What Would You Regret Not Doing?

Walking my dog on a brisk, sunny afternoon, I was listening to a book when a question the author posed caught my attention. You know those moments when you remember exactly where you were? I was at the top of the hill in a neighborhood my puppy likes to visit when I heard:

“What would you regret not doing at the end of your life?”

What a backwards way of looking at life, I thought.

But the question stayed with me. It made more sense than the often used exercise of imagining yourself 2, 5, or 10 years in the future. Frequently, that exercise leaves me guessing what might happen and fitting those ideas into cultural expectations.

But what would I regret NOT doing?

I thought through family, time with the kids, friends, more serving, nurturing key relationships, traveling, learning, more learning... hmm, organized learning. Aha! Grad school.

I would like to get a master’s degree. But in what?

The idea of graduate school had been planted, so I casually started looking into programs and places. Who was I kidding? It had to be in the arts. I narrowed the options down to Fine Arts, Graphic Design, and Illustration.

The choices were looking dim until I found something that seemed too good to be true: an online, part-time, two-year program at a reasonable price.

Of course, I immediately set the expectation that I would pay for it with my art. Adding my own hurdles? Totally.
So, it remained one of those long-term, someday-in-the-future goals, while also becoming a motivation to keep creating.

Then a good friend challenged me to think of a different way of doing it sooner. So, hesitantly, I presented the idea to my family. There weren’t any questions, only full support and an offer to help cover the program.
Why didn’t I think of that to begin with?
How often do I make things harder for myself?

Okay, then getting a masters was a go!
But it still felt like an elephant of a goal to tackle.

At the end of April, Saprea happened (you can read about that here). I had a come-to-myself moment where I saw the big wall of obstacles I was so used to building begin to crumble, like I had pulled out the key base Jenga piece. I saw, accepted, and loved all of myself, and I started seeing possibilities instead of obstacles.

Then I found out the program was offering a generous discount if I applied for the May start date.

On a Monday, I spoke with the course advisor and learned that even if I didn’t get accepted, I could use the feedback and apply again. Suddenly it became a no-lose situation.
That same day, I started writing my letter of intent. I polished it a few times, and by Tuesday evening I was sending it to a few trusted people for review.

On Tuesday, I also contacted two of my recent instructors to ask if they would be willing to be my professional referrals, and they both replied by Wednesday.

Curating a portfolio for the program became easier because I already had the foundation of my current portfolio. By Friday morning, I had submitted all the pieces and turned in my application.

Something I thought would take me ages was done in a week. That alone felt incredible, and oh, it felt so good.

Waiting is never easy, but when you hear good news, it is always worth it.
I was in!

But I was already spread thin with several projects. Could I really make it work?
Maybe, if I didn’t eat or sleep. But I knew I would not be any fun to be around. I needed to turn down the discount incentive and postpone my start date. That was hard to do, but the peace I felt afterward was wonderful.

I delayed my start until January.
When winter arrived, I was getting excited and noticed an opportunity for a talent-award scholarship. Funny how I immediately discounted myself. But then my “inner mentor,” I’m sure, said, why not?

I wrote the essay to apply; with no expectations but knowing I wouldn’t regret trying.
And yep, you guessed it: the scholarship was the exact same amount as the discount I had given up back in May.
Synchronicity and a blessing. It still makes me smile even as I write this.

I was so nervous to start. The word “rigorous” kept coming up during orientation week. Was I up for that?
We are almost done with the first module, and despite the short nights finishing the first portfolio, which merits its own blog, I love it!

What’s the saying? When there’s a will, there’s a way.
But maybe the truth is that there are many ways. And I am just an ordinary person trying things out, taking the next step, and learning as I go. Hopefully illustrating (pun intended), that you can go after your own version of a “grad degree”, that thing that keeps calling you, even if it feels too big, too late, or too impossible. Sometimes our happy is waiting just around the corner, or behind the very last hurdle we built for ourselves.

Keep going. You might be closer than you think.

I would love to hear about what came up for you, leave a comment.