On Making it Up As You Go Along (Or, Why it’s Awesome When Your Best Laid Plans Go Awry)

Guest Post by Dana Sitar

You’re recently graduated, between jobs, or ready to take a major leap, and you’re nagged by that awful feeling that you have no idea what you’re doing. You’re reading books and blogs of professionals just months ahead of you, and you can’t believe all they’ve accomplished. If only you had it together like they do.

Here’s the secret:

We’re all making it up as we go along.

I don’t think you hear this often enough: Nobody really knows what they’re going to do next. We’re all always on the edge of the next leap, trying to figure out the ramifications of our next move. The people you envy have just learned to deal with whatever happens, and to embrace the uncertain.

Nothing is as certain as you want it to be.

In a world where new information and networking opportunities are constantly available, you have to be prepared to turn on a dime and follow your dreams. You don’t have to know exactly where you’ll be in five years — in fact, if you try to stick to a clear path for that long, you just might go crazy as better opportunities pass you by.

What if you go to school for six years, earn your MBA, and land some steady accounting job, then discover an inspiring blog, download their free life-changing manifesto, and realize you want to be a painter? Are you gonna stay an accountant? Ew — sounds miserable.

I thought I had it figured out . . . several times.

Early on in my journey, my writing career went through a lot of iterations. I tried to be a copywriter, a ghost writer, a journalist, and a freelance blogger — all sound, money-making career ventures, in the footsteps of professional writers who have gone before me. At each turn I thought I had it “figured out”. “Aha!” I’d say, “This is just what I want to do with my life.”

I thought I was set, chugging along with freelancing and self-publishing. I was “making money writing” — living the dream, right?

But things change. You learn, grow, gain new skills, meet new people, try new things. As I learn more and suss out my true passion, I’m realizing that freelancing for others is not exactly the right path for me, despite a lot of advice to the contrary. The real reason I want to be a writer is to share my work and the passion for writing with others, and “making money writing” has nothing to do with that.

As I write this, I’m facing yet another crossroads. I’ve recently put in my notice with a core client; I’m traveling until mid-June, and I don’t know what my life will look like when I return home to Seattle. I launched my passion project WritersBucketList.com earlier this month, but I haven’t yet sorted out how to replace the money I’m losing by dropping that client. We’ll see what happens! I just know I’m making the right move, because it feels right to focus on my passion.

Not knowing what will happen next can be truly freeing.

I’ve exhausted a lot of paths to find my passion and purpose as a writer. What’s important is that I don’t regret any of the work I’ve done, the experiments, even the failures. If you decide to become a painter, does that mean your six years in college and your years as an accountant are wasted? Of course not! They were all steps on your path; these are the experiences that make you uniquely you.

When you’re not bound by a mirage of success in the years to come, you are free to experiment and change your mind. You can devote yourself fully to something now and move onto something new without regret when the time comes.

Your best laid plans will always go awry.

But that’s not usually bad thing. It’s sometimes the most exciting thing. You can’t possibly know all the awesome opportunities that will find you; you simply have to leave room in your path for them.

Take everything one step at a time. Let yourself build a vision for the future, but understand how it will morph, and know that it’s supposed to happen that way. Stick to following your passion, and you should always be close to the “right” path.

We’d love to hear from you in the comments: 
When have your best laid plans veered off course?
What new insights or awareness did you discover on the other side?

About the Author

Dana Sitar

Dana Sitar is a freelance blogger, author of A Writer’s Bucket List, and managing editor of WritersBucketList.com, a blog and community dedicated to the pursuit of happiness through writing.

Dana shares resources, tips, and tools for writers in search of a path through DIY Writing. Follow her on Twitter at @danasitar.


{ 8 comments… read them below or add one }

Rashida Thompson June 20, 2013 at 11:13 am

I’ve started to just take things day by day. When I try to plan out my life the way it looks in my head, it doesn’t work. After receiving a huge dose of reality post-graduation in 2008, I knew I was facing an uphill battle. 5 years later I’m just taking everything in stride and just making sure that whatever I do, it’s my best. Eveything else will flow from there.


Dana Sitar June 20, 2013 at 8:59 pm

Great attitude, Rashida!


Akirah Robinson June 21, 2013 at 1:07 am

Great stuff. I can give two examples of when my plans got all screwy. First was when I left a bad relationship after four years. I really thought I was going to marry that man, so life was pretty confusing when I decided not to. Second, I just graduated with my Master’s in Social Work and a gerontology certificate. Two-thirds into the program, I met my husband and now I co-own a restaurant. I never thought I’d be a business owner, but my plans definitely veered off course. As Ben says, nothing in life is certain except death and taxes.


Dana Sitar June 21, 2013 at 2:59 pm

Akirah, what a twist! Sounds like you’re happy and doing great work, however unexpected :) My biggest twist came with a relationship ending, too: I divorced my husband after 6 years when I was 25. Taking that leap pushed me to take all the others I’d been afraid to do: quit school, start being a writer, meet new people, and move across the country — I never thought my life could look like this!


Liesha Petrovich June 23, 2013 at 10:11 am

Great insight. Some of the best things that have ever happened to me were not planned. Actually, most of the planned things don’t turn out like I expected. It’s nice to have a general plan, but being able to adapt and evolve is essential.


Dana Sitar June 24, 2013 at 12:48 pm

Exactly, Liesha! I can’t think of a thing that has turned out just as planned; it’s been so much better staying open to change and possibility :)


Cwervy June 25, 2013 at 11:48 am

Great article and insight.

I found the essence of this article interesting, especially when considering it in respect to the millennial generation, as they call us. We were raised with the ever dreaded “everyone is special” paradigm, something we’ve been criticized for since the first wave of us started developing any sort of personality.

I feel as though this paradigm has had an interesting impact on our generation; we were told we could be anything, but it seems most of us applied that to the “big successes” of the previous generation, doctors, lawyers, CEO’s, etc., and ended up a little lost. It is appearing as though our parent’s vision of our future is no longer a realistic venture for many.

Fortunately, I feel as though we are also beginning to find ourselves, and define who we are as a generation and I feel it’s through a mix of having the world literally at our fingertips, and the great sense of individuality our paradigm has instilled in us. Because of this, I feel our generation has a lot of hope at not only finding what they truly want to “do,” but accomplishing it as well.


Maggie@SquarePennies July 17, 2013 at 9:49 pm

You make plans to achieve your goals, but life is what happens along the way. I like to think of my life as a different stages. And no matter what happens, there are opportunities to learn something new. Each person you meet has something you can learn from them. Life is an adventure!


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