8 Lessons on Starting Fresh From An Incoming Class

What is the value in starting fresh? In the most recent Indiana Jones movie, Indiana and his friends get stuck in a batch of dry quicksand. They fight and fight to get out, but they can’t. Struggling only digs them even deeper into the muck.

I’ve never encountered quicksand, but I’ve always imagined the later years in my life could feel like that — if I’m not careful.

As we go through our lives, we accumulate lots of things that start weighing us down.

Clothes, relationships (some unhealthy), stress, financial troubles, furniture, and more.

Everyone says that the “Real World” is tough, right?

But what if we could avoid the quicksand? What if we could go through each year feeling lighter, happier, smarter?

A few weeks ago, I had the honor of speaking to the incoming class at IE Business School — 250 students from all over the world, all ready to transform their lives through an intense year of studying and partying.

As I spoke to them at the Opening Ceremony and as I hung out with them during a walking tour of the beautiful city of Segovia, the minds of the students seemed bright and eager. They showed me a few things about the value of starting fresh that I’d love to share with you today.


1. Honesty with yourself is the best policy. Being honest with yourself is the only way to know if you need to start fresh. My favorite way to do this is to ask yourself the right questions.

Having the pause and honesty to dig deep inside your own mind and heart is the starting point to starting fresh.

Here are a few questions to start with, for example:

Are you feeling stuck?

Do you dream of something better?

Do you dread going to work everyday?

What do you feel is holding you back?

It’s these very questions that drove many IE students to enroll in the program they’re about to embark on. It’s these very questions that can help you decide the direction you want to go in.

2. A variety of interests yields greater self-knowledge. Over the course of my career, I’ve dabbled in web design, television, journalism, non-profit fundraising, online marketing, novel writing, and more. Having gone through all of these nooks and crannies, I’ve gotten to know what I want to work on — and what I don’t.

Many of the students I spoke with have similar diverse backgrounds. They know what they want after their year-long program, and they’re approaching their experience with that in mind.

Are there new interests or fields you can explore?

3. Small risk can be more than enough. As we walked through Segovia, one of the students approached me with a question about starting a product-based company. I believe she wanted to make handbags, and she was afraid of the massive investment she’d have to make to get started. I questioned her thoroughly, though. I asked her:

“Couldn’t it be possible to start small — to prove there’s a market before investing or finding an investor?”

That way, the product is validated and the investment barrier is pretty much removed. So many people think they need lots of money to follow their dreams, but what if that isn’t the case at all? Would that destroy the barriers to getting started?

4. Value yourself first. No matter how passionately you try to start fresh, to try something new in your life, there are patterns we tend to follow without even knowing. If you tend to identify with working hard, there’s a big chance you’ll bring the same tendencies to your new venture. This is the case for most students I interacted with that day. Whatever tendencies they bring with them to their new lives post-graduation, I urged them to keep one thing front and center: putting themselves as the most important value to keep safe.

5. Use your energies for planning, not worrying. My conversations with the students were always energetic but also always charged with worry. They asked me about all the downsides to entrepreneurship (what they feel they could mess up) instead of all of the upsides.

What I told them was simple: it takes the same amount of energy to plan than it does to worry. I can thank Eleanor Roosevelt for that piece of wisdom. In reality, it’s very true.

There’s nothing that quells my worries more than action.

6. Exploring won’t mean you get it right the first time. There’s an extreme fear of failure out in the world. This is probably due to the fact that we’re all raised to believe we’re “special” and “unique” — beings that can do no wrong. Instead of thinking we always get it right, it’s more useful (and realistic) to think that getting it wrong isn’t so bad.

When you try starting fresh, it’s not necessarily about getting it right — it’s about exploring.

7. Failing small makes small wounds. We might adopt the “exploration” mindset in theory, but it’s difficult to implement in real life. What are we to do when we want to stomach all the failure heading our way? I shared my favorite solution with the students: failing small.

When I started my blog, I didn’t tell anyone I knew about it. When I started my business, I didn’t have overhead for a few months. When I wrote my book, I had zero expectations except finishing it. This way, any kind of failure felt small, and any kind of success felt huge!

Are there ways to make your failures teeny tiny? Would that destroy the barriers to getting started once and for all?

8. Recognize and enjoy your freedom. Starting fresh can be an incredible experience, but one that is usually overlooked. So many of the students told me about their distress at their old jobs and how this new year at IE would grant them a new opportunity.

Sitting in what used to be a convent from the 1500s, the fact that these students were now faced with an opportunity to transform themselves was a point that was mentioned over and over again. They recognized it, and they’re entering this upcoming year by viewing each new experience through that lens. In our own lives, it’s difficult to recognize our opportunities to start fresh. Someone who quits their job is so overcome with stress that their first few days of freedom is spent on a couch, recovering.

Instead, I’d invite us to view these experiences as opportunities for rebirth, for change, for freedom. To recognize it is to enjoy it.


I promised you video, and video is what I have for you today!

In the following clip of my talk at IE, I talk about some of the fresh starts I’ve given myself over the years. Enjoy!

Watch video here

I look pretty serious onstage, don’t I? Next time, I think I’ll smile more and show off my dimples.

But what I was sharing with the students was serious business — even if a lot of it was emotional business.

As I spoke to the 250 students in Segovia, I told them about my constant shift in career choices: quitting a job after two months, dismantling my startup’s team after six months, and so on.

Truth be told, it doesn’t seem to be the most stable of paths… I asked the students:

“Does this make me a quitter?”

Some might say yes, I’m a quitter. But I disagree.

I don’t “quit” — I learn from my mistakes and start fresh, so I can be lighter, happier, smarter each and every year.

It’s what keeps me out of the quicksand. It’s what keeps me safe in the land of meaningful work, surrounded by people who push me to serve better.

I pivot toward happiness. Do you?

I’d love to hear your stories in the comments:

When have you turned a bad moment into a good one by starting fresh?