The Freelancer’s Bucket List

In the 2007 film, The Bucket List, Jack Nicholson and Morgan Freeman star as two terminally ill men who escape from a cancer ward and head off on a road trip with a wish list of to-dos before they die. In the process, both of them heal each other, become unlikely friends, and ultimately find the joy in life. Their list of things to do before they “kick the bucket” helps them approach their final days with a new lease on life, and they grow together as friends as well as individuals.

The message of the movie is a profound one. Life is short and you never know when you’re going to die, so why wait to do all the things you dream of doing until it’s too late? Translating this message into the realm of freelancing, the challenge becomes one of exploring all that the freelancing life has to offer and reaping the full benefits while in the midst of it, rather than looking back on this time with regrets.

In this post, I will share a few of my own personal freelancing bucket list items and encourage you to examine and begin pursuing your own.

Celebrate My Freedom

One of the main reasons I took the plunge into freelancing was the idea of complete, self-employed freedom. I could work when I wanted on the projects I wanted to and never have to report to anyone! Of course, it didn’t take long to realize that a successful freelancer often works much longer hours and more intensely than an employee ever does. It is an important pursuit to maintain the freedoms I set out to achieve in the first place. Although I don’t do it as often as I’d like, I want to celebrate and enjoy those freedoms at every possible turn.

Vacations, days off and time away are all potentially dangerous for the freelancer because any time we are not working we are not generating revenue. We don’t have paid vacations or sick days, so we have to manage our time off responsibly and carefully. Yet, we do still have the freedom to work wherever we want, depending on our technology needs.

Finding ways and places to get outside of the home office while still working is a key way to embrace these freedoms. A laptop at a local coffee shop, a notepad in a park, making business phone calls while taking a walk–these are just a few ways we can take advantage of our freedom to work when and wherever we want.

Another way to celebrate the freedom of freelancing while you can is to be a good boss and schedule your time off. I fail at this far too often, but disconnecting from work on a weekday afternoon or saving up to cover the lack of income while taking a vacation are important bucket list additions that we all should strive for.

Give My Family My Presence

For me, a huge benefit of freelancing is that I am home all the time, so I have the potential of being present in any and all family situations and happenings. The struggle I occasionally find myself in is that I can miss out on being involved in what’s going on at any given moment because I am working hard to meet a deadline or something else that comes up in relation to my work.

My family is the most important thing in the world to me, and they are the reason I work as hard as I do, but, as I have shared here before, if I spend every waking second working what is the point? My wife and children desire my attention and interest much more than my income, and although they appreciate how hard I work to provide for them, it is not what they want or need most from me.

While I am freelancing, I am determined to be present in my family. Dropping what I am doing for those that are most important to me is a bucket list item that I am constantly working to improve on.

Experience the World

I read an article recently about a web designer who telecommuted. One day he realized that he actually never dealt with his employer face to face, so he sold everything and moved to a foreign country without telling them. He travelled and explored different locations for months before his employer ever realized he was no longer living nearby! When I read this I realized it was within my realm of possibilities as a freelance web designer, and I’ve been intrigued with the idea ever since.

While I probably wouldn’t take the same route of failing to notify my clients of my departure, I have definitely added the idea of exploring and experiencing the world to my freelancing bucket list. My wife and I have always been a bit nomadic. Once our children are grown, we are planning to travel and enjoy the journey through other cultures and locations around the globe. I know far too many people who have barely ventured beyond their own state, much less to other countries, and I am determined to devour every ounce of life and its adventures around the planet while my freelancing lifestyle allows it.

What’s on YOUR Bucket List?

These are just three of my own personal bucket list items, and my hope is that they will inspire you to examine your own life and how you can experience it to the fullest. Freelancing can become all-consuming, so I hope we can all take a step back at times and re-evaluate what we are putting in and getting out of the choices we have made.

Have you made a “Freelancing Bucket List”? What are some items you are pursuing or have deemed as goals for getting the most from your life? Please share your thoughts, ideas and bucket list items in the comments.


  1. says

    This is a great idea, and not only for freelancers, but anyone who works, and tends to work too much.

    As I’m starting to grow my business now, I’m finding I’m spending a lot more time in front of the computer doing work that sometimes seems asinine to my boyfriend. One of the things on my ‘bucket list’ is to explain more of what I do to him, ie: why I need to writ blogs or keep updated on twitter or make a few changes in code.

    I think it’s helping me to understand that not everyone understands the freelancers way of life, and him to understand why during the regular workday I’m on the computer in my own zone listening to music.

    It’s not always about needing to take a vacation, sometimes it’s just a change in scenery. In a couple of weeks I’ll be taking care of my parents house and pets for awhile, and though I won’t be anywhere near my home and office, I’ll still be able to be productive, if not more so.

  2. says

    The story about the telecommuter packing it up and moving to a different country without telling their employer is pretty romantic, but I wonder what the implication from the tax code are… heheh!

  3. says

    The #1 thing I want to do before I die is take an entire year off of work (whether that be freelancing or employment) to just do ministry. I would love to travel the world ministering to children and teenagers!

  4. says

    Very inspiring! I’m about to make the leap into the freelance world and for the very same reasons. Life is definitely too short to spend your time playing the “what if” game. I’ve done that for far too long. Now I’m going to play the “why not” game =)

    One thing I want to do is volunteer my time and talent for a cause (without recognition). I did that for awhile (and on my own time). But when the agency I’m currently working for found out, I was told it wasn’t acceptable without slapping their logo on the project. I wasn’t doing it for exposure, so tagging a project for recognition was not cool to me.

    By the way…love the blog. I’ve followed for quite a while. Great stuff! Very inspiring!

  5. says

    1. Earn more money. Working on it.

    2. Get an iMac. Check. [2 weeks ago]

    3. Go out often. Yeah doing that already, almost everyday.

    Am i a fully satisfied man or what? ;)

  6. says

    My most …. biggest wish is to visit as many countries in the world as possible
    Untill now i visited like 12

    Also to enjoy a good life (financial security)

  7. says

    This is the list I made when I was about ten years old:

    1. See Stonehenge. (Check)
    2. See a total solar eclipse. (Check)
    3. See the pyramids of Gizeh.

    I have since added number 4: See a rocket launch.


  8. says

    As cliche and repetitive as it may sound, I want to see the world. I’d much rather see other planets, but that’ll never happen in my lifetime. As for where…as far and exotic as I can possible go. The Amazon is probably near or at the top of my list. Some other items include: see a great white shark up close, get good at amateur photography, learn kung fu, learn all of Buckethead’s songs on guitar, develop a mathematical proof that gets my name in a book, get to level 100 by myself on COD:WaW:NZ!!! *lol*

  9. says

    I love the Bucket List! It’s one of the most inspiring movies I’ve ever watched and being able to make your own bucket list will definitely boost your determination to work hard even more.

    My own bucket list:
    1. Study in Columbia or Yale as a Literature major.
    2. Become a veterinarian if #1 isn’t a possibility (I love animals).
    3. Visit Sparta.

  10. says

    After 30+ years as a designer, 26+ of those independently, there’s not much for me to really put on a Bucket List. I’ve done most of what I’ve wanted to do – including working remotely from different locations around the world, writing for major design magazines, having books published and more. My partner and I do have a desire to live in Portland half of the year and somewhere else the other six months. We’ve put it out there – so now it will be sure to happen. I tend to live/work taking the advice of my dying grandfather very seriously. He told me “Never say ‘I should have.'” The list is a great idea. If you don’t write it down, and/or speak it, it usually won’t happen.

  11. says

    Great post, sir! The story of the movie ‘The bucket list’ reminds me of a very sweet Indian movie ‘Dasvidaniyan’.

    All of us should have a ‘bucket list’ and explore this wonderful and colorful world, I feel! There’s so many good things to do before we all die.

  12. says

    Thanks to everyone for sharing your own lists and all your comments. I hope you all get the point here – not just to make the list, but to do it! Jeff Fisher’s comment is spot on. Unfortunately, most of the people I’ve met through life, even if they’ve taken the time to think about or create the list, have never set in motion the next step of making it happen. When confronted with what appear to be obstacles to achieving your dreams, start viewing those obstacles as hurdles and jump over them! It may take time, it will definitely take some risk, but the best question I think you can ask in this context is, “Why not?” Isn’t that better than reaching the end of your freelance career, or even your life, and sadly wishing you had done things differently? Go for it!

  13. says

    That film it way too good and it makes a great example for this case. In my opinion it is important to be aware of what we want in order to fight for that, no matter how difficult our situation might be. When it comes to starting a business for example, the only certain tip or advice will be related to the importance of a good business plan with the detailed goals to be achieved both in the short and long term.

  14. Annie Stith (@Gr8fulAnnie) says

    Hey, Brian!

    I guess I’m not technically a freelancer, as in choosing to work on my own instead of working in an office at a 9-to-5 job. Developing and then maintaining my website/blog will be my job because I can’t reliably stick to a 9-to-5 schedule due to chronic pain. But I feel so blessed that I’m able to work from home on my own variable schedule.

    The biggest thing on my “bucket list” is my website. As someone who’s healed from the effects of abuse from early childhood thru my late 20’s, I’ve felt called ever since to pass it on. That’s exactly what my website’s about.

    I’m also very fortunate to receive Disability Income so that I don’t have to rely on income from my website. I’m allowed to supplement my income (up to a point).

    This means my biggest dream comes true if, after the launch, I help a few people connect with the next Teachers they’re meant to find, or it becomes a thriving community, oor I’m able to turn it into a platform for my writing.

    If that’s not blessed, I’m not sure what is.


  15. says

    I love the freedom telecommuting gives you. I never completely moved away without telling my employer, but on a few occasions I’ve put in a day or two’s work from my vacation location a couple of days before my “vacation” began.

  16. says

    Great article and some interesting ideas. I always tell everyone that i’d never be able to go back to working in full-time employment because of the “freedom” I have. But having read your post I’m not sure I’m making the most of being a freelancer at all. At the moment I work 12 hour days and just stress far too much. A change is needed I think! Thanks for the realisation.

  17. says

    I’ve only been freelancing for 5 months, but I’d love to be able to work and travel at the same time. I have the travel bug big time and the world has so much to offer, so even if it’s just lots of cheap 2 week backpacking working holidays, then that would be the dream!

  18. says

    Ashley – I am glad Im not the only one!

    I would include traveling the world to study different forms of design. I took a Design History class awhile back and it was very interesting to see where we all came from!

  19. says

    great article. I have not watch the movie, but I will surely look for it. As I take on photography, I really really want to travel a lot. As for design, I’m about to take the biggest leap of my career, to take my full time job as a designer to another level. This has been my biggest fear and I hope, I’m capable enough.

  20. says

    I’ve been working freelance since April 2007 and never looked back. I actually hate going to the office and I hated my supervisor back then.

    Now I can travel while working. As long as I have my plug-it internet or free WIFI in the location, I can work whenever I want to.

    I did this many times without my client’s knowledge and it never affected the quality and timeliness of my output.

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  22. says

    Experience the world is on my list. I spoke to a couple the other day who are travelling the world running a social networking business writing blogs, twitter updates and creating facebook pages. Sounds like a good life.

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  24. says

    It’s been a very difficult week, and next week doesn’t look much better. One of the biggest projects on my list is to set up a live webcast of my cousin’s son’s wedding. He is getting married here, and my cousin is out-of-state. She is dying of cancer and can’t come to the wedding.

    Between this, and your blog, you’ve really made me think: What else do I want to accomplish? I just celebrated the fourth anniversary of my business and have met many goals. Now I’m going to spend some time this weekend filling out my bucket list. Thanks for the inspiration!


  1. The Freelancers Bucket List…

    In the 2007 film, The Bucket List, Jack Nicholson and Morgan Freeman star as two terminally ill men who escape from a cancer ward and head off on a road trip with a wish list of to-dos before they die. In the process, both of them heal each other, beco…

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