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Career Advice

7 Tips for Ambitious People to Make The Most of Their Twenties


Schedule your free time first

Like most people who have been working for 20 years, my career has been full of some pretty great moments and some pretty awful ones.

After graduating from college and spending 9 months slinging colorful drinks in poorly lit Baltimore bars, I finally landed a job at a company my parents weren’t embarrassed to tell their friends about.

Unfortunately, it didn’t last very long. Not even a year into the job I made a mistake that cost the company much more money than what they were paying me.

Being canned from my first real business job was a blow to my already shaky confidence. But this time I didn’t stay down for very long. Not even a week later, I was offered a sales job.

Growing up as a shy kid with a stutter, I was apprehensive to stake my livelihood on my speaking abilities. But a little voice kept telling me it would be good for me.

To my surprise, I ended up doing pretty well. By the time I left that company, I’d gained invaluable sales, management, and corporate training experience.

Things were going well as I headed towards the back-end of my twenties and I’d even earned enough money to buy my dream house in Central America. But like most good things, it came to an end.

A few months after my 29th birthday, my ex-business partner’s dad changed the deed of my property and sold it out from under me.

Losing $250,000 hurt. As did the damage I did to my body for the following year or two as I blindly reached for anything to either smoke or drink.

Things continued to go poorly as I began my thirties. But like most bad things, it came to an end.

At the age of 31, I packed up whatever I could fit into a backpack and moved to Barcelona. Despite not being legally allowed to live in Europe, not knowing anyone there, and being extremely short on cash, I figured out a way to make it work.

After convincing a ton of people to give me odd jobs to make ends meet, I was contracted to give a presentations seminar and I met a woman in attendance who shortly thereafter made the questionable decision to marry me.

Since that time, over the last 10 years, I’ve started a handful of companies and I’ve played a part in growing a few others. In between that, I’ve coached hundreds of people and my work regularly appears in places like Business Insider and The Ladders.

This is just the cliff notes version, and I’m sure I’m either forgetting or purposely leaving a few things out. But overall, despite not being what society deems as wildly successful, most days I feel like a success.

This past week, though, while celebrating my birthday I had a realization that made my smile grow even wider: At the age of 42, I’m just getting started as I’m not even halfway through my career.

If I could rewind the clock and be an ambitious twenty-something again, these would be the 7 pieces of advice I’d lean into.

1. Surround yourself with people who see things differently than you

Yes, in order to be successful it sure helps if you get yourself in front of the people who are already doing what you want to do.

Don’t make the mistake, however, of allowing these people to be your only source of inspiration.

If I’ve learned anything in my career it’s that sometimes the best lessons come from the most unlikely of places.

The 20-year-old intern in your office who had to fight like hell to get an opportunity — any opportunity — may turn out to be the best person to teach you the true definition of grit.

The 30-year-old woman you work with who is raising two kids on her own may turn out to be the best person to teach you about commitment, productivity, and how to properly prioritize.

The 40-year-old designer who beats to their own drum may turn out to be the best person to teach you how to see things from different angles.

So, by all means, listen to Gary Vaynerchuk to get pumped up. But leave yourself plenty of time to get to know people who have lived a different experience.

Amazing things happen when two people from completely different worlds come together and simply talk. From my experience, it is the fastest way to have 1 + 1 someday equal 57.

2. Smile when doing a job you hate

A lot of the recent college graduates I speak with feel frustrated because they aren’t doing the work that sets them on fire. What they fail to realize is most mortals aren’t born knowing what they want to do with their lives.

In fact, most people I know who are doing work they are now passionate about discovered their spark by getting clear on what they didn’t want to do.

Remember this when you feel stuck in a dead-end job. Remind yourself that everything is temporary.

Then do whatever you can to learn as much as you can about the work you do not enjoy as over time it will give you tremendous clarity regarding where you should be spending your time.

Plus, complaining to people about your shitty job is the fastest way to ensure they won’t think of you when they hear about an opportunity.

One of my mentors, Conor Neill, said it pretty darn well —

“If your network isn’t bringing you 2 to 3 good opportunities a year, it’s either time to build a new network or change your attitude.”

3. Work in as many different environments as you can while you are still young

Everyone loves to read about the person who struck out on their own or dropped out of college and created a successful company. The main reason these stories are so attractive is that they’re damn rare.

Again, if you’re one of the few people who knows exactly what you want to do and already have a skill set that matches your clarity, go for it. But if you’re not that person yet, go easy on yourself and follow your curiosity into as many situations, sectors, and verticals as you can. Then be a freaking sponge.

Doing so will help you to accomplish four things that will make your life easier as your career advances:

  • You’ll meet a ton of interesting people and create diverse groups of friends.
  • It’ll speed up the process of determining the work you really do enjoy while uncovering the jobs that sound better than they actually are.
  • You’ll learn transferable skills that will help you stand out in new jobs.
  • It will keep your career exciting as we tend to learn the most when we are beginners.

If you had told me that as I scared stuttering kid that one day I’d be a career/communication coach whose work would take him all over the world I wouldn’t have liked you very much.

But that’s exactly what slowly happened.

You do not find your dream job. You make it by trying as many things as you can and by having faith your career dots will one day connect.

4. Pay special attention to your bad bosses

Throughout my career, like most people, I’ve had my fair share of bad bosses. This was frustrating at the time. But in hindsight, these experiences turned into a goldmine.

This is for the simple fact that through both their actions and their words they taught me what not to do or say when both leading or simply interacting with people.

Please don’t interpret this as me encouraging you to stay at a job you do not like with poor management. Just take the steps to make sure it isn’t a total waste of time by keeping track of the actions and behaviors of others that turned you or the people around you off.

Like I’ve implied multiple times in this article, it becomes much easier to find the right path if you do not make any wrong turns.

5. Leave plenty of white space on your calendar

Legendary business coach, Dan Sullivan’s number one recommendation to people in their careers is to leave 30 percent of their day unscheduled.

As you can imagine he gets a lot of heat for this suggestion. This is especially true from fast-moving entrepreneurs who claim that they need all 24 hours to maximize each day.

Despite the push-back, Dan’s logic makes sense.

First, prioritizing your free-time first will force you to get clear on what tasks are truly necessary for the time you do have to work.

Secondly, it becomes very hard to see the opportunities around you if you’re only looking at the work in front of you.

Thirdly, it will help you to not burn out.

Explore your side-interests with the same level of commitment as you do your job. Learn an instrument. Go to events in your area about any topic that does not involve your job.

You may just find that your learnings outside the office are the very thing that propels your work forward while at work.

This may seem random but learning a foreign language helped me develop the most important career and life skill of all: how to listen.

This is for the simple fact that I’d never be able to say a word if I didn’t first give my full presence to the people speaking to me.

In short, don’t be so ambitious you become one-dimensional. It’s boring.

6. Take the hard steps to improve your communication skills

Take a moment to think about the most successful people you know. It’s not a coincidence that the majority of them are strong communicators.

This may not be fair, but it is reality. The world rewards those who do the work to learn how to properly engage and persuade the people around them.

“If you can’t communicate and talk to other people and get across your ideas, you’re giving up your potential.” — Warren Buffett

Start by doing the annoying work of writing down the answers to the 20 most common interview questions in your sector and recording yourself on your phone giving the answer. Then take the hard step of asking someone who will give it to you straight to critique your work.

This one exercise has the potential to pay you hundreds of thousands of dollars over the span of your career as most people have no idea how to properly prepare for an interview.

Once you’ve gained your confidence from doing that, suck it up and invest in a public speaking course. In only a few sessions you will learn how to tell a compelling story, the power of body language, and how to use your words to move people while also receiving a masterclass on what shouldn’t be said.

I’ve written a ton on how to improve your communication skills in the past. The 2 investments above, however, are without a doubt the most effective as they will fill you with the confidence to do just about anything.

When it comes to career advancement, relationships are everything. Learning how to properly communicate both your thoughts and your feelings plays a massive role in this.

7. Live as lightweight as possible

The best piece of career advice I ever received came from one of my earliest managers. It may sound overly simple but if done religiously it will alleviate an enormous amount of stress in your life: Make your coffee at home.

Money is not the most important thing in life, but it matters in a big way as the world is getting more expensive by the minute and high salaries are shrinking by the second.

Remove yourself from this race by putting 10 percent of whatever you make each month away. Much like scheduling your free time first, prioritizing your savings first will allow you to take some risks without being buried in anxiety.

Move back in with your parents if you have to for a few years to save up cash or pay off your student debt. If that’s not an option, get roommates and pre-game at home before going out and share each other’s food and clothes if possible.

The best decision I’ve ever made in my career was moving to Spain. If you are anything like me and location matters to you and you prioritize the quality of life just as much as you do your work, be freaking frugal.

There is nothing you will regret more in life than not doing what you wanted to do because you made the decision to drink Chocolate Caramel Vanilla Lattes every day.

Oh and one last thought. Unless someone does something like stealing $250,000 from you, do not burn your bridges.

People do stupid things in their 20’s. God knows I did. But despite what people say, some people do change.

Making the choice to forgive people will provide you with one of life’s greatest joys as you get older: seeing people randomly weave their ways back into your life.

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