» Forums » Freelancers » Re: From decades of traditional work to freel...
Page options
Community Member

From decades of traditional work to freelancing? Share your experience

Over the years, Community members have mentioned giving freelancing and Upwork a try after decades in the traditional workplace or as a way to ease into retirement. Some had already retired and decided to use freelancing for supplemental income.


When you have a career that spans multiple decades with vast experience in various roles and industries, how do you choose what to add to your Upwork profile, what to leave out, and what to save for specific proposals? 


We’d love to hear more about your experience and any tips you may have for others navigating similar situations.

~ Valeria
Community Member

I joined Upwork around 2015/16 after cutting down to part time as I eased into retirement. It's worked out well for me.


It's quite simple. My Upwork profile includes my relevant experience in writing, editing, and medical terminology.  It also includes the difference between editing and proofreading and what I don't do (formatting, cover design). I tailor my cover letters to the client's specific needs (I don't answer vague ads that don't specify fiction/nonfiction, subject matter/genre, only if they invite me to apply.) My profile wording is rather long, but it's worked well for me (and many clients have copied my description for use in their ads).

Thanks for sharing your experience, Bettye! I’m glad to hear this is working out for you well. 

I like that you include a few sentences about what you don't do and what would essentially be outside of the scope of your work. I've seen other Community members do the same to help set boundaries and expectations for clients. 

~ Valeria

You make fill high focused since it's my first time am involving in this job.Bettye thanks for  loading your experience 

Community Member

Honestly, few clients spend much time perusing a profile on a site like Upwork. I started here when it was Elance back in 2007. Lots of changes through the years, and yet one thing has remained consistent: you win or lose work based on your cover letter, how you address the specific points of the job description, and your work portfolio.

I advise people to get the first 2-4 sentences of their profile concise and clear. Add all the experience and job titles you want, but it's more noise than anything else here.

That's not to say it wouldn't be vital off platform, as in approaching prospects directly, but with Upwork, you're not impressing anyone with a long-winded profile.

Gerald, I suppose that was one of the questions I had in mind when I started this topic - is there any harm in a longer profile description? Especially for those professionals who have a lot of experience they could include. Thanks for sharing your advice and approach. 

~ Valeria

I think Gerald is absolutely on point.  The quality of your response to a job description in your proposal is what matters most.   If you can hit on the vital point(s) - either what is there or what is missing in the description - that shows the client immediately that you know what you are doing.   After that,  your job history probably means the most to clients, and lastly your profile.    I do work in a field (MS Office development) where credentials are less important, though.

Looks like Upwork is going hard after the retirement gen -- must be some $ to be had.


I would be careful what you ask of this lot Valeria - as you might get some stinging answers and opinions that could upset your senstivities and challenge some of the more questionable policies and tactics of UW (e.g. I share my understanding of the 'private feedback' mechanism with lots of colleagues in this demographic....they all give me aghast responses and ask why I would tolerate such nonsense.  I tell them it is one ugly thing in a sea of average where an occassional attractive thing happens). 




 We generate revenue from both talent and clients, with a majority of our revenue generated from service fees charged to talent for access to our work marketplace, Upwork 10-K Feb 15 ,2022.


I have to disagree on the importance of a good profile (though not necessarily a "long-winded" one). I get most of my jobs via invitations, including invitations to join talent clouds, and often go for months at a time without having to place any bids. That wouldn't happen if I didn't have a good profile, and I know that clients do read mine because they usually mention specific things as the reason that they've contacted me.

Just to clarify: My specific profile is longer than I'd ideally prefer it to be not because I'm trying to impress anyone (my 100% Job Success Score, Top Rated status, and less than 24 hours response time are sufficiently impressive on their own), but because I was tired of getting invitations for one-stop publishing, including everything: ghostwriting, editing, proofreading, formatting, and designing a cover, or for writing jobs that pay a penny a word. I also wanted to clarify the difference between proofreading and editing for a public that largely believes they are one and the same. By addressing these, I have cut down considerably on  invitations I'm not interested in. As I said, it's worked well for me. I do, however, agree that the first sentences/paragraph of a profile as well as a cover letter should be clear, concise, and attention-grabbing. 

Community Member

Valeria,  this is such a tall order! 


"Easing into retirement" has never been less easy!  These days, many of us don'r retire. We die in harness, particularly, as in my case, you have to keep on working any way you can to make ends meet.

But it is true that, IMO, B & M experience makes freelancing today easier, and other experiences in many fields also helps - but this is only from the lofty heights of age wisdom.  I am well aware that this opinion is not at all that of someone who is tech savvy and is perfectly comfortable and competent working from home having never had any kind of 9 - 5 work and could probably command a yearly 6-figure salary age 13!  


So in my field (fields) which to start with was in music, and then translation and  publishing (cutting a few decades off  on-the-way here). All this was in tandem with some interim freelance work (before internet), which then somehow developed into my leaving UK and finding myself in arts/crafts and working in an art studio specializing in painted wood  and murals. This was also interspersed with genuine money-earning work with some fairly high-profile people and writers - all to the good, until I finally followed a few get-up-to-date courses and joined - well you know who, as well as hustling for a few outside clients. So a very potted history!


(I think I might redo my LinkedIn profile!)


ETA: Valeria I didn't really answer your question: I try to cut away fluff and streamline my profile to match my offer of translation and editing, which following on from an earlier career in publishing,  I started to concentrate on as a freelancer  quite a few years back. However, in some proposals I have added experience I have had in areas that are not included in my skill-set.




No kidding, it's hard to be optimistic about the whole concept of "retirement" nowadays! 

Thanks for sharing your story and approach! Your profile is mostly focused on proofreading, editing and translation, but it's also interesting to learn about your experience in arts. I see you mention it in the Other Experiences section of your profile. 

~ Valeria
Community Member

Considering how utterly inadequate Upwork has been at filtering out spam posts (there are hundreds right now in the graphic design space alone, every other post is a scam), bringing on people ready to retire who may have more trouble with tech and recognizing a scam might not be the smartest move...

Gina H wrote:

Considering how utterly inadequate Upwork has been at filtering out spam posts (there are hundreds right now in the graphic design space alone, every other post is a scam), bringing on people ready to retire who may have more trouble with tech and recognizing a scam might not be the smartest move...


**Edited for Community Guidelines** More a case of bringing on people who do not read Upwork's rules and regs, who do not look at the help pages, and who have no knowledge of anything at all, let alone acqainting themselves with how freelancing works simply by exploring the internet a bit. Age has nothing to do with it! 




Hi All, 

A few comments have been removed from this thread. I understand that many members are concerned about the topic of Trust & Safety and scam jobs. Our internal teams take it very seriously and have shared information and updates about their work in announcements, blog posts, webinars and on relevant threads. However, that is not the topic of this particular discussion. Please, refrain from posting off-topic comments and making personal attacks. 
Thank you.

~ Valeria

Indeed, age has nothing to do with it. I was under the impression that younger freelancers have grown up being told not to trust strangers on the Internet, but they seem to be just as likely to fall for scams.

Community Member

I am most likely one of the elder freelancers here.  I turned to freelancing around 2012 after I lost my job.  (I had done contract work from 2001-2005 but Hurricane Katrina ended that).  I find that I can earn a comfortable living working about 10 hours a week, so that's wonderful and I make more per hour than most people in my field.  In 1992-1993 I returned to college and got a paralegal certificate.  Prior to that, I had worked in residential real estate, medical non-profits, physician headhunting, retail, and as a background actor for film and TV.  So I bring a wide range of experiences to the platform. I actually mention all of these somewhere in my profile.  One early client hired me because of real estate experience, another hired me because I graduated from college in the same class as his mother, a couple were fascinated with the acting gigs. So I lay it all out and it works pretty well for me so far.

Community Member

After 20 years of working as a designer and creative director, I've been able to use UpWork to transition to a freelance graphic designer and small business owner. In 2020 at the beginning of the pandemic, I started picking up small freelance projects on the side while I was exploring options for the next steps in my career. After a couple of successful projects, it became clear that I could build my own business using UpWork to generate project leads. In 2021, I left my in-house role and am running my own graphic business supporting product-based brands with brand identity and packaging design to grow their sales.

When starting my UpWork profile, it was important to me that I include my corporate roles to show potential clients my real-world expertise. I also referenced these roles in the portfolio examples I added. Looking at it from what potential clients would be focused on, I shared examples and results but left out a lot of detail or skills that didn't apply to their projects.

Hi Kelley, recently I was called for the Talent Scout Group, I had the interview and I felt very sure of my work, I have more than 20 years of experience in graphic design too, a varied experience with all kinds of clients (I have worked as a freelancer for small entrepreneurs as well as for companies like: Diseny, Coca Cola, Philips, so I know perfectly well what it means to handle different types of clients.
I am a TOP RATED designer and I have an Upwork Skill Certification in Graphic Design (none of that changed that my job offers are more consistent and better, there are days that I get 10 offers and then nothing for months) I was hoping that would change with this interview, but they told me that:
"Unfortunately, your skills don't meet the requirements to join at this time."

What kind of skills do you need to be part of a group like this? Despite giving 150% of myself, I do not want Upwork to become a source of income to support me 100%.

A little disappointed that it gives so much to a platform where I don't get consistency and regularity at work by trying so hard.


I was looking the same as you: build my own business using UpWork, but I have to divide between my agency and Upwork because I can grow enought to make Upwork my only income to support myself.

How were you able to get into the Talents Cloud?

Hi Vanina,

I'm sorry that your experience has been disappointing.

As for the Talent Clouds, I applied to the Talent Scout Group when it launched. I was accepted but have not gotten any jobs from the Talent Scout Talent Cloud. The other Talent Cloud I was added to when I accepted a project with an enterprise client. I would try not to take "Unfortunately, your skills don't meet the requirements to join at this time" personally. I think the Talent Cloud has many freelancers in it, but I don't see many projects posted there.


Consider telling your prospective clients in your bio what value you can add to their projects by applying things you learned when working with big-name brand clients. What are the specific lessons learned there that add value to a business of any size? You and I know that as professionals, but clients sometimes need that explained 🙂


As a freelancer and business owner, I agree that relying on one client or one source of leads is risky. 

Community Member

Hi Mark,
I wouldn't say that "going after that generation" is the the right way to describe the purpose of this thread. It's more of a trend we're observing throughout the research and surveys conducted in the past few years and wanted to hear more stories and experiences that may be helpful to others.

I understand your sentiment about private feedback. However, that's not quite related to the topic of this thread.

~ Valeria
Not applicable


I fit perfectly into the category of what you are looking at bringing in, recently retired from my "real career", although I did have almost 18 months of freelance work on Upwork in 2016.

Recently retired I decided to keep myself busy and bring in extra funds, although relatively succesful, I made more than my target for the first 4 months, in fact I made 16 months target.


However, I find the amount of "real"jobs on Upwork is far less than my first stint in 2016, and don't mention the scam jobs,.

And then there is the posted jobs that don't hire, and with the amount of succesful freelancers on Upwork are you really telling me there isn't an ideal candidate in the proposals? as cynical as I am I often wonder if they are Upwork posted jobs to make the platform look busy.

Now lets talk about connects, and before you defend them, it doesn't stop the 50+ job proposals, I see that regualrly, so it's just another Upwork way of creaming more than the 20% off the freelancer.

For me when a company starts to strip away at the resources like that (Freelancers needing to buy connects to stay available)  it tells me the top management have not managed to make their % of growth and the only option is to attack their employees.. It's the start of the slippery slope.

And as the gig economy is going to be growing over the next few years I am concerned that the platforms are not doing their best to attract real clients. Or they woudln't be chipping away at freelancers for connects.


I hope I'm wrong, but the number of people on here voicing the quality and quantity of real jobs sadly may prove to me that I am correct.


Fix the connects, retired folks don't want to pay to start earning, there are other freelancer sites that do that, go on be different.

Weed out scam jobs and please don't tell us to report them, what is the 20% of our fees going to if you can't get that done successfully yourself?

Make clients have payment verified, that will stop the scam jobs or at least some of them,, but I doubt you will do that as you do absolutley nothing to put a block on a client getting onto the platform but make it hard for a freelancer to.


I live in hope.






I couldn't have said it better....

I joined Upwork just 32 days ago.

This is what I accomplished in four weeks: 2 offers, 4 invitations, and the Rising Talent badge which appeared suddenly on my profile on day 27.

So, shouldn't I be "happy"?

Well... no 

The time I invested in this circus is outrageous:

- I spent h-o-u-r-s scanning fake job posts; 

- I had to keep my finger on the "recent" jobs to allow me to identify a match and then submit a proposal early enough to land in the first 5 proposals submitted to the client.  

- I replied very promptly to clients' messages to showcase my responsiveness. But clients couldn't care less what the local time is in the freelancer's time zone when they send their laundry list of questions.

- My proposals were tailored and carefully crafted.  I am sure they were decisive in getting 2 offers.

But, let's get real ..I wrote a total of 28 proposals.

Without having any work history at all,  I suppose this is considered an achievement.

 I can already hear freelancers say this is normal - and why am I complaining?

Well, to each their own... 

The caliber of clients on this platform is mediocre  (I am being polite), and they don't deserve such an investment in time and attention.

I am also appalled by Upwork's complacency with loose and inconsistent monitoring of clients. To me, Upwork is a glorified Craigslist marketplace with an intuitive user interface

So, yes - the 2 contracts I obtained are great, and the clients are collaborative

However, life is short and leaving 20% of my efforts to this platform is not justified.

Once my contracts close, I will close my account to leave this Energy Vampire they call Upwork -







Not applicable

Brigitte, I agree with you completely, I love the energy vampire phrase and it sums it up so eloquently. If I did an internet study of how many times I look at Upwork in a 24-hour period It would be extreme.


I am fortunate, I have a very old client that is still using the platform and I am able to pick up a few jobs each month. If that wasn't the case I would be looking at other platforms such as Fiverr but that is bottom-feeding at best and I would rather not work than be offered $5 for an hours work.


I have started to market directly to non Upwork clients through email, this has had a limited success, will I bring those clients to Upwork? No chance.


The only reason I am still on Upwork was the time I had invested working on bottom-feeder clients to get a good enough JSS to get noticed by the better clients, there are a few out there, saying that my best client is using other platforms as well, as they just can't get the quantity of freelancers to limit themselves to purely Upwork.


I think having a "tag" on your opening statement for proposals is beneficial I use 

"Good morning/afternoon/evening from beautiful Bangkok"

It draws some clients in, some would say it would draw the male clients, but I have found the opposite, the majority of my clients tend to be female.

As for all this hoohaa about your profile showing what you can bring to the clients project, yes depending on the type of contract but the majority of the clients are not going to read every profile to get the job done, why has Upwork created so many different badges and JSS? If the profile was so important then we wouldn't need all these badges would we Upwork?


Oh and those connects, a sign that Upwork is failing to attract quality clients so attack the freelancers to fill the gap in earnings. 


Come on Upwork, make a difference and get your freelancers earning money so that you can too.




Community Member

This is an interesting question. 


I have a pretty varied career history (landscape manager, college professor, currently corporate paralegal) and while I have only just starting using UpWork, I have found that my experience is quite valuable; but maybe not as much as the hobby writing I have done. 


Since all of my writing samples (academic and popular) have been written for hobby ventures or side gigs outside of the scope of my career at the time, I have the odd (but very useful) combination of experience that is not necessarily related to my careers, but is related to my nature. If that isn't leveraging your personality, I don't know what is. 

Community Member

As a textbook GenXer, I bounced around making numerous career changes after graduating university straight into a recession. I was a journalist, tour guide, jewellery designer, theatrical stage manager, and a travel agent - to name a few - with lots of office temp jobs to tide me over when I was "between careers".


One of the temp jobs turned long-term after the company's lead graphic designer took me under his wing and taught me to assist in his department. From there, I took night school courses and studied in my own time until I was able to build up a portfolio and get a full-time job. But the hours were very long - this was on Bay Street in Toronto, Canada's answer to Wall Street - and everyone was expected to work until 9 or 10 at night and often come in on weekends as well. I had no work-life balance. 


My boyfriend at the time was a freelance IT guy. I envied the freedom that he had to set his own hours, and decided to try freelancing myself. I found my first few clients by printing up flyers and going door-to-door to businesses in my neighbourhood, as well as asking friends and family for referrals, until I had enough regular work to quit my job. 


After about two years of this, I met another design freelancer via a networking event, and she mentioned Elance. I signed up in August 2000, when it was still in beta. 


"...how do you choose what to add to your Upwork profile, what to leave out, and what to save for specific proposals?" Like many who first sign up, I didn't choose! I put everything in and signed up to multiple categories, including graphic design, writing, and admin. Elance was crazy at first; like a reverse eBay where there would be a count-down to a job closing and people would place their bids at the last minute, all trying to be the cheapest. It took quite awhile for me to find my feet and figure out what I needed to say instead of tryiing to compete on price. I think that my niche chose me rather than the other way around, because there were just certain types of projects that I could win relatively easily, so I was wasting my time bidding on anything and everything.


I think the hardest thing for me to grasp when I first started online bidding was that jobs weren't going to just to fall into my lap; I had expected that with my experience and skills, clients would flock to me, and it was a shock to realise how much competition I had and how difficult it was to land my first gig. Fortunately, marketing is one of the things that I'd studied at uni, and I did lots of additional research to get tips on how to promote my business. So I'd say that that's my number 1 piece of advice: don't assume that just because you're good at something, you'll be good at freelancing. You need to read, read, read, and learn all aspects of running a business - marketing, bookkeeping, customer service - and realise that building a freelancing business is a marathon, not a sprint.

Community Member

I never worked traditionally. Seriously never!


I don't know what it is like to work from the office, but I have seen people around me leaving at 7-8am to reach the office at 9am and then returning home around 6-7pm. Which seemed to be too much to me since ever. I think I will never be able to do something as such in future. 


My freelancing journey started on social media, where I was vocal among groups with helping people with data science coding practices and using statistical models appropriately, and from there, someone contacted me to hire me as a freelancer and then I found freelancing as a nice career to go ahead with. I don't need to attach myself to labels and continue to work on my academic research at my own pace. 


I found Upwork and created an account, for a month or two there was absolute silence but then I started getting invites to do small jobs. I accepted a few of them and from there my upworking started. I love it, and I feel clients I get from upwork has nice process than those who contact me directly from outside. I hate managing contract and invoicing, as any typical freelancer I do everything alone (yes yes there are many fancy software but they all require quite many efforts and accounting obligations and much time) and using Upwork is just simple, the platform does everything and I feel safe and totally optimistic when starting the work.  


I am planning to take some break from my academic stuff and commit 100% to freelance now and adopting a digital nomad lifestyle soon. It will come a hard way but freelancing is making it possible - pretty sure traditional work style can never make it possible.

I wish you all the success Aru, and I am sure you can do it. But - however boring invoicing and all the other admin stuff is - make sure you put aside a little pot for those unexpected moments like accidents or illness - and yes - retirement eventually! 

Thanks for the wishes Nichola. I hate invoicing and following up with clients and it is the hardest thing when clients are not through Upwork. Anyway, I am yet to start to save on my pace and plan for retirement. Saving comes is always important when one is freelancing, sure. 

Community Member

Its been 1.5 years since I started working on Upwork. I did $1000 worth of work in just $10 to get good reviews in the begining and attracts more client. It was tough but indeed worth it ❤️ I was consistent and worked very hard to get good long term clients. I still remember I found a client who changed my life and I am still working with him & he does not want me to leave him at any cost as we have build an amazing relationship with each other.

I recently quit my corporate job and started as a full time freelancer ❤️ Now, I have a freedom of many things which I cannot event thought of in a corporate job.

Thank you Upwork ❤️ 

Latest Articles
Featured Topics
Learning Paths