Common Dilemmas: What if I Have a Family to Support?

I have a great life. For the most part, I do what I want when I want to do it.

I don’t have a family and my girlfriend, Jessie, and I are fairly independent. Most of the time, I’m the only one I have to think about when I make decisions about my work and my life.

This makes it difficult to answer questions when someone writes in about a problem that involves their family. I’m always vague when it comes to giving advice—I usually ask more questions than give answers—and I don’t like feeling responsible for other people’s decisions; that’s the opposite of freedom as I understand it.

So, when Gabe—an Army Officer with a wife and kids—wrote to me asking for advice on what to do about his career, I didn’t have a great answer for him.

Update: As a few commenters pointed out below, Gabe actually does not have kids. I’m pretty embarrassed to admit I misread his email and never noticed my mistake. That ought to teach me to read a little bit slower!

I want to enlist your help today. Here’s the email Gabe sent me:

Tyler,

I’m a 26-year-old U.S. Army Officer. By most standards, I’m highly successful. Happily married, no kids, making over $60K per year. The catch is, I’m absolutely miserable. I dread every single day I go to work. I’m a bureaucrat wearing camo. I edit PowerPoint slides and sit in endless mind-numbing meetings. I get treated poorly by my superiors, and work over 12 hours a day. I have no life outside my work, and I hate my work.

I have determined, and my wife agrees, that this is no way to live. This October, my commitment is up and I can depart the military. I haven’t had the courage to commit to leaving yet. I feel like I’m suffering Stockholm’s Syndrome. I make good money and am familiar with what I need to do to be successful in the Army. Venturing out into the civilian world is scary. I’m afraid I won’t find work at all, much less work which is fulfilling.

I picked up StrengthsFinder 2.0 (not an affiliate link) in the bookstore recently and the test told me I need to work in a field where I’m valued and paid for my ideas (i.e. journalism, design, entrepreneurship, etc). Before I joined the Army, I adored journalism and writing in college. I did an internship at the Alumni Magazine, and wrote front-page stories for the university newspaper. The catch is, I know I can’t go from Army Officer to supporting my family exclusively on freelance writing. It takes some time to build a portfolio.

When I’ve looked at full-time writing jobs in the area, they require experience or a degree in the field, but I majored in international relations. My father jumped from job to job when I was growing up, never establishing a steady stream of income. We survived, but the stress of his frequent unemployment almost ripped the family apart. I dont want to put my family through that, which is why I think I’m so hesitant to leave the security of the military.

Perhaps you could give me some advice, specifically from your perspective as a writer yourself. How can I bridge the gap? Is there middle ground between starving writer and high-flying feature writer for Time Magazine?

Sincerely,
Gabe

And here’s the email I sent back to Gabe:

Hi Gabe,

Thanks for writing, and thanks for reading, too; I really appreciate it.

While I can’t relate to your situation because I don’t have kids and I’m not faced with a long-term commitment to the army, I can certainly understand the predicament. Essentially, it seems like you have a strong commitment to giving your kids a stable home life, and that’s commendable. The problem is your current solution for the stable home life is quietly strangling you.

From your email, it seems like you’re framing this scenario with only two possible options: venture out into the private sector where you don’t think you’ll be able to find a job doing what you want, or stay with the army where you hate your work.

Neither of those options sound wonderful, but there are probably a lot of other ones that exist in between there that could be more viable.

To answer your question specifically: Yes, there’s definitely a middle ground between starving writer and high-flying feature writer. I, and many people I know, exist in that space. You’re right that you probably can’t go directly from a job into freelance writing and expect to pay all the bills, but there are many ways to at least get started.

Most of the people I know who are like me don’t actually make their money from writing. The writing helps them deliver a message, but the actual business is built on a product or service that compliments it. Does that make sense?

I know it’s tough working 12-hour days and trying to build something outside of that, and I can only imagine how much more work it is to do that with two kids, but there are ways to make the transition that don’t involve cutting off one thing to start another and leaving your kids in the lurch.

I’d suggest looking at the type of writing you want to do, and then see what kind of potential products you could sell and/or services you could offer people that compliment that. There are lots of options, it’s just a matter of picking a couple of them and testing with the free time that you do have.

And maybe you can’t get a high-paying journalism job right now, but you probably have a whole host of other skills that would benefit a private sector job that might give you more leeway to work on the writing business.

Keep in mind this just my opinion, and it’s not necessarily worth that much. In the end, you have to decide what’s best for you and your family. I would only caution that a terribly unhappy father might not be the best one.

Good luck with whatever you decide Gabe, and thanks for your service.

Tyler

We all want more freedom in our lives. We all want to do work that makes us happy. We also want that work to provide for us and, if we have them, our families.

Right now, Gabe feels like his options are limited. But I don’t think they have to be—there’s almost always a “third option.”

What I’d like to hear from you today is this:

What could Gabe’s third option be? What isn’t being considered that might be worth exploring? And how can Gabe get started on something new without sacrificing his family’s welfare?

Let us know (Gabe is reading) in the comments below.

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Image by: Julia Manserova