[Addendum] A couple of very promising things happened to me after I wrote this that have made me feel better about things, one of which is the possibility of a job that I really believe I would actually enjoy doing (apparently they do exist!). But even if I don’t get this dream job, my verdict, in this respect, is that I will just have to find a way to strike a balance. I’m sure there’s a way to keep paying the bills while trying to pursue my silly pipe dreams if I can stop complaining long enough to work towards them.


I’ve owned a copy of Where the Sidewalk Ends, by Shel Silverstein, since I was old enough to read it. This is one of my favourite poems from that book:

All the Woulda-Coulda-Shouldas
Sittin’ in the sun
Talkin’ about the things
They woulda coulda shoulda done.
All the Wouldas-Couldas-Shouldas
ran away and hid
from the one little Did.

The more I think about how much I hate the word “should,” the more I realize how often I think about this poem. Considering where I am in my life right now, I think that makes sense. I’ve finished the part of my life that was laid out for me – i.e. school – and now I have to actually figure out what I should do. Unfortunately, I fear that I’ve become so wrapped up in figuring that out, that I’ve stopped doing.

I blame the two voices in my head…

Practical/Pessimistic Me: I should choose a career that is suited to my strengths, with good job security and one that will support me financially. There is nothing romantic about poverty; money matters.

Ambitious/Optimistic Me: I shouldn’t compromise. Why should I settle for Plan B when I haven’t even given Plan A – however unattainable it may seem – a fair chance? There are plenty of people who’ve achieved the kind of things I want to achieve – and many more who’ve failed, I know, but at least they tried.

On odd-numbered days, I agree with Practical Me. I have responsibilities. My mother can’t work forever, and according to my relatives, it’s up to me to support her one day, which means having a steady source of income. Plus, if I never try, then I can never fail. Most days, I’d rather be someone with potential, then someone who tried and failed.

On the even-numbered days, however, I feel compelled to side with Ambitious Me. I fear that, eventually, I’m going to end up in a nice house, with a stylish but fuel-efficient car and a very nice two-tier oven and I’m going to be absolutely miserable. As Howard Thurman said, “don’t ask what the world needs. Ask what makes you come alive, and go do it. Because what the world needs is people who have come alive.” If pressed to choose, I’d have to say that I’d rather be alive… But then again, Howard, that’s easier said than done.

What is the more responsible choice? There is a responsibility that is figuring out how to survive in this world, and understanding that not all things are possible. That sometimes you have to compromise what you want for what you need.

But there’s also a responsibility that we have to ourselves to not let a soul-crushing job and endless commutes and bureaucracy and income taxes and timesheets and printers crush us under the weight of its all-encompassing … sorry, I digress. Perhaps the truly mature thing to do is to refuse to compromise, and to understand that we often create our own limitations – that, or they’re created by others and self-imposed out of a simple lack of confidence or pessismism.

So what’s reality, and what’s negativity? Maybe what I think I just want, is actually what I need?

I sometimes wonder if all the great entrepreneurs and thinkers and politicians and game-changers of the world succeeded simply because they refused to listen to people – including themselves – when they were told that they should try to be more realistic with their goals.

Another quotation… “Some people succeed because they are destined to, but most succeed because they are determined to” – unknown author.

Of course, I exaggerate. Our choices aren’t always so black-and-white. I get through most days by telling myself that I’ll just work at a job I don’t care about until I can figure out Plan A. Or I’ll work on Plan A in my free time, and keep doing Plan B during the day because, well, it pays the bills. Sadly, I feel that it’s a slippery slope and complacency is always creeping up on me. And time is always in poor supply.

I wish I had a more inspiring way to end this post. But I don’t. I’m sure the “movie” way to end it would be to say, “Screw it! I’ll follow my dreams! Now watch me fly!”

Unfortunately, you’re not going to get that. Perhaps the reason so many popular quotations are inspirational and idealistic is because they were said by people who succeeded (or failed, and then later succeeded). No one quotes failures.

…Or maybe this is just one of those odd-numbered days.

I should probably take some time to think this through. Or I should just stop thinking so much and act… But, I mean, I would act, if I could just stop thinking about what I should do…

6 thoughts on “Woulda-Coulda-Shoulda

  1. “Most days, I’d rather be someone with potential, then someone who tried and failed.” – I feel like this all the time. And I love this post.

  2. Yeah, that line stood out for me as well because I really identify with it. But, really, the entire post is very applicable to the thoughts in my head!

  3. I’m stuck in the same… It’s so easy when you have that standard path laid out infront of you when you’re younger. Then you get finished with that and you actually need to decide for yourself. Sure I could have stuck with being a Hearing Screener forever. I loved the job for the most part. I was awesome at it. It made some money, enough to live on modestly alone. However, it wasn’t enough.

    I wanted more than that and this year has been so hard to try and determine if that was the right decision. It’s a different path than my friends close to me. They can’t understand why I can’t do X and Y fun things I used to and explaining I’m poor over and over is exhausting. Thinking that they can get apartments/houses and I won’t for another 3 years sucks. It’s a harder path… but hopefully in the end it means it’ll be a happy path.

    Thank you for your post. Putting me back into this happy perspective. =)

  4. 🙂 It makes me both sad and happy to hear that I’m not alone in this. Let us all keep on truckin’…

  5. This is exactly my current state of affairs – I feel like I took a path that didn’t work out, and now I need to make some tough choices – but I don’t even know what the choice is!

    I feel this is a terrible product of our upbringing as the “Me Generation”.

    I’m with you – and I want to know more about the addendum!

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s