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5 Purposeful Questions Every Graduate Should Be Asking

File photo of a young undergraduate waiting to receive his degree at his graduation ceremony.
File photo of a young undergraduate waiting to receive his degree at his graduation ceremony. | (Photo: Reuters/Brian Snyder)

When I graduated from college, I felt overwhelmed with questions.

"What am I going to do for work?"

"Where am I going to live?"

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"How am I going to pay rent, all the bills, and somehow also pay off my college degree that isn't exactly flinging open the bank vault for me right now?"

Then the real kicker question -- "Where do I even start? What are the questions I should be asking?"

That final question was the real punch in the gut, making me feel more nauseous than the three pieces of graduation cake I consumed with the green icing that had encouraged me to "Catch the wind in my sails," right before it was journeying down into my stomach.

I'd spent four years and thousands of dollars preparing for this moment, and yet as I climbed all those steps and flung open to the doors to the rest of my life, I didn't even know where to start.

I quickly realized I wasn't alone. The statistics about twentysomethings right now are pretty startling; with around 25-30 million twentysomethings living back at home with their parents, the highest percentage ever recorded in the United States. (US Census Bureau) Plus, Millennials are earning less in their twenties than any generation before, and 88 percent of minimum-wage workers are 20 years or older, with 4 in 10 of those workers college graduates. (Pew Research and NPR)

So for the last decade I've dedicated my life, through my website, publishing three books, and adding onto my tab with a Masters degree, to figuring out what questions we should be asking as we graduate college and journey through our twenties.

 5 Purposeful Questions Every Graduate Needs to Ask

1. What's the best way to break-up with myself?

Life transitions in general are much more difficult than we give them credit for. Just like breaking-up with someone you thought was "The One", when you graduate college you're breaking up with many different things at once -- a place, a time, a season of life, friends you thought you'd have forever, and in a way, you're breaking up with a version of yourself.

Yet, there's something of strange significance that happens to us when we're stripped of everything we used to depend on.

Maybe transitions aren't something to fly through, but something to marinate in.

Don't just make it through a transition—make the transition matter.

Transitions are not simply a bridge to the next important season of your life. Transitions are the most important seasons of your life.

You learn the most when you're the most uncomfortable. Your senses are the most alive when you feel the most lost. As I write in my new book 101 Questions You Need to Ask in Your Twenties, "your twenties aren't about them going as you planned. But how you adapt, change, and grow when they don't."

2. If I'm going to pursue a big dream, am I willing to drive a 1993 Honda Civic Hatch back with no power steering, no air conditioning, and no right mirror for 15 years?

Pursuing something bigger than yourself will cost you something.

Thus, why I posed this question in Honda Civic Hatchback terms because I've been driving it since I was a senior in high school. And let me just admit that I'm just a few years north of high school graduation. And that Honda is currently running north of 240,000 miles!

So if you're going to pursue a big dream, what are you willing to sacrifice? What are you willing to give up, and what are you going to cling tight to?

If you're going to dream big, are you also going to be faithful in the small?

In your career, your relationships, your life—what's going to be your Honda Civic Hatchback? Functional, yet not exactly something you're pulling up to valet parking.

3. How do I stop networking and start "relationshipping"?

Networking events feel like going to prom all over again, except you didn't even come with a date this time. And you might be feeling even more self-conscious than you did at seventeen. (I didn't believe this was possible either!)

Yet, there's nothing more important to invest in after college than your relationships. But let's stop networking to make it happen. Let's start relationshipping instead.

Let's stop networking like a machine and start "relationshipping" like a person.

Some of the ways I define "relationshipping" is building relationships when you don't "need" them. Meeting another person and being more focused on asking them good questions than you giving profound answers. Checking in on people and giving real, meaningful, compliments.

Basically, networking often feels like asking, "what can these people do for me?" Instead, relationshipping asks, "What can I do for them?"

4. Where's the future of work headed, and what does having a successful career look like today?

A successful career path looks much different today than it did in the past. The days of climbing the corporate ladder to get to the top is now filled with broken rungs. I created a full diagram in 101 Questions You Need to Ask in Your Twentiesof what a successful career path looks like now -- a strategic journey from island to island, picking up specific resources and skills along the way.

If you're not changing your expectations of what today's new career path looks like, then you might end up stranded on an island you never wanted to be on.

5. How do I make a choice when I don't know what to choose?

Graduates today more than ever are overwhelmed with information. With research. With a million different sources, reviews, and searches we could do to find the perfect answer.

Yet, there is no perfect choice. No perfect path. Sometimes the most perfect path is the imperfect one that you're willing to walk down.

So if you're not sure what to do with the rest of your life, that's normal. You're not really supposed to. So instead of figuring out the rest of your life, let's just focus on what you need to do tomorrow.

As Oprah once stated as her key advice for young people to ask themselves, "What's my next right move?"

Make a choice that you're going to make a choice.

Find your "I'm 77% sure" and give it a try. You won't know how it's all going to work out until you start doing the work.

If you're struggling to figure out what your passion is and what you want to pursue, pick something. If it doesn't work out, that's great. Well, maybe not exactly great. But as I write in my book 101 Secrets For Your Twenties, "Your twenties are a game of emerging adult elimination. Every time you cross something off the list, you get closer to naming a winner."

Don't worry about everyone's "success" on social media. There's an ugly side to every amazing picture they're posting. Don't let, what I call, Obsessive "Comparison" Disorder take over. Focus on writing your own story instead of trying to live someone else's.

Climbing through your twenties can feel like being a pug trying to scale a mountain. It's loud, ungraceful, and it feels like all eyes are on your slow climb.

But one tiny step after another, you'll make it to the view you forgot you were climbing for. To everyone's disbelief, including your own. I promise.

Paul Angone is the best-selling author of 101 Secrets For Your Twenties, 101 Questions You Need to Ask in Your Twenties, a national speaker, and the creator of, which has been read by millions of people in 190 countries.

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