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  • Writer's pictureJeanne and James Bellew

Is Freelancing Right for Me? Essential Questions to Consider

Updated: Jul 3, 2023

Have you ever found yourself daydreaming about a different way of working? Perhaps you…

  • Yearn for more freedom and flexibility,

  • Want the ability to chart your course,

  • Need some income without getting a traditional job

  • Desire to be self-employed without heavy upfront capital

  • Want to keep busy, stay engaged, use your skill set, and help others

We daydreamed about all the above. After a career fitting into "the box" and working through such challenging global events as September 11, the 2008-2009 recession and its aftermath, and the pandemic, we decided it was time to move forward and try something new. When we finally determined that moving abroad was our next step in 2021, we had to figure out how to make money.

We weren't ready to retire for two reasons:

  1. We still needed an income, while not as much as we used to, and

  2. We both like to stay involved with others, to be of service, and use our skillset. Staying active and engaged is essential to (all of) us as we age.

Our goal? To earn money where and when we wanted while living in Costa Rica and traveling. Do you have a goal?

What Are Essential Questions To Consider?

So, before we leaped, we had to consider some thought-provoking questions to determine if working online (we didn't even use the term "freelancing" at the time) was right for us.

Here are some key questions we asked ourselves to start calibrating if working online would help us move forward. I've added some of our true answers in italics. Hard truths…

What thoughts come up for you when asking yourselves these questions?

What feelings dominate me the most?

  • Frustration, despair, and overwhelm

  • Apathy - unmotivated by our jobs and life

What keeps me awake at night?

  • Overwhelmed and confused about the future

  • The thought of getting up and going to jobs for a lifestyle we didn't care about, i.e., mortgage payment, property taxes, buying stuff, etc.

  • Getting sick and being bankrupted due to healthcare bills

What makes me most afraid?

  • Becoming stuck with no way out

  • Not having enough money to last through retirement years

  • Getting sick and being bankrupted due to healthcare bills

What makes me angry?

  • Trusting people with our future that maybe we shouldn't

  • Complaining and whining all the time and taking no new action

What are my top daily frustrations?

  • Making enough money to live but not enough to save, see family, and travel

  • Working long hours and not getting ahead to live the life we want

What makes me happy?

  • Good health, traveling, working the way we want, contributing to others.

What is a good life for me?

  • Staying in good health, traveling, working the way we want, and contributing to others (there's a theme here 😉)

It became clear that our life wasn't best for us, and we wanted our "good life."

Important Insights

Besides the above questions, we've also learned that there are important insights (seeing into inner character or underlying truth) about yourself when determining a freelancing life. How do you answer these questions?

  • Do you have a positive attitude?

  • Are you future-focused?

  • Are you a life-long learner?

  • Do you practice optimism?

  • Are you resilient? THIS IS A BIG ONE

Do you have the attributes (quality, characteristic, character) to be a successful freelancer?

  • Can you work independently?

  • Are you self-directed and flexible?

  • Do you have good time management skills?

  • Are you able to meet deadlines?

And finally…

  • Have you accumulated skills and knowledge over your lifetime and career?

  • Are you computer literate? (You don't have to be techy)

  • Do you have access to the Internet?

  • Is your mindset the right one? Do you practice optimism, gratitude, and courage?

  • Are you open to continuous learning and adapting to changes?

  • Are you willing to invest time and effort to build your freelance skills?

The above is a starting point for self-reflection and evaluation.

While freelancing offers freedom, flexibility, and the potential for a fulfilling career, it's essential to consider your skills, mindset, and goals. (As coaches, we help here 😊)

Take a deep breath, be honest, and evaluate whether freelancing suits you. If you're not sure, we understand. (As coaches, we help here also. We can chat 😊)

Don't let fear hold you back—embrace the possibility of freelancing. It's the future that allows people to work as part of the "independent talent economy" and are no longer tied to one employer, one office, or one client. In addition, it gives new freedom to baby boomers whose predecessors didn't have the opportunity to continue using their skills and making money after the "acceptable" age of retirement. It's an amazing time. Freelancers are thriving.

Pura Vida!


Jeanne and James

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