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I am trying to look beyond the stereotype, which is as follows: I think of freelancing as a job for a young person, not burdened with family obligations and long-term financial commitments (like a mortgage), who is still far from retirement. It is also a good option to get by when temporarily without work.

I have tried freelancing for a couple of years before my current job found me, and I think of potentially going back to freelancing, since it seems to offer potential for higher earnings. I am however wondering whether it is a good option in a long-term. The reasons are following:

  • Having to freelance while having a family probably makes me less competitive (can't work long hours, can't be available at any time, notably on weekends and during school vacation periods.)
  • Financial stability - slack in the market, change in the habits of clients (I mostly found them via online platforms), difficulty of working intensively in older age (and potentially retiring.)
  • Speaking of age - how would it feel to do freelancing when you are 50 or 60 years old? Do clients even take you seriously?
  • Career development - even if freelancing offers higher earnings, there is probably a limit, due to the time and physical limitations, which is probably reached within a few years. What is next then? - building my own company (i.e., having others work for me)? Positioning myself for a different market segment? Eventually finding a consulting job, affiliated with a big company (i.e., ending freelancing)?

Advice and stories from experienced freelancers would be greatly appreciated.

Similar question: Next level of freelancing and growth

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    Rename the freelancer a consultant and all these pitfalls vanish.
    – user4521
    Mar 12, 2023 at 15:11

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This all depends on how you view what you are doing. If you consider freelancing to be simply being a contract employee (full time employee equivalent), then you are facing the same pitfalls that any technology employee has - age discrimination, need to keep current with technology, etc.

If you consider freelancing to be a business that you are running, then the opportunities and downfalls are different. As you gain experience in business, then the services you offer to your clients can change. You can also sell products and services provided by others. Quite a number of people have built substantial businesses that way - starting as freelancers and building into a larger business. The challenges become things like financing, managing people and projects, finding suppliers, etc. The ebb and flow of business is normal and needs to be planned for.

When viewing what you do as a business, then the sales are different. Sell to the CEO, not to a "hiring manager". At that level, age is an asset.

If you build a business, then one option for retirement is to sell the business.

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  • Thanks, good points! I do agree with what you said about freelancing as an employee vs. running a business. For background: I live in France where permanent employment comes with lots of benefits (in terms of unemployment support, guarantees against being fired, employer-supported health insurance, etc.) , so I have always considered that taking long-term full-time projects as a freelancer is a poor choice - it is like permanent employment, but without the benefits.
    – Roger V.
    Mar 3, 2023 at 15:47
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I think the concept of having to work long hours in order to be competitive is not a valid point. Sure, young single people can work long hours, but it's more about the quality of work and your craftmanship/company branding. Your services and level of quality are the USP. Not the extended time you are willing to work.

As a freelancer, one of the perks (and sometimes pitfall) is that you can set your own hours and time. It's a perk because you know your ability to deliver to your client (quality, deadlines, etc.). When I say it can be a pitfall, I mean that sometimes freelancers work too much and either burn themselves out or the hours worked don't have a positive return on investment.

Personally, I think it's great that you are considering getting back into freelancing. Like you have mentioned, freelancing has it's risks regarding stability. I have always used cold-calling (or emailing) and word-of-mouth, aside from my website (which doesn't normally get me leads/prospects - perhaps I should fix that...), which is a lot of work. In my own experience, I think some of the failure has been around, pricing models and lead/prospect cultivation.

I have friends that use recruiting agencies, and the agencies allow you to either work as a pseudo-employee contracted out by them (they handle your tax paper work and payment) or you work incorporated as a contractor and they are the intermediary that connects you with the client. I would recommend the latter, it gives you more control and they find clients for you.

At this time, I work full-time and work projects on the side (with work/life balance in check), but my goal is ultimately to become a contractor and also produce my own software products.

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There have been many changes throughout the world since the COVID pandemic and not that this is a central theme for my response.

In my region and the regions where my families are dispersed. The lack of an available skilled and qualified workforce are certainly now problematic for many throughout different sectors.

Where previously old age was often seen as detriment to employment. Employers who I speak too and who are dependent upon seasonal and transient workforces, now complain that many younger folk won’t put in the hard yards and even refuse over time or to even complete some tasks.

Options to freelance are now within my region and the many regions both near and far. Freelancing offers a definite advantage to those, who are starting their careers and even older people and retirees who want to return to the workforce.

It’s been interesting watching the socialisation of young and old. It’s been interesting watching younger workers teaching new skills to retirees and retirees teaching a younger workforce valuable & transferable skills, that are still needed in workplaces today.

The passion of respect that I idolise as one of the most important values, are also now complimented with loyalty and honour.

Family businesses looking for loyal employees. Businesses able to negotiate employee relationships from full time, to part time and casual options.

I believe that it’s a workers marketplace at the moment and particularly for freelances and others.

Being able to meet the requirements of a role while bargaining flexibility to create valuable spaces between work family and play.

It’s a good time now to take a chance and challenge obstacles from the past that help people and workers back

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I'm an older freelancer who's been at it for 13 years now as my primary source of income. I have 3 kids and a mortgage. I have no plans to return to traditional employment, though I could ostensibly make more. I agree with that others have said about positioning yourself as a business as opposed to a freelancer. I'm self-employed but see no need to tell my clients that, and I treat my work as a business so they do as well.

Here are my thoughts:

  1. The inherent flexibility of freelancing is more of a draw than deterrent for me, as a mother of 3. While I don't have to work late or weekends, I can if I need to. It's about managing client expectations and setting boundaries and schedules for both work and your personal life.
  2. There are ways to secure regular income aside from hourly work, such as offering various services on retainer or other passive income opportunities. For example, I offer website hosting to my clients which requires little additional work on my end. Depending on your industry, you could create an e-learning course and sell that. Freelancers should have 3-6 months of expenses tucked away in savings for those rainy days and downturns. (I'm still working on this).
  3. As an older freelancer who's met and worked with fellow older freelancers, clients take you as seriously as you take yourself. Use the term "solopreneur" instead of freelancer, for example.
  4. How much does career development matter if your career is you? I've grown my "team," meaning hired other contractors, to help meet my clients' needs. That can increase my income as well. And of course, keep raising your rates until you're comfortable.
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I've been freelancing for 20+ years. Probably not in the same direct field however.

  • I never want to hire employees.
  • I detest having to subcontract work and prefer to do it myself.
  • I never want to build a "company/studio".
  • I never want to work more than 30-40 hrs per week. However, if there's a plethora of work, I have been known to in order to keep clients happy. Most often, I put in 20-30hrs a week tops.

Everything you want is possible via freelancing. I'm not implying it is always easy, but it is possible.

Everything is dependent upon building a stable, reliable, and repetitive client base.

Finding good clients who constantly need more work can take some time (and luck). However, once you reach that plateau, things rarely tend to drop again. I avoid contract work.. I am free to work for anyone at any time and no single client has any contractually committed portion of my time. I also avoid the "one-and-done" clients. I want clients with continuing needs who are as vested in remaining current and updating projects as they are in the inception of projects.


That being posted, 2022 was a struggle... after the pandemic many clients were in "recovery mode". While I had no issues during the pandemic, the year afterwards was probably my toughest year to date. But now, in 2023, things are ramping back up to normal, steady streams of income.

One just has to prepare for lean times rather than "spending the paycheck" as soon as you get it. I have a mortgage and commitments.. I haven't been considered "young" for some time. :)

I'd wager that much of the struggle today would be the pandemic recovery many business find themselves facing. The pandemic actually taught many smaller companies that they could hire in-house staff - which merely works remotely. So.. client acquisition is a bit tougher today than it was 3 years ago. But the clients are out there.

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  • Thanks. What you said about client base gives food for thought.
    – Roger V.
    Mar 15, 2023 at 19:59

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