ask A.

Common sense advice for life and work by A. from recognizd

What should I choose between financial security and a sense of freedom?

Dear A.,

What should I choose between financial security and a sense of freedom?

— You Say You Want Your Freedom

Dear You Say You Want Your Freedom,

We’re in the question business here at recognizd, and binary choices are kind of our thing. Doing the dishes or playing DJ at a party? Coffee or tea? Solo getaway or all-out celebration? 

So, your question should be right in our wheelhouse. 

When I was much younger I’d have answered without hesitating and said, if you have to choose, choose freedom. Indeed, in my own life I’ve often chosen in this way. Jumping on a plane to France at age 19 not knowing a word of French or anybody in Paris. Walking away from an on-paper excellent marriage. Leaving the tech industry for brick-and-mortar retail. 

And yet… freedom and security aren’t mutually exclusive, nor are they opposites, in fact they’re pretty interdependent. 

First of all let’s get real about why we work: we work to afford our lives.

If we are somewhat lucky, that work isn’t too horrible. If we’re very lucky, that work is fulfilling and rewarding and specifically energizing to us. But, that’s rare. 

And so, tradeoffs are made. Maybe this job is better paid but has worse hours. Maybe that job is in an industry we want to learn more about but it requires commuting. Maybe there’s a new baby at home and we need a job that allows us to be good at both.

In an absolute sense, anything that makes you feel small, or stuck or confined is not a good place to stay for very long, and you might also enjoy reading this letter.

Everyone talks about work-life balance and I’m sorry to say that I personally think that it’s kind of BS. We have a life, and work will be a large part of our waking hours for most of our best years - seeking an equitable balance seems optimistic. But, movement can be measured in inches. A slightly better job is worth going after, as is a slightly higher salary. Both will move you towards your goals of being free and also secure. 

I have worked entirely for myself for the past one and a half years (I own a wine store). Whilst I am my own boss and technically I call all the shots, in reality I’m now answerable to perhaps the most ruthless master of all: my customers, closely followed by my bank. I also have to be physically present at my “office” 5 days a week, rain, hail or shine (or when I have debilitating endometriosis pain). With these factors, I’d give my current job a freedom rating of about 6 out of 10 and a financial security rating of probably a 2 out of 10.

Previously, in my former job, I could work pretty much from anywhere with a wifi connection, what I worked on day to day was largely decided by me (aligned with the company goals), and salaries in the tech boom were more than solid. Let’s say an 8 out of 10 for freedom and a 9 out of 10 for financial security. 

The years of working in a more financially secure job opened up the opportunity to spend the past few years in a different season of life, where slowing down, creating community, a brand people love, a safe physical space for people to meet and learn could be placed above both personal freedom and financial security. Balance for me came over a 5 year period. 

I have a good friend who works freelance extremely intensely for 9 months of the year and spends the other 3 visiting her family on the other side of the world. Another friend is in a job that he doesn’t particularly love, but that more or less lets him do regular 9-5 hours and still train daily for sport competitions. It looks a little different for everyone. 

So, perhaps it’s most helpful to start with asking yourself, which season are you in?

— A.