Making The Leap From Legitimate Job To Passion


Last summer I was working on a feature for Tobias magazine about the bestselling book The Happiness Project, the fruit of author Gretchen Rubin’s desire to find greater happiness in the daily circumstances of her life.

Part of Rubin’s struggle was finding happiness in her work, something all of us wrestle with. And one sentence she wrote hit me like a ton of bricks, as Rubin grappled with her decision to leave law and become a writer. It was a comment she made to her sister one night on the phone.

“I worry about feeling legitimate. Working in something like law or finance or politics would make me feel legitimate.”

Why did I find this so striking? Because I had the same fears — not just about legitimacy, but right down to defining them in terms of law, politics and finance. A portion of the journal I kept even spelled this out to a tee.

The question of legitimacy is really about fitting into the world around of us. It’s not unique to law, politics and finance and certainly not unique to Gretchen and me.

Heck, it’s even a key subplot of The Godfather trilogy, the story of the Corleone mafia family. (“You have my word, Kay: In five years, the Corleone Family will be completely legitimate.”) If even mythical figures in organized crime want legitimacy, can the regular person be blamed for having such fears?

We can’t be blamed for our cravings, but we do need to ask ourselves if they are…well, legitimate. If one has a natural talent for something should we not develop it, and more than just on the side, while we do a “real job?”

When I interviewed Gretchen she told me “the urge to write became irresistible. I had an idea for a book. I was already writing it on the weekends…I couldn’t think of any legal job that I wanted and I decided that I had to take that leap.”

Gretchen found her confidence, in part from her sister, who was unapologetic in her love of teen fiction and had gone on to a successful career in commercial television. Her sister reminded Rubin that she’d always had the desire for legitimacy and would have it forever. Since going to law school and clerking on the Supreme Court hadn’t filled that craving, she pointed out, it was unlikely anything ever would. Simply accepting that Gretchen struggled with legitimacy cravings but would not let them determine her next step made the difference for her.


Buried talents

The advice Gretchen received from her sister has its roots in the Gospel, in the Parable of the Talents (Mt 25: 14-30). The master of the house summons three servants and gives them “talents” to use in his absence. The first two make use of them, grow them and are rewarded. The third servant buried his talent in the ground for fear of losing it and was cast out. The other two, because they had been faithful in small things, were given bigger opportunities.

Reading the Gospel is always inspiring, but bringing these passages to practical effect is where the struggle lies. A recent forum thread here on CatholicMatch saw “Faith Hope & Love” editor Christina Ries ask members what their dream job was and what they were doing to get there.

As I read through the responses, I was struck by how many people dream of doing creative work. When one contrasts the creative desires that exists with the barrenness of most popular culture, it suggests a lot of buried talents sitting out there.

So where does that leave us?

Gretchen was living in a position of financial security and, thus, able to take a risk. Most of us do have to be concerned about our short-term finances, and I’m not suggesting everyone go quit their jobs to become artists on the grounds that it’s what the Gospel told them to do.

What we can do is dig deeper into the meaning of this parable. The fact that the productive servants were given larger tasks to do as a reward suggests that we should start small. Be faithful to one particular venture and see where it goes.

In the beginning this does mean doing our dream on the side while working a “legitimate job,” but we have a different orientation than the world. A legitimacy craver sees that as an end point. We see it as a beginning point. They see it as a hobby, expendable if time constraints become too much. We see it as a responsibility — one that may not pay the bills yet, or even generate much revenue at all but will in time as we follow the path our talents take us.

The desire for legitimacy will always be powerful, because it combines the pull of the world — whether it’s the desire for money, prestige, to be pleasing to family and friends — with our own short-term fears. Face it, most “legitimate” activities pay better than our dreams do, at least at first.

Put those two together and you have a worldly force that can bury you. In the end, the path is really as simple as the advice Gretchen took from her sister: ignore that fear. Be who you are. Not easy, but simple.


Slow and steady

For me, my own path of being a writer has followed a slow progression but one marked by growth. I used to work as a courier at a law firm.

Back in 2003-05 I created a website where I just talked about all my interests, from faith to politics to culture to sports.

As enjoyable as that was, I eventually realized that I had to narrow it down, so I focused on politics and sports and created three blogs that reflected my interests and beliefs. I also wrote and self published an Irish Catholic novel.

Finally, in 2009 I decided to focus on being a sportswriter.

The legitimacy cravings are still there — “You aren’t making a difference” is the most common one, with the temptation to return to political blogging, in spite of the fact that I often burn out on politics.

Writing about sports brings me happiness, and my new exclusive focus has led to some arrangements for greater exposure, a radio podcast and, so far, a little bit of spending money. It’s not where I want to be, and the pace is slow and frustrating. But it’s further along the journey than when I started.

I can look back and see how much how I’ve been slowed down by getting sidetracked by “legitimate pursuits.” Ironically, in following the advice of the legitimate world, we probably cost ourselves more time — and yes, money — than we would by just staying focused on what we love the most.

I don’t know where the Road of the Talents ultimately leads. But I hope to see you traveling down it with me.



Editor’s note

Get inspired by fellow CatholicMatch members planning to leapfrog from day job to dream job.



  1. Hank-539713 February 5, 2012 Reply

    Thumbs down.
    This author does not get how most people’s skill and education do not translate into getting a job, much less a dream job. Don’t forget about circumstanses beyond our control. No matter how much he wants the job, a deaf-mute will never be hired as a radio announcer. A Jewish woman can not join the Knights of Columbus. The cronic unemployed have it really bad. I have a brother-in-law with a degree and 10 years experience as a mechanical engineer, who has worked the last 18 years of his employment as an IT Systems Annalist. He has not been able to find work for the past 5 years. I spent 6 semesters going to night school to get my MBA. In the past 7 years the only job offer I have gotten is to sell life insurance. No offence to the sales profession, but I am not a any kind of a salesman, nor care to be. I have a brother and a dozen skilled and educated friends out of work with no prostpects in sight. And don’t even tell me about moving geographicly. Early in my career I moved four times to pursue that better looking position. Each job turned out to be worse than the one I left. I was fired from two of them, not because I did anything wrong, but because we were a bad fit for each other. I once had a job that was so bad, they fired me because I conplained,,,that my paycheck bounced.
    The bottom line is — IT IS TOUCH OUT THERE. I don’t need an out of touch with reality, “pie in the sky” writer telling me about dream jobs that do not exist. That Country singer is correct — life sucks and then you die.

  2. Sherrill-anne-13557 June 3, 2011 Reply

    This reminds me of a friend whose daughter left her job to do paintings.Her husband was very supportive taking care of the children while she painted.He eventually left his cushy job to assist her with the marketing of her paintings.Today they have been richly rewarded for the decision they both took.

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