Risking All To Gain All: It Was Time To Take A Leap


This past June I wrote a post for Faith, Hope & Love reflecting on the struggles one faces to try and utilize our God-given talents. As part of my reading of Gretchen Rubin’s best-selling book, The Happiness Project, and subsequent interview with the author, I had come to the conclusion that it’s the quest for a worldly sense of legitimacy, combined with very real concerns about financial security, that often keep those of us who want to use creative talents held back.

In November I took the final steps toward making my own goals and hopes a reality. I left my full-time job in order to focus on writing full-time. I’d like to share with you some of the reasons I concluded the time was ripe for such a move and the struggles I am currently dealing with in the embryonic stage of this project.

I’ve been in the workforce for nearly 20 years now, and while one should never say they’ve learned all they can, I do believe that anything I could learn at this point can’t make it worth the lost time in starting my own business. At age 41, I’m roughly the same age my father was when he took the entrepreneurial route, one that would enjoy lasting success.

Furthermore, my current state in life makes taking a risk feasible. I’m not faced with a large mortgage payment, my car payment is modest, I don’t have consumer debt nor any children to support. In the course of my life, I’ve accumulated very little in the way of financial assets (well, almost nothing to be frank).

But through a concerted effort not to carry consumer debt, I was able to put together a strong credit rating, which could be cashed in to obtain access to additional funds for start-up. Sometimes what you don’t have is as valuable as what you do, and in this case, clean credit doesn’t look flashy, but it has value all its own.

I weighed these considerations — timing and financial obligations are factors everyone shares equally —  but I had a third prong in the equation that also pushed me toward a move. My full-time job often required that I do things that violated a sensible Catholic code of ethics and there was no getting around it. My job required a daily balancing act: to refuse to do the work would be to take my employer’s money without providing the labor.

To do the work would be to do things I was quite convinced were wrong. After three-plus years of daily agonizing, constant struggles of conscience leading to physical breakdowns, enough was enough. If risking this job was all I had to in order to take a shot at my dreams, then it was time to go for it.


Calling it quits

On Nov. 17 I walked out the door of the office for the last time and into the world of self-employment. The first challenge I’ve faced is the temptation to try and twist this new work into a 9-to-5 job all its own — a so-called “legitimate” job. I find myself already comparing the time spent on work for my new project with that I did as a full-time W-2 employee. The problem is, those comparisons don’t work.

The first key difference is that the business I’ve chosen is sports writing, and in any sort of entertainment field, one has to remember that your audience is coming to you at times that are necessarily outside the scope of a 9-to-5 day, which in turn means you have to be prepared to be planted and on the job at those times. The other side is this: As an employee you could reach the end of the day, and if things weren’t coming together, you ultimately have the luxury of saying “to heck with it, someone else can worry how to bring all this work together to drive revenue.”

Now I’m the person who has to figure all that out. It’ s nothing I didn’t expect or welcome, but it immediately gives one a different outlook.

Perhaps the biggest challenge of all is that of not allowing worry over the big picture to drag you down. I’ve been on this project full-time for less than two weeks, and not a day goes by that I don’t  fret about several aspects of the project. And it’s necessary to step back and evaluate the big picture, determining where problems lie. The challenge is not letting the worry cost you any mental energy or focus from the daily tasks.

Football coaches at this time of year are constantly telling their players not to worry about the big picture of making the playoffs or a bowl game. Just block or tackle the man in front of you. It’s easier said than done, but it simply must be done.

Ultimately the struggle above boils down to having faith, the faith that God will oversee this project and bring it to a successful fruition, and that if nothing else, even failure won’t be a disaster but a learning experience. As I debated the merits of making the jump, I found myself wanting to wait for a situation when security was complete.

Waiting for security to be complete is tantamount to saying one will never start. It may sound silly, but I often think of a scene in the 2003 caper movie Oceans 11, the George Clooney/Brad Pitt/Matt Damon remake of the Frank Sinatra classic. Two characters, Linus Caldwell and Danny Ocean, are getting ready to launch themselves about 60 feet into vault, with rope having to hold them up at the end of the jump.

Caldwell looks at Ocean and asks if the rope is going to hold.

The reply is simple: “It should.”

It’s a nothing line in the course of the overall movie, but it conveyed a clear reality that the rope might crack and they’d crash on the floor. But the percentages weighed heavily in their favor. If they waited for a perfect guarantee, they’d never crash, but they’d never get at the $160 million in the vault.

If the percentages in your favor, it means making the leap meets the test of the Catholic virtue of prudence. This is entirely different than saying it’s a lock to work. But it the time has come. That’s the spot I was in and why I was glad to walk out of the office for the last time 12 days ago.


Editor’s note

Dan Flaherty’s website, www.thesportsnotebook.com, is due for full-scale launch in mid-December, in time for the college bowls and NFL playoffs. Better mark that page now! And in the meantime, leave a comment to share your insights on self employment.



  1. Mary-25961 December 12, 2011 Reply

    Dan, I am happy to hear about your on your decision and will pray for your success. Remember if we don’t let go of the limb we can’t be saved 😉 God’s blessings and good fortune

  2. Nancy-632072 December 11, 2011 Reply

    Good for you – I pray everything works out for you – there will be struggles I am sure but you get to be in charge and with God’s help you will do great – most of all have fun and enjoy the ride –

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