The Defining Decade: How to Make the Most of Your Twenties


“How can I make the most of my twenties?”

Most people asking this question are thinking about their twenties the wrong way. 

They’re expecting answers like “Travel through Europe,” “Don’t waste your time at a job you hate,” and/or “Do whatever you want.” 

All of the above are terrible answers. 

Too many young people are led to believe that their twenties are for thinking about what they want to do and their thirties are for getting started with real life. But there is a big difference between having a life in your thirties and starting your life in your thirties. 

Your twenties are the defining decade of adulthood, especially when it comes to your career. Economists and sociologists agree that the work you do in your twenties has an inordinate influence on long-term career success.

Right now, it may feel like you have all the time in the world to earn more money, but data from the U.S. Census Bureau says otherwise. Two-thirds of lifetime wage growth happens in the first 10 years of your career and, on average, salaries peak and plateau in our forties.

U.S. Census Bureau graph showing lifetime wages for males and females

The choices you make as a fresh grad will largely determine your career trajectory. You are deciding your life right now. 

Eighty percent of life’s most defining moments happen by the age of 35, but the most influential events—the ones that lead to success, fortune, and happiness—develop across days, weeks, and months with little immediate dramatic effect. The significance of these little experiences won’t necessarily be clear at the time, but looking back, all these mini events will have largely defined your life. 

To a great extent, our lives are decided by far-reaching twentysomething moments we may not realize are happening at all.
—Dr. Meg Jay

If you’re like most young people, this notion probably makes you extremely anxious, especially because you likely have little to no idea what you actually want to do (or would like to try) to see if you’d enjoy doing it for the rest of your life. 

Dr. Jay describes the feeling perfectly: 

Our twenties can be like living beyond time. When we graduate from school, we leave behind the only lives we have ever known, ones that have been neatly packaged in semester-sized chunks with goals nestled within. Suddenly, life opens up and the syllabi are gone. There are days and weeks and months and years, but no clear way to know when or why any one thing should happen. It can be a disorienting, cave-like existence. As one twentysomething astutely put it, ‘The twentysomething years are a whole new way of thinking about time. There’s this big chunk of time and a whole bunch of stuff that needs to happen somehow.’

Many young people try to avoid feeling this stress by not making any decisions at all, but here’s the thing: “Feeling better doesn’t come from avoiding adulthood, it comes from investing in adulthood.”

I have no idea what you should be when you grow up, and there is no one path to success. But here’s what I do know. 

Regardless of whether you want to be a CEO of a Fortune 500 company, build a small business, become a sales manager, or freelance your way through life, the people who succeed are the ones who develop a foundational portfolio of knowledge, skills, and experiences—let’s call them the cornerstones of a successful career.

These cornerstones will set you down the right path and almost guarantee the launch of a successful career trajectory.


The Cornerstones of a Successful Career Launch

People Management 

Managing Oneself

Self-management means you take responsibility for your behavior and performance. It means being the boss of you. 

Great self-managers cultivate three key skills

  1. Initiative
  2. Organization
  3. Accountability 



Doing your work without always being told or reminded what to do shows initiative

When you take initiative, you do the hard things first, like reaching out to your boss with an issue (and a solution) before she has to address it, or signing up for a course to increase your skill set to do better at work. These are uncomfortable tasks at first, but you do them in a timely manner, without being asked or required. That’s showing initiative. 

Ways to show initiative at work
  • Spearhead a project – Don’t just have an idea. Plan the idea. Start working on the idea. Invest yourself before you get anything. 
  • Propose a solution to an issue [you’re not responsible for]If you see that an improvement can be made, but it’s no one’s job to really do it, just do it yourself, and then propose your solution to the right person. 
  • Take a course – Choosing to develop your skills and knowledge shows employers how motivated you are to succeed.
  • Volunteer – Volunteering is a fantastic way to gain experience when you don’t have any, and it makes you really attractive to employers.
  • Prepare. Make meeting agendas. Plan the next day the night before. Etc.
Ways to show initiative at work


Examples of People Showing Initiative:

Useful “Initiative” Links:



When you’re organized in life and work, you can plan your time and the things you MUST do. You know what’s most important, what should be done first, and what will take the longest. 

It’s also about being prepared and having the things you need when you need them. So if you know you need certain tools or information to complete a task, you make sure you have them before you begin.

How to be organized at work
  • Set deadlines for yourself – Plan how you will achieve your goal. When do certain tasks need to be done and in what order?
  • Time block — Literally schedule your tasks on your calendar.  
  • Use tools to help you manage – Have a key set of tools (even if it’s a paper notebook) you use, and stick with them. For example, I use Trello or Smartsheet for project management, a notebook for my tasks, and I have my paper agenda and work calendar for my daily schedule.
  • Prepare — Prepare for the next day the night before you go to bed. 
  • Learn productivity techniques — There are a ton out there. I’m a fan of the Pomodoro Technique.
  • Create a routine – Create a routine conducive to your lifestyle and job, and then stick to the routine. 
How to be organized at work



Accountability is NOT synonymous with “responsibility.” They’re similar, but not the same thing. 

For example, your manager could assign you the responsibility to complete a task, but you could blame someone else if something goes wrong, so you wouldn’t have to take accountability for your actions. Or, you could decide that you really don’t care about the results so you don’t put in much effort. Again, you aren’t holding yourself accountable to your job. 

When you hold yourself accountable, you take ownership of all of your responsibilities. Being accountable means you take pride in your work and want to do it so well, you reap the best possible results. 

You own the good and the bad. 

If something you’re responsible for doesn’t go well, you do everything in your power to improve for next time, like testing a new process or figuring out ways to be better prepared.

That’s accountability—it’s about your attitude to the task, not whether or not the task is successfully completed. 

Ways to hold yourself accountable
  • Own all of your tasks – When you are given a task by anyone (e.g. a teacher, boss, or parent/carer) don’t think of it as a task someone gave you. Say to yourself: “This is my task. The passion I put into this task reflects on me as a person, and I am ready to take pride in what I do.”
  • Set stretch SMART goals and KPIs for yourself — Set goals and targets, with specific timelines for projects, and make them “stretch” goals/targets to push yourself harder. 
  • Adhere to deadlines — Deliver on or when you’re expected to deliver, never after. Underpromise and overdeliver. 
  • Go the extra mile, and do things as well as you can – If you have been assigned a task or activity and it’s not going well, think about what extra steps you could take to make it better. Is there someone you could talk to? An extra action you could take? A new way you could look at the problem?
Ways to hold yourself accountable

Great achievers manage themselves, they don’t require being managed incessantly by others in order to get everything done. Regardless of your job, you must manage yourself. If you don’t, someone else will, and you definitely don’t want that. 


Managing Up

Sixty-five percent of employees say they’d take a new boss over a pay raise, which isn’t surprising when you learn that three out of four employees say their boss is the worst and most stressful part of their job.

I hate to be the bearer of bad news, but you will experience a bad boss(es) at some point or another, and it’s your job (and in your best interest) to make the relationship work. 

Managing up means managing your relationship with your boss. 

Before you can manage this relationship though, you need to understand your boss. That’s step one. 

What type of manager do you have? While there may be patterns among bosses, many present their own set of issues that require different skills to manage. 

The different types of bad bosses

No matter what type of boss you have, you still need a certain set of skills to successfully manage up, like anticipating your manager’s needs and getting buy-in for your ideas.

Inevitably, problems will arise, so knowing how to bring a problem to your boss is important. But even more important, maybe the most important, is being able to genuinely provide value to your boss. 

Managing up isn’t about sucking up. It comes down to being the strongest employee you can be by creating as much value as you can for your manager and the business. 




T-Shaped Skills

The future belongs to the integrators.
—Educator Ernest Boyer

Growing up, my father always told me that if I wanted to run a business, I’d have to know how to do everything in the business first. But growing up, we’re made to believe that we should just know how to do one thing really well—specialization over generalization—if we want to find a job after college. 

While that may have been true in the past, it’s no longer the case, especially for job seekers. 

UpWork infographic, Freelancing in America 2019

UpWork’s comprehensive “Freelancing in America” study


As of 2019, 35 percent of the U.S. workforce freelanced this year, and that percentage is only expected to increase to 43 percent by 2020 and 50.9 percent by 2027. 

And conglomerates, like Google, already employ more contractors than full-time employees. As of March, Google outsourced work to roughly 121,000 temps and contractors around the world, compared with 102,000 full-time employees, according to the New York Times

Companies are expecting more and more bang for their buck, which means they want “deep generalists” or people who can do a multitude of things well. Why hire a bunch of expensive specialists when you could outsource to one purple unicorn, who can do it all for a better price? 

Nearly all of the biggest innovations have been developed by multifaceted individuals. 

Fun Fact: 15 of the 20 most significant scientists in history were “deep generalists” or “polymaths.” And did you know that the world’s five largest companies were all founded by polymaths (Bill Gates, Steve Jobs, Warren Buffet, Larry Page, and Jeff Bezos)? 

Additionally, more than 10 academic studies found a correlation between the number of interests/competencies someone develops and their creative impact. 

In order to succeed today and in the future of work, you must build atypical combinations of skills and knowledge across fields and then integrate them. 

Study the science of art. Study the art of science. Develop your senses—especially learn how to see. Realize that everything connects to everything else.

Elon Musk is a prime example of a polymath. He’s combined an understanding of physics, engineering, programming, design, manufacturing, and business to create several multibillion-dollar companies in completely different fields. 

And Darwin’s first scientific breakthrough hinged on his comprehensive knowledge on a wide-range of subjects. 

The idea itself drew on a coffeehouse of different disciplines: to solve the mystery, he had to think like a naturalist, a marine biologist, and a geologist all at once. He had to understand the life cycle of coral colonies, and observe the tiny evidence of organic sculpture on the rocks of the Keeling Islands; he had to think on the immense time scales of volcanic mountains rising and falling into the sea… To understand the idea in its full complexity required a kind of probing intelligence, willing to think across those different disciplines and scales.

For the past 10 years, I’ve called myself a “journalist with a marketing mindset,” to describe my unique combination of skills. And clients and hiring managers have always eaten it up. They still love it to date, especially because we’re at the peak of “content marketing.” 

It’s ironic, because in journalism school, all my peers kind of looked down on me for my interest in marketing, as most journalists don’t respect marketers and vice versa. The thing is, what they failed to realize, is that each skill brings something uniquely valuable to the table, and if they combined these skills, they would be a purple unicorn

The launch years are the time to master one (or maybe a few) skill(s) while learning the basics of all other functions of the business. You want to understand core functions, business processes, and how they connect.  

I link to a few more in-depth resources on this topic below, but you may also want to google for more specific articles, based on the type of career you’re considering. For instance, “t shaped marketer” or “t shaped designer.




Powerful Network

Your network is your net worth. 

The above quote couldn’t be closer to the truth. 

I wouldn’t have made it to where I am today, if it hadn’t been for people willing to help me along the way. My network has helped me land jobs, find work, get through difficult times in my career, mentor me, introduce me to important people, and offer invaluable advice. 

The people we spend our time with largely determine the opportunities that are available to us. Or in the words of Rich Stromback, “Opportunities do not float like clouds in the sky. They are attached to people.”

I won’t dive into this topic in-depth (that requires another article), but the resources below should teach you just about everything you need to know in regards to networking. 




How to accelerate your career

Your first job doesn’t have to be at Google or Facebook in order for you to succeed. There are many paths to the top, and none of them really look the same. Regardless, successful people all have one thing in common—they took on jobs/gigs that had the most identity capital

Some jobs give you more identity capital much faster than others, even if they don’t seem too glamourous at first. Think of them as early career accelerators (see below). 


Early Career Accelerators

Sell services to local businesses

This is exactly what I did when I dropped out of college. No one wanted to hire me because I hadn’t graduated, and so I made my dad a website for his local business, which gave me a work example to sell to other local businesses. 

Once I started earning money and experience from the websites I built, I sold clients on marketing services, which I templated, packaged, and sold to more local businesses. 


Lead a project team at a weekend hackathon 

startup weekend websiteAnother way I gained a lot of experience fast was by participating in local hackathons, like Startup Weekend and GiveCamp.

At events like these, you can apply to lead a team, and be responsible for doing substantial work in a short amount of time—you’ll create tangible results that you can showcase in your portfolio. 

For example, at GiveCamp Orlando, I led a project team that built a new WordPress website for a local non-profit in one weekend. 




Work for a startup

We Work Remotely website

I highly recommend working at a startup, at least once, especially in the beginning of your career. 

At startups, you can make a huge impact pretty quickly. You get to wear a lot of different hats, helping you gain a ton of hard skills simultaneously. And if you do your job well, you’ll likely be promoted, as they hire more people, to spearhead a certain project or department. 

Last but not least, you’ll meet brilliant people who are probably smarter than you, in at least some areas. 


How to find startup jobs:


Do pro-bono work for a non-profit

Volunteer Match websiteSearch for work on marketplaces like VolunteerMatch and Catchafire that list non-profits looking for help with specific projects, which you can apply to do pro-bono. 


Build your own side-business

Working a side hustle can help you explore your interests, build new skills and experience, not to mention bring in some extra cash. For more money-making ideas, check out this post.


Engage in niche, online communities 

Rooftop Slushie website

When I lost my job, people I didn’t even know, reached out to me because I posted in niche, online communities. 

Whether you lose your job, need work or just need some trustworthy advice, I highly recommend engaging in niche forums. Here are a few of my favorites. 


Work remotely

Angel List websiteWorking remotely early on in your career is a good thing, because it shows you can effectively manage your time and be successful without someone looking over your shoulder, making sure you get your work done all the time. 

Here are some places to find remote work.


Don’t expect your 20s to be the best years of your life

Many of us go into our twenties with the false belief that this is going to be the best decade of our lives. But in reality we face a bleak job market, poor economy, unfair corporate ladder, and sad dating pool.

Turns out, our twenties are not in fact the best years of our lives—quite the opposite. They’re often the most uncertain and difficult years. 

With this in mind, don’t waste your time trying to make this decade the best of your life.

Instead, invest in these years wisely, because all of the decisions you make during this defining decade will shape the rest of your life. 

Ambition is the path to success. Persistence is the vehicle you arrive in.
—Bill Bradley

So, what are you waiting for? Get to work.