Caution to the Winds
Life in Pencil is joined by another guest blogger! Today we’re treated to the Life in Pencil musings of Anne’s sister, Gale. Anne and Gale have shared, as you might imagine, their entire lives together. They are distinct in many ways, but they share some mutual loves: a well-planned life, a good list, and good writing. And like Anne, Gale is also drawn to creative people, projects, and ideas. Enjoy her thoughts on living a Life in Pencil.
Posted by Gale
- In 1984 a young criminal defense attorney was inspired to abandon his career in the law and take up work as a novelist.
- In 1978 an energy policy writer in the White House left Washington to buy and run a specialty food store on Long Island.
- In 2004 a young graduate student dropped out of her PhD program in cultural anthropology to start a food blog.
What do these people have in common? Well, for starters, you may have heard of John Grisham, Ina Garten, and Molly Wizenberg. Also, they each took big risks to pursue their passions, and each found success in doing so. And lastly, collectively, they raise a frightening question for me:
Do I have to throw caution to the winds in order to follow my bliss?
This is scary because I don’t know whether I want the answer to be Yes or No. As it is, I live a pretty conventional life. I live in a medium-sized house in a suburb of a big-ish Midwestern city with my husband and son. I have a full-time job in a nondescript office building. I have two dogs. And I have ordinary hobbies – cooking, reading, exercise. As you can see, it’s all pretty, well, normal. And when I type it out like that, it almost sounds boring. But here’s the kicker… I’m really happy.
And this is why people like John, Ina, and Molly get me scratching my head. They make me wonder what that says about me. Am I a person who just happens to be best-suited to a conventional life? Or am I being a complete and utter weenie; faux-claiming happiness when I truly long for something bigger? And further, if my happiness in life is genuine (it is), then does that mean that I’m painfully bland and uninteresting?
Don’t get me wrong, there are some interesting things about me. I’m mostly fluent in Spanish. I’m a talented equestrian. And I can sing. Yet none of these things is an active part of my life today. Worse still, each used to be, and was at some point left behind in deference to something embarrassing like convenience or fear. At 15 I quit riding horses competitively because I was afraid of having high school memories devoid of things like homecoming football games and prom.

That could be me 20 years ago. Sometimes I really miss those days.
After graduating college with majors in business and Spanish, I didn’t pursue a job that used my Spanish because I was afraid my language skills weren’t polished enough. And after spending my entire life singing in church and school choirs and doing sporadic solo performances, I’ve rarely sung anything but a church hymn in nearly ten years and I have no idea why.
As with anything, there are matters of pragmatism to consider. I get paid a lot more as a marketing professional than I would in a career as a horseback riding instructor. Also, I love my family, and I would miss the bejeezus out of them if I high-tailed off in pursuit of some fancy-pants dream. And that pesky thing I mentioned before… my life as it is makes me happy.
Let’s stop and consider that life:
I would be grossly remiss to overlook the significance of having a satisfying career. I really love my job and I have a good head for business. My career may not have required me to “risk it all” to get where I am, nor has it provided me with fame or incredible fortune. But I enjoy what I do and I’m paid well for it. And that’s not necessarily an easy combination of things to find.
Also, I do have hobbies that I actively pursue and enjoy (Spanish, horses, and singing notwithstanding). I love to cook and I try to cook one new thing each week. I also love to entertain and we regularly have card parties and dinner parties, in addition to one big bash each Christmas. I read interesting and challenging books. And we are frequent travelers to interesting places.
So as for this whole Life in Pencil thing… why is my current life not enough? Or, better yet, if I’m happy and satisfied, why would I even consider that it isn’t?

How could I ever want anything else?
What exactly is it that I’m seeking that I don’t already have? And how might my life better off if I abandoned it for something riskier and more grandiose? Maybe it wouldn’t. Maybe I have my bliss right here. Maybe, for me, Life in Pencil means rolling with the here and now, and not worrying about bigger or better. Fame and fortune be damned. I’m picking the life I have.
What about you? Do you wish you were more daring? Or are you happy where you are?








September 16th, 2009 at 7:02 am
Gale, these are tough questions that I’ve pondered myself. The best answer I’ve come up with is that we all have different levels of comfortableness with risk taking, and we all have different things that make us happy. There is a great book you might enjoy by Harvard psychologist Daniel Gilbert called “Stumbling on Happiness.” He has studied happiness his entire career, and looked at some of the questions you pose.
September 16th, 2009 at 9:11 am
Ultimately, you have to decide if you are living your life for yourself and your family, and the happiness it brings you, or, are you living your life for the critique of others.
At 60, I frequently reflect on what I might have done, but chose not to do. In the end, I almost always land on this spot: If anything I might have done (travelling more in business, taking larger entrepreneurial risks, moving to a larger, more competitive city, etc.) would have, in any way, changed the way my life has turned out, or the family times I have had, or the friends I have, I wouldn’t make the trade. Yes, I do challenge myself that I haven’t changed the face of the world (or even my home town), but in the end I am mostly content. And contentedness does mean merely “settling” for mediocrity. It just means you can appreciate the life you have been given without the burden of over-analysis or beating yourself up for a long list of shortcomings.
September 16th, 2009 at 9:54 am
Well said, Gale. Is it a bad thing to be content without accomplishing big, glorious things? Is that settling? Wouldn’t many people be better off if they were fulfilled by the ordinary? Congrats to you for finding what we’re all seeking – happiness!
Maybe the “life in pencil” part comes in knowing that today’s path to happiness does not equal the path 10 or 20 years from now. The path will be erased and redrawn many times. As much as we try to control it, nothing is permanent. Be ready for the next fork in the road and enjoy the smooth, happy sailing while it’s here.
September 16th, 2009 at 11:59 am
Wonderfully written, evocative post. As you know, I contemplate happiness almost on a daily basis. What is it? Is it different for each of us? Can it be taught or learned or simply stumbled upon. I don’t pretend to know the answer to any of these questions. But I do think they are worth asking. And here you are asking such questions, bravely, eloquently.
I do not think there is anything at all wrong with deciding that you love the life you live. But I also think that you can live that life and soak up its rays while contemplating questions about evolution and meaning. I think as humans we are wired to reach beyond the periphery of our own bliss and ponder what else it is that we might want or hope for. I don’t think this reaching or pondering itself is evidence of inchoate dissatisfaction necessarily, just of the fact that we are human.
From what I gather, you have a rich and meaningful life, but that doesn’t mean you need to stop dreaming, right?
September 16th, 2009 at 2:43 pm
There are days that I am happy where I am, I couldn’t imagine a better life. I have my house, my wonderful husband, and a beautiful daughter. On top of that I have a great job that I love. What more could one woman ask for?
Well there are those days that I sit back and wonder what my life would have been like if I had run off to New York after graduation and worked the stock market floor, or changed my major to History and become a professor. Would my life be any better or just different. I always come back to the same conclusion, I would change my life now for anything.
Sometimes I wonder if we are really striving for more in our lives or are we just yearing for the what ifs of our past?
September 17th, 2009 at 8:46 pm
To your questions; I do wish I was more daring and, I am happy with the life I have.
I am satisfied with my life and where it is going, but I want more from myself in the life I am in.
A great subject for further pondering indeed.
September 18th, 2009 at 1:51 pm
I struggle with this question everyday. Most days my dreams are big and I am looking for the next bear to wrestle or mountain to climb. But then there are the days when I say, I don’t have to be a famous writer or work so hard. I can just hang out an enjoy all that I have. And I feel relieved. Until the urge to kill the bear comes back.
Nice post. Hope to hear from you again.
September 18th, 2009 at 8:16 pm
I am not daring, and I am totally fine with that. Sometimes I wish things in my life were different, but only for 10 minutes or so.