Freelancing Should Never Feel Off Limits

Freelancing is a Lifestyle Choice

Freelancing isn’t for everyone, but it should be an option for everyone. Working from home, your local coffee shop, or co-working space, fitting work around being a stay at home parent or carer, or managing your career on your terms. Whatever your reason for working non-traditional hours, you’ve chosen a lifestyle where you fit your work around your life; not your life around your work.

More and more people are turning to freelancing, preferring the flexibility it allows them to meet both their career and life goals. In terms of career, freelancing gives you the freedom to work on the projects and types of work that excite and delight you. Naturally, you still must perform the administrative functions of managing your business outside of your client work. But, the control and ownership you gain from knowing those arduous tasks are moving you towards more of the work you love makes those jobs much easier to take on. Freelancing also gives you the freedom to work when and where you want to. In reality, that may mean working weekends or late evenings to finish a project, or getting up early in the mornings to squeeze a couple of hours in before your kids get up.

Either way, freelancing gives you the freedom to manage your life the way you want to. You can skip the traditional 9-5.30 routine and long commutes in heavy traffic, and you can banish rushing home to catch a glimpse of your children before they fall asleep.

But, it isn’t the Easy Option

Freelancing is a personal choice, and it can be hugely liberating. But, it can also be lonely, draining, daunting, and overwhelming, not to mention a huge burden on your financial resources. Managing your working life and career alone is incredibly challenging. Time management and self-motivation are two of the biggest hurdles but, here in the US, managing your benefits as a freelancer is often the main obstacle.

As a freelancer in the US, you are not entitled to benefits. You can build your benefits package yourself but, having moved from the UK to the US and feeling the pain of having to file my own taxes every year (freelance or not,) I can imagine this wouldn’t be a walk in the park. Never mind navigating maternity or paternity benefits. I wrote about this back in 2018 after having my first child.

Freelancers Need Benefits to Survive

For these reasons, I was delighted to hear discussions of ways to support freelancers on a favorite podcast of mine, Hello Monday, hosted by Jesse Hempel from LinkedIn. On ‘Hello Monday,’ Jesse and her guests discuss ‘how the world of work is changing, and how that work is changing us.’ In her latest episode, she was talking to a fellow freelancer about her concerns of continuing to freelance after turning age 27, and no longer being able to feature on her parent’s health insurance policy.

She felt that having to cover the extortionate cost of health insurance on a freelancer salary, despite loving her work and flexible lifestyle, wasn’t feasible. This made me sad. Being unable to manage a freelancer life because you can’t find the work or you don’t make enough money to manage everyday costs is something freelancers have to learn to figure out. But, being pushed from the freelance world, due to insane healthcare costs, is a travesty. The freelancer’s example of the expenses she was expecting to encounter, was upwards of $800 more per month just to survive with benefits. Of course, this figure is relative depending on the state you live in but, either way, that’s a very high fee if you’re earning an average wage.

Finally, Help is at Hand

Sarah Horowitz, from the freelancers union, was talking about a new private service set up to support freelancers to manage their benefits. It’s designed to help freelancers to find the best health insurance and pension deals available to them. I imagine the service works much like when you use a website to find your best car insurance deal. They do the hard leg work to find you the best provider, plus they partner with providers so they can engineer better deals on your behalf. To do this, they charge you a monthly fee.

This service is called Trupo, and is a startup founded about a year ago. Unfortunately, it’s currently only available in New York state. Given the rules and regulations are vastly different from state to state in the US, this doesn’t surprise me. It’ll take time to expand such a service. New York is also one of the more progressive states, so it may be difficult to shift mindsets to develop services that support freelancers in other states.

The Fight Isn’t Over – We Need to do More to Support Freelancers

Although this service is a fantastic start, and much needed, the question asked on the show was, will the government follow suit and offer state-funded benefits for freelancers? My thought is, not any time soon. Hopefully, they will see the need, but if it’s anything like maternity leave and pay, I’m not convinced.

There are numerous advocates out there driving the need for flexible working lives – Anna Whitehouse or Mother Pukka, is one such example in the UK. I’d love to see more of these advocates, especially in the US.

As an expat, knowing and living life one way in the UK for much of my life, it’s incredible to move somewhere new and to see how other people live. The impact of societal structures on employee, and life engagement seem much more glaring to me as a outsider. In my view, we need to be doing more to encourage flexible working opportunities for people who want or need them. We need to try to shift thinking and processes to allow people to live lives that support human nature, not fight our ability to be human.

Employee Engagement and Experience, Lifestyle Engagement and Experience




Freelancing Should Never Feel Off Limits

  1. Beraaz Italia says:

    Hi Rebecca Longman
    How do we start or scout for free lancing opportunities. I am a HR professional based out of India .

    • Alexa Bennett says:

      Hi Beraaz,

      I began by cold emailing consulting firms that I felt offered programs related to my skill set. I built my network from there. My work is now a mixture of freelancing, consulting services, and building my creative offering to grow my business. It takes work and persistence, but it pays off in the end. Good luck!

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