Ten Things I Would Tell My Graduating Self


Graduation season is underway, and a new crop of former college seniors are about to learn that being an adult is a lot harder than it looks.

Just over a decade has passed since I made it out of my university with a newly minted diploma in hand. Since hindsight is 20/20, here are ten things I’d tell my graduating self if I could:

1. “Ditch the ten-year plan.”

You were an ambitious little snot with the best of intentions. But you expended too much energy in working hard, rather than being more strategic by working well. It’s great to have goals and some direction. But just go in understanding that if things don’t work out how you expect, it doesn’t mean the end of the world. It just means the beginning of a new one.

2. “Take a gap year to go abroad.”

I know, you had just graduated with college debt up to your ears. You were anxious about taking any job so that you could start paying those bills. You did what you had to do.

But if it had been possible, I would’ve recommended a gap year abroad. I don’t know if it would’ve made you more hirable, but it definitely would’ve cured some of that wanderlust. Maybe getting a glimpse at how much bigger the world was would’ve helped with some of that anxiety as well.

3. “Have faith in people, but don’t be surprised if they disappoint you.”

People are human, so their capacity for doing stupid things is limitless. Don’t hold it against them. It’s not worth it. There will be times you’ll need to find some grace, too.

4. “Don’t buy the first iPhone.”

5. “Or the first 3-D printer.”

6. “Beware of the entitlement ladder.”

In his book Start. author Jon Acuff warns of the entitlement ladder. It’s a short cut that you think will get you to where you want to go, but it only leads to disappointment. Surer foundations for your career (and life in general) only come with experience and are tempered by time.

7. “Be patient.”

Especially with yourself. Things are not going to work out as planned, and you’re going to make some mistakes. It’s okay. Learn, grow, and roll with it. You’ll have a much better time than beating yourself up over what could have been.

8. “Sleep well.”

Unlike what others may say, losing sleep is not sexy. It’s unhealthy, and your body was not designed to go without restful sleep for long. The deadlines aren’t going anywhere. Get the rest you need, and your work will not suffer for it.

9. “In 2015, Dad will find out he has cancer.”

In 2016, he’ll get the official report that he’s cancer-free.

10. “Go through the fear.”

Acuff called it “awesome.” C.S. Lewis called it “joy.” Whatever it is to you, there’s usually a nasty chunk of fear standing between you and it. Don’t be afraid to go through the fear and get what belongs to you.

Why Ten Year Plans Don’t Work Anymore


I have to admit that when it comes to watching movies, I’m usually about a year or more behind—unless, of course, that movie involves certain DC or Marvel characters or the words Star and Wars in succession.

So, it’s perfectly natural for a movie like The Intern (2015) to completely fly under my radar. I hadn’t even heard of it until a good friend recommended it to me recently. If you’re unfamiliar with it, it stars Robert De Niro as 70-year-old Ben Whittaker, a widower who’s found that retirement is not all that awesome. He ends up getting hired into a unique senior internship program at a fast-growing e-commerce fashion company founded and run by Jules Ostin, played by Anne Hathaway.

During Whittaker’s interview process, he speaks to various (and much younger) company execs. One of the questions he’s asked is a variation of the common, “Where do you see yourself in ten years?” To which he rightfully asks, “When I’m 80?”

But you don’t have to be 70 for that question to be irrelevant. Ten-year plans don’t work anymore for anyone. Here’s why:

There’s No Room for Change

I’m not saying it isn’t good to make plans. Having an umbrella in hand with rain on the forecast is not a bad thing. Good planning helps gives direction, save money and time, and gives scope to metrics.

But tech has played a full deck of wild cards in the past few decades when it comes to how we work. Some hot jobs didn’t even exist 10 years ago. When Pixar worked on the first Toy Story (which came out in 1995—I just made you feel old, didn’t I?), they had computer developers and animators developing the programs to make the movie as they made the movie.

Makes you almost curious as to what jobs will exist ten years from now.

There’s No Room for Awesome

I’m reading Jon Acuff’s Start. at the moment. He uses the word “awesome” a lot. Awesome’s enemy is average. I’m not saying that plans can’t be awesome. Dental procedures going according to plan are awesome.

But living a planned life is not awesome. Success is best understood and appreciated in the context of failure. Innovation is monogamous to risk. Bravery rises in the presence of fear.

Average is predictable. Awesome is adventurous…. We want to plan the road to awesome. We want to talk about our ten-year visions. We want to detail every step before we take a single one. To make sure there’s no room for mistakes or failure. But when we do that, when we squeeze our lives and purposes that tightly, we eliminate any room for surprises…. The road to awesome, though, is defined by surprises. – Jon Acuff, Start., (Brentwood, Tennessee: Lampo Press, 2013), 34-35.

Plans with no flexibility have no room for awesome but plenty of room for disappointment.

There’s No Room for Life

After I lost my job, I was talking with my father about my next steps over dinner one evening. I had sent out resume after resume for months with cricket chirps as my answer, and I was obviously getting discouraged.

Then he asked me, “Why don’t you stop?”


To give you some context, I’d just spent over six years working as an editor in the communications department of a nonprofit. For a majority of those six years, he’d asked me, “So, when are you going to go work for a real company?” But now that I didn’t even have that job anymore, he was suggesting that I stop looking for work all together?

He then told me a story I hadn’t heard of before. I knew that after he was laid off over 10 years ago from his computer programming job, he and my stepmom had opened a cosmetic shop (for her) and a Vietnamese radio station (for him). What I didn’t know was that they had put everything they had into those two businesses. They were in their 50s and 60s at the time. If either small business failed, they didn’t have anything to fall back on. Fortunately, their little businesses became profitable, and they continue to run them today.

I’m sure that back when my father was hired at his last company, being laid off and starting his own business was not part of his ten-year plan. After all, he was from the generation that stayed with a company for decades before retiring.

So, he made a suggestion that I never thought he would to me—to stop looking for work and start building something for myself. He even offered to give me some start-up capital. “And don’t be afraid to fail. If it doesn’t work out, try something else.”

If you’d asked me ten years ago that I planned to lose my job and start selling clothes online, I would’ve asked you to stop smoking whatever mess you were into. Now, I dare you to find someone who has led a perfectly planned life. If you do, I’ll show you someone who is not an expert at living. He’s just been great at not dying (yes, I totally stole that from The Croods).

It’s great to have goals and dreams. We can’t live or grow without them. But we rob ourselves of the joy in the journey to those desired destinations if we plan too much and too far. That may prove the greater failure in the end.