Will you really be happier working for yourself?

Will you really be happier working for yourself?



Three years ago, I had a dream (which, admittedly, was a lot more modest than Martin Luther King’s): to spend my days, at home, in my pjs.

Happily, this dream aligned rather nicely with a few other dreams I had: to work with like-minded entrepreneurial souls and to create something I felt was truly meaningful.

And so in January 2013, fresh from a ‘no need to return in the New Year, we’re good’ text from my former boss,  I made the decision to venture out on my own. Immediately, I transformed my freelance writing business into a fully fledged communications and copywriting agency. A few months later, Happiness + Wellbeing Magazine was born.

All systems were go. Dreams had officially taken flight.

And while I’ve outgrown the whole pjs-is-my-uniform stage, I’m proud to reveal that those dreams are still flying (I’m frantically flapping after them, red-faced and crazy-eyed).

But did working for myself make me happier?

And why was I proud? Why not happy? Content? Blissed-up, blissed-out or even over the moon?

Well – and this brings me to the point of my article today – because working for myself turned out to be a mixed blessing. (Read my other article, ‘13 things I swapped when I started working for myself‘ to find out more.)

And while I’m definitely happy – and happier – than I was a few year’s ago, it was actually just as important for me to be proud of myself as it was for me to be happy (and happier).


You see, in essence, I swapped a lot of my pre-working-for-myself problems for a fresh batch of working-for-myself problems. They weren’t worse, or better, than my old problems. They were just different. But they were still problems, or to be more positive, let’s call them ‘challenges’. They were still challenges.

However, what we often forget is that we don’t usually hate absolutely everything about our current job or situation. And in hindsight, there are even things we may appreciate. For me, I liked my co-workers and enjoyed being around people. Working for myself, I miss the people – and the stable income – but have chalked up a new batch of positives (like flexible working hours, being able to work from wherever I want and choosing to only collaborate with clients I adore).

Which ties in with my message for you:

Only you can make you happy.

Sure, by quitting your job and starting your own business, you may become happier. But it’s not a magic elixir for eternal happiness. The short-term exhilaration will fade, leaving space for new challenges to creep in.

Because no external situation, whether it be your occupation, your partner, your wealth or your location, can make you happy forever.

Happiness, as I have learned firsthand, is both a conscious decision and an active journey. Only by adventuring into my inner world (by transforming my negative beliefs and reclaiming my self-worth) was I able to dramatically improve my outer world.

BUT, that doesn’t mean you shouldn’t chase your dreams. It may very well be part of your personal happiness journey.

Instead, focus on aligning with your unique truth, passions and journey (to greater align your inner world with your outer world) and understand that you’re not swapping the job from hell for a Utopianesque professional world with rainbow unicorns and peachy cherubs.

You’re swapping challenges for challenges. Triumphs for triumphs. Positives for positives.

Because we’re not playing in a perfect world. And there will always be challenges thrown in our path, irrespective of what path that is.

And so my advice to you is this: treat your career the same way you would your soulmate. Know what you want – and need – from the relationship. Accept only the best for yourself. Choose wisely. And then commit yourself to making that relationship work, through rain, hail and shine.

Read more business articles on my copywriting site, Wild Spirit Copywriting (

Cassandra Lane

Cassandra Lane is the happy founder of Happy + Well Academy and the Editor-in-Chief of Happiness + Wellbeing Magazine.

Cass also owns and runs Wild Spirit Co., a creative copywriting (which is just fancy word for ‘writing’) agency devoted to helping soulful small businesses, entrepreneurs and start-ups communicate their brand with confidence. You can hire her for website copywriting, eBook copywriting and editing, sales page copywriting, article writing, blogging, editing, proofreading and more. Visit her site at

A quintessential daydreamer with a penchant for cloud-watching, reading, yoga, hula-hooping and crisp, mountain air (or really, nature of any kind, but mountain air sounded way cooler), she can usually be found with a book in one hand and a journal in the other. The pen, of course, will be tucked behind her ear at some stage and quickly forgotten as she floats through the rest of her day.

Latest posts by Cassandra Lane (see all)


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