A. frequently to manage photoshoots (and sometimes be on camera), and I learn a lot from the interesting people we profile. Oh, and did I mention I already worked for the company as a group fitness instructor before taking on this new role? Perfect match, right?

When all the wheels were in motion for my current gig, it all just seemed to fall into place quickly so that I could make the big change. Over the course of a couple of weeks, I ended ongoing freelance relationships, put in my notice for a few classes that I was teaching, found a dog-walker for Rudy and readied myself for a huge change in my life. I have to admit, even though I had spent many years of my post-college life working a regular corporate job in public relations and communications both in Orlando and San Francisco, I was super nervous to head back into this environment. Yet, don’t you know … it’s like riding a bike.

I definitely get to do some fun stuff in my role. However, most days, I’m just a regular office worker like everybody else trying to maintain a healthy lifestyle and a social life. (Want to see what I’m up to? Visit the site, where I’m the editor.)

What it’s like to be in an office every day

But let’s be honest, there are times when I’m at work and I scroll through Instagram and see my blogging peers having a picnic in the middle of a Wednesday with fresh home-made salads, which they’re enjoying after a mid-morning workout class with friends, wearing fabulous new activewear and sporting a tan. I look down at my linty black pants, reposition my crossed legs and try to get back to focusing on the task at hand on my screen, knowing that I miss my poor puppy at home, who is being walked by a hired dog-walker in the middle of the day. That photo-worthy life is not in my reality anymore on most days. And maybe it’s not in yours either.

Unless you have a very flexible schedule, a sales job requiring you to go to different appointments all day or a telecommuting role that gives you the ability to multitask and bounce around, you’re chained to the endless emails in your inbox, meetings and responsibilities, and you probably don’t get to make a nice lunch in your own kitchen every day either. You also likely don’t get to dictate your own schedule as you please. But you know what, you probably have a job with many perks that you may not be appreciating. And that’s what I’m here to remind you about today. No matter the path you’re on right now, I bet it has some good things going for it.

Even though it seems like working for yourself is all sunshine and roses (it may look like that on some blogs and on Instagram), there are definitely pros and cons of each situation. Now what I’m about to do is talk in general terms, and this isn’t only about working for yourself as a blogger, it’s about doing your own thing overall. Because I’ve gone back and forth between both situations and have a unique perspective, I thought you’d like to see this based off my own experiences entirely. You never know what works until you try it for yourself. You know? Let’s do it …

Pros of working for yourself

  • Make your own schedule. Pretty clear: if you don’t feel like working, you don’t have to.
  • Travel. Travel. Travel. You are in charge of your own vacation days. You can go anywhere you want, when you want. You don’t have to skip a holiday with your family because you’ve run out of days off and you’re needed in the office.
  • Work wherever you want. Whether it’s a coffee shop or your bed, it’s up to you.  Nobody is looking for you over a cubicle wall at set hours.
  • Take on as much or as little as you want. You can say no to projects if you feel overloaded. There’s no one telling you what to do.
  • Ability to make as much money as you can work for. How hard you work is hopefully how much you get paid for. Which means if you really go for it, you can make extra income.
  • Make your food at home. Okay, this may not be on everyone’s list, but seriously, it’s on mine. The lunchbox and food-packing situation is terrible when you eat like I do. I have no less than five containers each day. And the food I eat is best prepared on the spot, but I make it a couple of days in advance to save on time, and it’s just never quite as wonderful. (Which reminds me, I should do a “What I Ate Wednesday” soon.)
  • Idea generator. You get to be your own creative director and come up with all your own ideas, with the ability to pursue your passions and focus only on what interests you.

Cons of working for yourself

  • Make your own schedule. There’s a chance nobody is expecting you to be anywhere, and sometimes that’s a sad feeling. I remember waking up on Monday mornings when I didn’t have to teach a class until the afternoon realizing I had a bunch of writing work for myself to do, but didn’t have to get out the door, so it would sometimes be hard to get motivated to do it. It’s easy to get motivated when you arrive at an office on Monday morning, away from your home and into your work. Real easy.
  • If you don’t work, you don’t make any money. When your business depends on you, you always have to be on. Nobody is going to jump in and do it for you.
  • Vacations are not paid. Even though you may have the flexibility to go where you want, there’s a good chance you aren’t getting a regular salary to be off the grid, unless you’ve set up some awesome passive-income streams (and if so, props to you!).
  • No benefits. You have to get them on your own. And that’s pricey.
  • Ability to make only as much money as you work for. If you don’t do a good job with a project, you probably won’t work with that client again. You constantly have to find new business, sell yourself and put in the work.
  • Idea generator. You have to be your own creative juice and creative director and sometimes your inspiration dries up. Sometimes you just want someone to tell you what to do.
  • Lack of community. While the blogging community is an interactive one, and in other industries there are co-working spaces you may be able to go to in your own city to collaborate, you have to really make an effort to find a group of peers when you work for yourself. You’re a lone wolf out there otherwise.

Pros of working for a company

  • Regular paycheck. A large bi-weekly paycheck (with taxes already taken out) that comes no matter what is an awesome thing.
  • Benefits. Paid time off. Benefits. Paid time off. Benefits. (Unless you’re lucky enough to be married, like me, so your husband’s company provides.)
  • Community. Although offices have their ups and downs, you’ll likely make some casual friendships at the water cooler, that you’re not likely to have working on your own or from home. That sense of belonging is actually a pretty big deal. And if you have a work spouse, well then you’re golden.
  • Working on things bigger than yourself. You get the opportunity to learn from others and try things you may not try on your own.
  • Resources. Oftentimes working for a company gives you bigger resources for projects and you get to pool your efforts to try large-scale initiatives. (And you say words like “initiatives” when you work in an office too, as well as other slightly annoying corporate made-up terms like “level up” and “circle back.”)

Cons of working for a company

  • Flexibility. You’re bound to your job and office hours and you have to fit your fitness and life in early mornings, late nights and weekends. And sometimes you probably get the Sunday blues. And when you have to sneak your workouts in early mornings or late evenings, your leisure time is minimal Monday through Friday.
  • Limited vacation. I’m guessing your company doesn’t give you as many paid days as you want to take off, so you have to use your time wisely. And if you have family that lives across the country like I do, well it’s tough.
  • Having a boss. Depending on your personality, it may be tough for you to have someone telling you what to do all the time. But then again, if you have a good boss, it can be awesome.
  • Pay is pay. While a regular paycheck is good, unless you have a commission or bonus-based job – no matter how hard you work, your paycheck stays the same.
  • Time. If you work a full-time job, you have to make choices and sacrifices. I work out significantly less now, teach only a couple of classes and write A Lady Goes a fraction of the time (and yes, I miss checking in each day with you all! I really do!). My days are super-scheduled and full, and it’s not always easy to live that way without very much free time to do things like take my car for it’s check-up or try out a mid-day workout class. 

Overall, right now the choices that I’m making in my job are right for me, but it’s definitely not a walk in the park — especially because I had lived a different kind of work-life for several years doing my own thing and working in fitness.

I could talk about this topic forever, and based on the questions I get, I know this is something on your minds. When people write to me and say they aren’t happy with their full-time job and want to do something else, I usually tell them to pursue their passion as a side hobby while keeping their full-time gig, so a small amount of income is being generated by the new “project.” While you’re doing that, save up some money and make a business plan before going at it full time. It’s not going to be easy. And it’s not always going to be Instagram-worthy, but it may be worth it one day.

Tips for you for where you are right now

  • Write down what you love. Is there a way to make money from it? Is there an idea you want to turn into a business? Research it thoroughly and see if it’s worth pursuing. Could it just be a side hobby and give you enough fulfillment that you’ll be fine keeping your current job?
  • Meet with other people who are in the industry you want to be in and pick their brain. Make connections and ask real questions about what you should know.
  • Make the most of your current job. We can’t always spend our lives wishing for the next big thing, I bet there’s a chance you have a lot to appreciate about the situation you’re in right now.
  • Take a class. Do you have time for some side-education? Either weekend fitness trainings, cooking classes or photography classes. Try to get inspired by things outside of your daily job and see if that fills you up.
  • Volunteer or join a group. Do you need to meet new people and get your mind off your daily work? Try finding a nonprofit that needs help or a charitable organization where you can use your talents and gain perspective.

I get a lot of reader questions on this kind of topic and plan to address it more in future posts. If you have any comments or questions, please leave them below, and I will try to address them soon. But for now, BRB, gotta head to work. 🙂 

Real talk: working for yourself vs. someone else. What you should consider ... #blogging #freelance #work Share on X

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  1. This is a super relatable post and that envy does strike, looking at mid-day pictures of people just hanging out! There are certainly pros and cons to each lifestyle. And I think it’s important to remember that no matter what lane you’re in, nothing is permanent. If you’re unhappy with the 9-5 lifestyle, changing that can happen so easily. But trying new things and new lifestyles is a part of life itself!

    Danielle @ afloat on a full sea

  2. That is such wise advice to do what you love on the side, if you aren’t really happy and fulfilled in the full time job, because it keeps the income steady, but you are also able to use your gifts. I love that you’re working for a company that does align with your interests; it was fun to hear about you made the transition. 🙂

  3. You know the saying that the dream doesn’t come without the hustle? (or whatever it actually is).
    This is a great post, Ashley. You are going to succeed at anything you attempt, so no wonder you are doing so fantastically in your new position!

  4. I love hearing more about your job. I have to ask because I’m curious but have you noticed anything bodywise going from teaching numerous classes a day to working out once a day ? I work at a chiro office which is definitely not my passion but the closeness and flexibility makes it worth it for now,

    1. Ha, Heather! That’s a great question, and one that I think may deserve it’s own post. The answer is YES. Glad you have some good flexibility in your current role! Thanks for reading. 🙂

  5. I love your tips for getting into something you’re passionate about. I’m a PE teacher, so I’m definitely working in the field I enjoy (health and fitness), but when I’m home over the summer I’m always wishing I could work from home. I would love to hear more about how you got the confidence to teach adults group fitness. I have no problem talking to a group of children, but adults scare me. I’m certified but have yet to teach any classes because I keep putting off looking for jobs, mostly because of my nerves.

    1. Hi Patricia! Yes, teaching adults is the only thing I’ve ever done, and it’s scary at first. Well it’s always going to be slightly scary, because you are in front of a large number of people in some classes. But when it comes to fitness, if you KNOW what you are doing, people are so nervous themselves, you have to be the strong one when you get in front of the room. It’s actually a fun feeling to know you are helping others. You can do it too, lady!

  6. I absolutely LOVED this post and getting some insight into your thoughts on career situations. Thanks so much for sharing!

    And I second the idea of bringing back a WIAW post soon!


      1. hahahahahhahahah DYING from that. I totally get it. I wish we were both on a lovely picnic in the middle of the work day looking fab. But for now … 🙂

  7. Great post Ashley! Having been in the corporate world my whole life and now being a freelancer/student this past year, I can totally relate to every bit of this. There are days I would like to go back because freelancing is not as easy as everyone thinks it is. I’m at peace being where I am right now and reevaluating next year after I pass my board exams. I’m sure what’s meant to be, will be.

    1. Totally not as easy as it sounds! I know you’re experiencing all new things now that you’re off on your own. Keep up the hustle, Megan! You’re doing great. Thanks for reading!

  8. I liked reading this. I’ve worked as an editor in the medical education field since I graduated college 6 years ago, so it’s all I know! I, too, struggle to fit in the “life necessity” stuff and to keep up my energy to make it to the gym at night after an hour commute home. I’m in the process right now of starting a compression socks/gear company, and my dream is to work for myself doing that and working on freelance writing/editing projects (and maybe even starting a food/lifestyle blog). But – you have some good points. Both sides of the fence really do have their ups and downs, so I’ll keep that in mind for whatever path I can ultimately take.

    1. Hi Traci! That’s so cool you have an idea for something and are already working on it. Keep up the hustle, lady! And — yes, the struggles of fitting in workouts while having a commute are not fun. But maybe that’s not your reality forever. 🙂

  9. Thanks for sharing this post! It’s great to hear your perspective since you have done both! Now that I’m staying at home I always wonder what I want to do once I go back into the workforce. I get a little taste of “working from home” now with teaching stroller strides and doing my rodan+fields stuff…. but it is tough to stay focused at home- that’s for sure! Your new job sounds awesome btw!

    1. Hi Marielle, Well it sounds like you are keeping busy with your two endeavors, in addition to parenting. Maybe some opportunity will present itself to you when it’s your turn to head back into the workforce in a different way than you currently are! 🙂 Thanks for reading, lady!

  10. Great post Ashley! There is a lot of talk about the future, and all of us moving towards a “gig economy” which would essentially be everyone freelancing. Right now, it’s a fantasy for a lot of people, and it’s helpful to hear the pros and cons! I’m lucky to be fairly flexible in my corporate job – even today I waffled about working from home but ultimately decided to go in, because I knew it would be sort of a lonely Monday in my apt alone! Hopefully we can find the best of both worlds one day 😉

    1. I love that your job gives you so much flexibility, Jill! That’s super important. And the gig economy is an interesting thing — definitely starting it up in the Bay Area of course. Here’s to finding the BEST of both worlds for us when we need it hehhe.

  11. I really loved reading this post – this topic has been such top of mind for me lately! Things haven’t been the greatest at work but it is good to be reminded me of all the positives. Right now I am looking at building up the side hustle and see what happens from there!

    1. Hi Danielle, no job situation is every going to be perfect, that’s for sure! 🙂 But yes, always hold onto the positives when you can. And if you feel the scale tips to the negatives, you know you need to make a change. Thanks for reading!

  12. Love this! I recently went back to working a full-time job after working for myself for over a year. It’s tough! I definitely miss certain things about working for myself, but some things, like a consistent paycheck and benefits are much better with a full-time job. The tough part for me is learning to enjoy the full time job and make the most of it! Great post, Ashley! 🙂

  13. Ashley, I very much love and appreciate this post.
    You’ve nailed a lot of the reasons why I’m very happy to keep blogging as a hobby. It may afford me some excellent opportunities, but I really appreciate the comfort of my full-time gig, and I have a great full-time gig that affords me the opportunity to travel and have a great life outside of the office.

    1. Hi Ange! I think it’s awesome you are so very sure that you are only blogging as a hobby — it gives you the ability to do only what you want as a blogger and not have to make money with it. Keep up the excellent work with your blog and day job, lady!

  14. Yet again, another post I love. I definitely fall into the comparison trap when reading blogs and I loved how you wrote that sometimes you will scroll through IG – I totally get jealous of people being outside or working out in the AM. This post was so helpful in that real-life (if you work a corporate job) means a scheduled life and food that may not be super yummy on day 3 of leftovers. I really struggle with that when I read blogs as I’m always trying to find the balance. They can workout or have what I perceive as more free time to do things. I’m a teacher and feel like my I’m constantly pushing to make life outside of work happen.

    I’m most curious about the meals you make for the week, how you find balance in the scheduled routine of the week (is that ever hard for you?), and how you relax.

    1. Hi India! It’s a constant struggle! And I’m always wishing I had more free time — but I try to keep my weeknights TOTALLY free, except for teaching a class or two. I use the evening times to go for a walk with my dog, eat dinner with the hubs and then watch TV and go to bed early. When I’m well rested, it makes everything easier. And I DO NOT answer work emails after I leave for the day unless it’s an emergency, because that gives me space to regroup. I will totally talk more about this soon. Keep up the great work with your job. I know it’s tough, but you are making a difference being a teacher! And as always, thank you for reading. ?

  15. Hi Ashley! This is such a great post! I kept nodding the entire way through – I GET IT. As you know, I went from dancing and working in fitness to blogging and working in fitness and now, well, I work in fitness full-time, but I’m not teaching. I LOVE my job, but it makes keeping my blog up a real challenge. This makes me sad because I LOVE blogging, too. I can totally relate to the cons of working for yourself. After we moved to NY, I had all the free time in the world but couldn’t find a thing to write about. I didn’t really feel like I had a purpose or responsibilities. Now I have more than I know what to do with, lol. Such a great read! xo

    1. Hi Heather! Yup! It’s tough to maintain a blog when you have a full-time job, that’s for sure. But hopefully you’ll find a balance that works for you. And I know how busy your job is about to get having worked at a new OTF myself heheh! But it will be fun for you too. Keep up the great work, lady!!

  16. Hey Ashley, thanks for writing this. I think that in life it’s so easy to have the “grass is greener” mentality always thinking maybe it would be better to live somewhere else, or have a different job or look a different way and the reality is there are pros and cons to everything, including being an employee and working for yourself (or office vs more flexible work).
    I used to have a corporate job (regular paycheck, commute to the office every day) and could totally relate to everything you wrote about. Now I am freelance and am kind of going through work changes now that are stressing me out. I guess it’s best to do what you can with what you have and if you really don’t like it or want to try something new, go for it! Enjoyed this one 😉

    1. Hi Diane! I know! Work is stressful no matter what, but we just need to try to get into the best situation possible for us and try to enjoy it. Good luck to you in getting through the changes in your freelance work! As always, thanks for reading!

  17. I remember leaving my 9-to-5 around the same time as you went back into the office and you gave me one tip that I still continue to use everyday… “Make sure that you get out of the house everyday.”

    The main “con” that I’ve found is that working from home can be lonely, especially so if you’re like me and make writing your full time gig. Sometimes I have to push myself to get out the door, but it definitely keeps things from getting too repetitive.

    Great topic and insights!
    XO, Jessica

    1. You bet! You have to get out and interact with people, or it is totally lonely. I’m glad you remember my advice hehe! Hope all is going well in your new situation, lady! Well, not all that new now!

  18. What a great post! I don’t think anyone can make a choice that you have unless it fits THEM…having seen both sides you know what is working for you right now. I know blogging can’t be easy and worrying all the time about whether you’re writing captures people and the work your doing will pay the bills would be so stressful (for me at least) but then going to a corporate job , You’d miss that ‘free’ time you talked about during the work day! The great thing for you is that you have done both so you could always go back and I know with the energy and positive attitude you have, any employer would be lucky to have you!

    1. Thanks so much, Fiona! It’s definitely helpful to have a perspective of both things in order to appreciate all situations! As always, love that you read and comment!!

  19. Really enjoyed this post! It’s great that you can see the pros and cons of each. We often want what we do not have but only see the sunshine and rainbow side of it! I’m working toward being my own boss and having the flexibility I’ve craved for years…its a lot of hard work! Great post–its a reminder and a word of encouragement to me today as I try to work toward my passions while still appreciating my current situation!

  20. Fantastic post Ashley! I would love to see a WIAW on a normal work day and would also really like to hear more about how your transition to less workouts is going, both physically and mentally. I’m just curious because I’m in a similar place in my job in that I can’t bust out the daily workouts I once could when I had more time. Thanks!

    1. Hi Erica! It’s tough to manage it all and try to be really healthy too. I know! And the changes in my job have changed my food and workouts a lot. I will definitely dive into this more soon, because it seems it would be a good topic! Thank you so much for reading and commenting. And keep up the good work in your own life and job!

  21. I’ve never worked for myself, but I do know that I depend highly on social interaction and I get a lot of motivation from my colleagues. I don’t know if I would get lonely/a bit stressed out with having to create social time for myself everyday!

    1. Hi Dani! Yes, socialization is super important and that can be hard to do when you’re home alone working! So glad you like your new job, by the way! 🙂 Have a fab weekend, lady!

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