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The Freelancer Life – Is It All Worth It?

Sometimes I wonder if everything that I do, everything that we do, is worth all the trouble. I’m tired of trying so hard, I’m tired of being what I want to be, I’m tired of all the failures, all the problems, all the conflict and the confrontations. This isn’t supposed to be what it was like.

* * *


When I quit my 9 to 5 job, I didn’t know what would come next. My plan was travel the world with my entire $20,000 savings. That was 2010. After years of soul-searching, of reading up on society, of understanding and embracing our world, I realized the 9 to 5 wasn’t for me. I wanted freedom and I found a way to make it work.

I quit my job, built up a solid blog and a social media following. I learned everything there was to know about online marketing and ultimately came to be known not just as a travel blogger, but also as a travel writer with more than a few guides under my belt. I upped my freelance writing game getting my byline in print in the UK, Canada, Australia and the USA. Now I work a handful of different jobs every week: writing, marketing, blogging, tweeting—maybe they’re all related but they’re all a bit different from one another, too.

And it works for me. I have a few regular jobs which bring me in an a regular income, more than I made working 9 to 5 in an entry-level, out-of-college publishing job. I’ve learned the ropes of digital content creation, of running a monetized blog, of travel writing and of PR and marketing. And while it works for me, I can’t help but wonder: is it all worth it?

Always Working - The Freelancer Life

Working, not sightseeing #oops

I chose an uncommon career path because I thought it would allow me more freedom of movement, more freedom of expression. Basically: just the opportunity for MORE. But since doing this for a few years now, I’ve realized it’s all a bit of a myth. Sure, it works to a degree. I certainly have more freedoms and maybe even more opportunities than if I was working 9 to 5. But at what price? There are many challenges and problems that I didn’t expect. Ones I certainly haven’t been prepared for.

Instead of dealing with corporate bureaucracy as an employee trying to do things a little differently, I deal with all the bureaucracy of owning a business—on my own. With no one to turn to when I have a problem or a question. It’s all me, all the time. I run every aspect of my own business from the writing to the marketing to the technical side and the business side. It’s not easy (which probably makes sense or else more people would be doing it), but this new way of working—is it really worth the trouble for all the supposed freedom I get from working independently?

I get asked about one hundred different favors a week. I’m not exaggerating here. I’m counting the requests that come in through Facebook, the emails, the press releases, the tweets, the WhatsApp messages from friends and the follow-ups. All the follow-ups. Everyone wants something. All the time.

Anyone who has tried to make it as a writer, especially as a blogger, has probably faced the same. And I’m not just talking about my generation here. It’s not often that someone in a creative field gets the full amount of respect, attention or dignity that he or she might deserve.

I honestly don’t know if it’s all worth it. Maybe for some people it’s an easy choice. But I look at all that I have to do to survive, and I sometimes wonder why I do it all.

Adam Groffman

Traveling, trying to relax in Seville and not worry about work

Our lives have become more segmented; our jobs too. That’s why we rent our extra bedrooms out on AirBNB, or shuttle Uber users around in our cars every weekend. Our governments have failed us. Corporations have failed us. And we’ve let them ruin not just our lives, but our society. It’s become more and more difficult to have just one job anymore. One job isn’t always enough to live on.

We’re told that we all have special skills or extra commodities, things we could monetize. We’re told there are lots of ways to make money, online and off. We’re told so many things about the way the world works. But I’m not so sure we’re better off because of it. This parody video (see below) highlights the ridiculousness of some of what we’re doing. It’s sad, really.

The video talks about privilege, but are problems are actually much deeper. We’re often told to go out and follow our dreams. Hell, I’ve probably said it myself on Twitter more than a few times. But, in reality, following your dreams, especially if it involves entrepreneurship, isn’t easy. This article on Quartz, by Aimee Groth, summarizes it nicely:

“Following your dreams is dangerous,” a 31-year-old woman who runs in social entrepreneurship circles in New York, and asked not to be named, told Quartz. “This whole bulk of the population is being seduced into thinking that they can just go out and pursue their dream anytime, but it’s not true.”

So while yes, there’s certainly a lot of hard work that goes into building something, there’s also a lot of privilege involved—a factor that is often underestimated.

I don’t always know what I’m doing. And I certainly don’t always know how I’m feeling. But I look at what we’ve got in the world today—people preaching the value of quitting your job, of leaving it all behind, of following your dreams. And I worry. I worry about those less privileged than myself who swallow this up. I worry about the state of our society. What are we doing to our world, to ourselves? Is it all worth it? I don’t have an answer. But I think we need to make sure we ask ourselves regularly. A status-check on our lives and on our futures.

  1. Robert says:

    A really interesting article, Adam! It’s not often I find blog pieces so engaging but this really poses a lot of questions and a lot to think about.

    Personally, whenever I ask myself these questions, I come to the same answer: just do what you genuinely feel will make you happy. This is partly to do with the point you make when opening the final paragraph, that you don’t always know what you’re doing. And that’s true of everybody. There are so many unknowns in life that I truly believe most of the time, most people don’t know exactly what they’re doing (or indeed how things will turn out!) So just do what makes you happy I say.

    Sure, things might go to crap, but if they do deal with it when it happens. Don’t let fear of an unknown hold you back from doing what you want to do. You’ve only get one life and no matter how long any one life might last, nobody has time stay stuck in a job/city/relationship they hate etc. I do understand I’m speaking from a pretty privileged place myself, but I can honestly say I think I’d say the same even if I wasn’t.

    • Adam says:

      Hi Robert, Thank you for chiming in here. I wholeheartedly agree with the sentiment that we should do whatever makes us happy, but sometimes our happiness is constrained by society or other external pressures. (ie, I want to do what will make me happy, but current financial situations make that pretty difficult… I can manage, but, it’s just not ideal for my happiness…)

      And yes – I agree to not let a fear of the unknown hold you back. It’s important to take risks and go after what you want. And worry about the consequences (to a degree) after the fact!

  2. So well said, Adam. I feel the same way. On the outside, people think we are living a dream. Living in paradise. But, it isn’t true. Working for ourselves is incredibly hard and can also be incredibly isolating. The grass is always greener, and while I don’t think I could go back to a 9-5 job, I also know I yearn for a day where I don’t open my emails, check facebook, schedule posts, respond to requests, etc. It is exhausting and when you’re the sole person doing it, it is even moreso.

  3. Oh Adam. It sounds like you just need a big hug. Of course we always have tough times and doubt ourselves.

    It’s especially hard when you’ve got all the pressure of running a one man-shop. You’re a writer, salesperson, marketing manager, PR whiz, social media promoter, travelling guru…and at the same time you have to do the day-to-day things of eating, cooking, sleeping, house chores etc. No wonder you get worn out.

    Friendship can also be hard to find and develop. When you’ve achieved the success you’ve had, you’re bound to have lots of people wanting things from you. Favour favour favour. Nag nag nag. You end up wanting to avoid people, but know that you need them to earn your living.

    Is it all worth it? That’s for you to decide yourself. Your gut feeling knows.

    In the meantime, it seems like you’re a bit burned out. Have you considered taking time out. I mean real time out. No laptop. No phone. Just go to the mountains or something for a long walk. Maybe day, maybe a week.

    Write a post beforehand, put an out of office on your email, plan it ahead. And go.

    Then you might be clearer about whether it is all worth it. Or what you might need to change.

    Hope that helps. Big hugs!

    • Adam says:

      Hi Alex – thanks for the virtual hug :) Your list of all the things I have to do including housework/general life stuff is spot on – and it’s stressing me out just reading it!

      And it’s funny, before I even published this I had put up an out-of-office and that’s been a simple way to just make myself feel better! Next step is to try and take an actual holiday away from my phone and all my responsibilities…

  4. Kim says:

    Thank you for sharing this. It’s refreshing to see an honest look at what the realities of freelancing are really like. I wonder: Is it ever possible to shut off the world for even an hour (outside of normal sleeping hours that is) to regroup and refocus given the number of demands?

    I ask because I’ve recently launched my own travel blog dedicated to two-lane roads. I won’t dare say I fully understand the challenges though since it’s new and certainly not monetized. This blog is slow to get going because financially I just don’t have the resources to travel as often as I’d like.

    Still, it’s been worth it so far to me because it took me five years to finally decide on a niche that works and is one I like. At this juncture I just can’t even see writing full-time as a freelancer, though the thought has crossed my mind a few times. Posts like these are a huge help in figuring out that decision, even if it is still a ways off. So again, thank you.

    • Adam says:

      Hi Kim – thanks for your insight. Society does seem to put so much pressure on us that even the thought of an hour away from the connections I’ve got seems daunting and scary. Maybe that’s a sign that I really need to find a way to disconnect. It’s important to take a step back from whatever you’re doing every now and then, take a breath, and just reset your mind…

  5. Mel says:

    Wow this really resonated for me. Im working on a similar post right now, something about living someone elses dream… I just moved to chiang mai to do this whole thing full time, and i find myself stressed, staring at my laptop all day, wondering if its worth it. Honestly, i was happier working in a bar. Because i could talk to people, be on my feet, be useful. Because a bar shift ends and you go to the beach. A bar shift pays well enough (in aus) so you save it all up then have an adventure for a few months. Total freedom. But the crowd here seem to believe the freelance thing is freedom…. And i call huge BS. It never stops. For some, its worth it. But i am processing these very same questions you pose, and i cant thank you enough for such an honest post. I have funded my travels for four years with casual season work and fun backpacker jobs… And digital nomadicy is no where near as enjoyable nor as free. The bigger picture looks great but the day to day reality i find dull. I will keep going, but quite frankly an adventurous, restless, people-person nature-lover has no place behind a laptop screen… Isnt that why i left London in the first place? So thanks for this. Its refreshing not to see another laptop on a beach and be told to chase my dreams. My dreams are up moutains and in oceans… Not hidden in the glare of my smart phone. Freedom is relative.

    • Adam says:

      “living someone else’s dream” <--- that! I miss the days of being able to shut off the idea of work after a shift ends. I also like what I've got now, but finding the balance between both has been a big challenge. I am definitely not a digital nomad and actually get quite upset when people call me one! Also, I love your last bit in the comment about not including a photo of a laptop on the beach. ALSO not my dream! :)

  6. rebecca says:

    Grass is never greener. Great read. Try and look on the bright side. Sometimes there is never an answer for absolute happiness, sometimes we just need to learn to be happy with what we have… and improve from there. Hope you find what your missing :)

    • Adam says:

      Thank you Rebecca! You’re right that it’s all about happiness – I am certainly happy with the life I have now, but sometimes I have doubts. And you’re right: the grass is never greener. It’d be good to not compare our lives to those of others – that’s where the problems start.

  7. Megan Eileen says:

    I’m really glad you wrote this Adam. I’ve been feeling the exact same, especially this week and it’s great to know that I’m not alone. You’re doing awesome though, so keep doing what you do (as long as it makes you happy)!

    • Adam says:

      Thank you Megan!! I’m always impressed with what you’re doing, too, so it’s great to see your comment here. And yes: it’s always all about what makes you happy!

  8. Kemkem says:

    This is a great post Adam. I wish more young people would stop and ask themselves the same question from time to time. I see a lot of bloggers selling the dream to others. I always say the same thing when l see the mommy bloggers urging everyone to have kids. Misery loves company :-) . I worry because l see a lot of people swallowing this kool-aid and quitting their jobs. It’s a hard thing to do, so many hats. What worries me even more is that people are not thinking ahead..namely retirement..401k. I guess you can do it till you’re 70 or something, but the constant pressure. I am glad we had no internet per say years ago, and l worked a 9-9 job for lots and lots of years which is enabling me to travel now. Delayed gratification you might say, but worth it. I feel so old because l want to say “at least work till you have enough credits for social security”. It’s going to get really ugly for a lot of people. I will share…hopefully, some will get wise. Hang in there! You’re welcome to come recharge your batteries in Seville with us. Do absolutely nothing but play with the dogs, hang by the pool and play ping pong! :-)

    • Adam says:

      Hi hi Kemkem, So nice to hear from you and read your comment. There’s a lot of kool-aid in the digital world and I don’t think enough people stop to think about what they’re doing. It’s so important to be even the tiniest bit rational (even if just on occasion). I agree the future looks pretty dim for many young people—and not just those of us trying to be our own entrepreneurs or work self-employed. Society has a lot of problems and we’ve created a lot of problems for our future. Who knows what’s going to happen??

      I think a holiday outside of a big city and in the wilderness is maybe just the thing I need to recharge batteries. Thank you for the invitation :)

  9. Sam says:

    Oh, Adam. I hear you. Zab and I were just talking about the pursuit of money today. I’ve realised lately that I’m really not motivated by money and that if I have enough to live the way I do, that’s OK…but at the same time it would be nice to have more, right? The idea that I “should work more” and be aiming for something bigger, more ambitious is so deeply engrained in our society that it’s hard to just be happy with the status quo.

    I think what I really wish is that money simply didn’t exist and that people could devote themselves to self-improvement and the search for meaningful and satisfying work for the greater good of society. So basically, I’m a communist and I wanna live in the Federation of Star Trek.

    • Adam says:

      Hi Sam – thank you for this comment! “Should I work more” sounds like a terrible phrase. I want to work less, not more! But I do what I have to do to survive and hopefully my dreams will catch up with my reality (or vice versa???)

      Oh, and can I live in your dream world? Sounds fantastic.

  10. Kerwin says:

    Hiya Adam.

    I hear you and yes it’s worth it.

    I “work” more than I ever did at my Corporate job now, but I love every minute of it. And I was a constant worker in Corporate life.

    Sometimes we don’t realize how good we have it. As we are knee deep into it.

    It’s good that you are getting 100s of requests weekly, some of us get nothing… And are constantly, looking for opportunities and getting turned down although they’d do a fine job if given a chance.

    Just take it in strides young man and enjoy every minute, capitalize on every opportunity.


    • Adam says:

      Hey Kerwin – thanks for your comment. I do try to enjoy every minute and I am oh-so-thankful for where I’m at today. But, as some of the commentators below have noted, it’s still a challenge to find the right work-life balance. As a freelancer/entrepreneur, that’s been a real challenge. But I’m still working on it :)

  11. Meg Ten Eyck says:

    Oh the feels! I can absolutely relate to this. One day I hope I can be as successful as you are Adam. It’s nice to know that it’s not just me. Sometimes the world of blogging seems to be filled with tons of smoke and mirrors. Transparency really helps.

    • Adam says:

      Hi hi hi Meg! I think anyone who works independently and for themselves has these same kinds of thoughts. It’s just not something everyone talks about :/

    • Pragya Raj Sapkota says:

      Dear Meg Ten Eyck,
      I want to know what is successful?Success is in your feet whatever you do .First thing you have to try to perfect in any one profession.People are not completely perfect in any work. Great desire makes men crazy if it could not fulfill.So Travel in long journey it gives satisfy to you as well as gives refreshment to the human.Thank you

  12. Jessi says:

    Phew, I feel you. The process of being true to myself and pursuing my dreams has come with a price tag. I think it’s the same for everyone in my position, but that cost doesn’t get talked about a lot. I’ve lost my security, my stability, my free time, and my marriage, all in the name of making it. I don’t regret a thing, but I’d be lying if I said I didn’t feel as though I were drowning sometimes. It’s not just hard work. It’s hard emotionally, physically, and spiritually. There are definitely days when I wonder what the hell I’m doing with my life, and whether its worth it.

    Thanks for being real. Sometimes we all need to hear that we aren’t alone!

    • Adam says:

      Hi Jessi – thanks for you comment. Everything comes with a price tag but a lot of times we don’t discuss it but rather only speak of the positives. It sounds like you’ve paid quite a hefty price to build the life you want to live, but all power to you for sticking with it!

      And realness forever!

  13. Ryan says:

    That just mean that you don’t have the gut/strength for it. No offense. It’s not made for everybody :).

    • Adam says:

      Hmm, well personally I think a little self-doubt brings clarity and precision, so until I figure things out I’m going to continue asking the questions :)

  14. Anne says:

    Hi Adam, just wanted to thank you for writing this.

    As a fellow freelancer I share a lot of the same thoughts about running my own business. The constant requests and favors…oh, the favors! Sometimes it seems like I’m on a hamster wheel that never stops spinning…or beating my head against a wall wondering if this is all worth it or if I should consider changing course.

    But whenever I really have a bad day, I think back to feelings of dissatisfaction and loneliness in a seemingly glossy, very well paid corporate career (one that I left for travel and freelancing.) I’m grateful to have had that experience to reflect on. Putting myself back there helps me regain perspective. And when I do that, it does feel worth it.

    Still, you’ve posed some excellent questions and reminders. (And that video is hilarious, btw.)

    • Adam says:

      Hey Anne – interesting to hear your story. The job I left for this life abroad, though, was one I actually really loved. And I know I was on a good path in that life but just needed to shake things up. I don’t regret the decision but every now and then I do wonder what life would’ve been like had I kept at it.

      For me, it’s still this idea of freedom that I assume will come eventually that keeps me moving forward with my freelance plan

      And yep – I’m obsessed with the video. Ever since I stumbled on it a few months ago I’ve shared it with everyone I know!

  15. christina leigh morgan says:

    amen! I left the corporate world 10 months ago to pursue travel blogging and freelance life full-time and definitely have a lot of questions about the value. being able to be anywhere at anytime is great — having to work from everywhere at all times… less so. (especially in the newbie building phase). the experiences, amazing — having them alone… well, you know.

    thanks for sharing the lesser-revealed side of the coin!

    finding balance seems to be the most important part of the ride. :)


  16. Katie says:

    Great post Adam. You sum up a lot of the reasons why I chose NOT to try to make it as a freelancer at the end of my RTW trip. I didn’t want to have to feel like I was always hustling, always working, always wondering where my next paycheck was going to come from. I felt like the idea of “working for yourself” was somewhat of a myth because you’re always working for someone else, either an employer or a client. I prefer the stability of a single employer even if it means giving up some freedom.

    And I enjoy my 9 to 5 job, even when it sometimes means some long hours. I have a great boss and good benefits and good vacation time (by American standards) and I feel like what I am doing is the best use of my skills. The things I am best at and have the most experience with don’t translate well to freelancing, at least not right now (eventually I could probably start consulting, but in my field I would need a lot more experience to be successful at it).

    I feel like there’s this myth out there that you either work a soul-sucking corporate cubicle job or you work for yourself, when really there’s a lot of in between. I was miserable in the job I left before my RTW job but after I came back, I got a job doing literally the exact same thing, just for a different employer, and that made a world of difference.

    • Adam says:

      Thank you Katie – I appreciate that coming from you. I have to admit I wasn’t really made for the constant hustle and it’s been a real challenge at times. I also really did enjoy my 9 to 5 as well. I remember working as a designer and lots of friends spoke about their dreams of owning their own design firm, while the idea just never really interested me. And yet here I am with my own business (though it’s not in design), oops!

      There’s definitely a myth – and quite a few vocal people advocating for a life that doesn’t even truly exist for them.

  17. noel says:

    I feel that going freelance without a baseline of work or income stream can leave to a stressful life. It’s a slow building and experimenting process filled with sacrifice and the key is experimenting and seeing how the new media world leads to better opportunities. For me – I’m happy to have a decent income stream non travel related and any revenue I generate in the travel space is just cream on top.

    • Adam says:

      Noel – excellent point! A lot of the most successful freelancers and entrepreneurs start with a bit of seed funding (whether it’s through investors or their own personal wealth), and it’s not often discussed. I’ve been lucky to have started this whole blogging/freelancing project at a time that worked well for me, but I still wonder if the amount of time/effort I put into it is worth it all. I love what I do but when it starts to feel too much like work, it gets more and more difficult.

  18. Ngaire says:

    I totally hear ya. I’ve just finished travelling for close to 8 months and figured freelancing would be the way to go (I’m a designer and web developer). But really, is freelancing worth it? I’m still trying to figure that out as I go for a mix of applying for jobs and networking my skills. We’ll see what happens. I guess the main thing is happiness. Try one if it doesn’t make you happy, do the other. Life is short right?

    • Adam says:

      Hi Ngaire, Thanks so much for commenting. Definitely agree taking risks is important and trying for your own dreams/goals. It’s almost equally important to question those goals and see where it leaves you then.

  19. Nikki says:

    I enjoyed reading your post! It was an interesting read because you’re right, everyone lusts over the freelance lifestyle and leaving the 9-5 job. I am fully freelance and a travel blogger and yes, it is difficult at times, but I do think it is always worth it and I am always 10x happier than I was chained to a desk. That’s the thing–yes, it’s daunting to run a blog and be a freelance journalist, it’s stressful to worry about money, it’s crazy to be traveling to a different country every month—but when I remember sitting at an office from 9-6pm day dreaming about being elsewhere, wishing I could be paid to do what I love to do rather than writing for a few hours at night–I definitely think the freelance lifestyle is worth it!


  20. […] The Freelance Life: Is It Worth It?, Travels of Adam– Adam shares some hard truths about what it’s really like to be a freelancer, especially overseas. […]

  21. Stefan says:

    Hi Adam, I was thinking about your post and just want to share a thought: My feeling, while reading your post, was that you phrase your questions “too big-scale”. For instance, I think you should review whether working freelance fits to your personality – and answer this question without immediately connecting it to your travelling. After you have this answer, you can ask yourself more questions. For example, you could review what it is that you get out of travelling and which ways there are in life to achieve this. When you have answered your smaller questions, you could possibly create a model that fits to your needs… I think that that big question “Is this all worth it” is harder to answer than smaller questions, maybe even not at all. All the best to you!

    • Adam says:

      Hey Stefan – great advice, thank you! Definitely important to start figuring things out from the ground up. Excellent idea!

  22. Job at home says:

    I’m not sure why, but your article seems very pessimistic. I personally through time learned to love the struggle that comes with being your own boss. Yes, it’s tiring and hard at times but at the end of the day I think it is worth it. Much better than sitting and doing nothing. You have to be grateful for all the opportunities given and not worry whether or not someone has it better than you, and of course always strive for more. Keep in mind that most of the times people give up not because the circumstances are wrong but because they’re not motivated and driven enough.

  23. […] nails on the head entitled There’s No Such Thing As A Free Lunch. Adam of Travels Of Adam also penned a few practical thoughts about what blogging and freelancing affords him and whether it’s a worthwhile lifestyle to […]

  24. De'Jav says:

    well written piece. I’m sure living the unconventional life has paid off. Someday s you may wonder to yourself but I’m sure there are many more good days than bad with the flexibility to do you.

  25. Hi Adam

    Thanks for writing about your blogging journey since 2010 and it’s up’s and down’s. I’m on the starting up phase of blogging, my first published post was on 25/10/2014. I’m just taking a break from applying for writing jobs!

  26. will says:

    Nice to read a real post Adam. I have to admit for me the freelance travel life isn’t for me. Yes I have weeks/months where there is nothing I want more but to get on a plane and fly away but as you said it’s quite a hustle and I do enjoy my 9-7…. sometimes

  27. Carlos Parra says:

    At the end I really didn’t get his point. Just because his post 9to5 job wasn´t easy, it wasn’t worth it? Maybe he expected something and got something else in return? Happens to the best of us.

    Also, seems like he is not delegating some of the stuff he does. I’m not talking a batallion of employees, just 2 or 3 people handling the backend and other things he doesn’t want to do.

    And also, why not look into establishing some passive income with wise investments. Not big ones, but with time and the money he’s making, some passive income might be possible and oh so great. That way, he’ll have extra time and money to pursue other things.

  28. Ross McNeal says:

    You are being cynical with the word freedom. It is a word that has so many meanings depending on who and were you are in your life. You need to be specific about “your” definition of freedom.

  29. Baffled says:

    Sorry but …What are you complaining about? You sound like a whining spoiled baby. You were not happy about your 9 to 5 job and now you’re complaining about your job not being 100% fun 100% of the time? But tell me, which job is fun and easy all the time? Who taught you this? And on top of it you go as far as questioning if it’s ‘worth it’?Man you have a job, money, food in your plate, a bed, and you travel. Check your privileges and show some gratitude seriously.

  30. Bobb says:

    The grass is always greener elsewhere, that’s the silly human nature. I suppose this is exactly why the concept of ‘practicing gratitude’ is trending so much right now, people lose sight of everything they have and and take them for granted. Such a shame! Even though as a freelancer I do have hard times ( working unpaid, clients paying 3 months late, insane paperwork, the lack of stability, a lot of bills to pay in advance until the client pays me back months later etc), I know I have to stop whining and be grateful that I do what I love, work with interesting people, travel, and basically make a living out of my passion, and I’m not chained to a desk forever with the same people which sounds like the definition of hell to me.
    TLDR: Gratitude man, gratitude.

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