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Lessons From Your Elders: Career Mistakes To Avoid In Your 20s, 30s, and 40s

Marisa Sanfilippo
Marisa Sanfilippo

Several professionals offer career mistakes to avoid in your youth. Take the advice of your elders. Don't get stuck making them, too.

While the economy is getting better, the job market remains as competitive as ever and let’s face it, no one is indispensable.

With age 30 just around the corner, I’ve learned my fair share of things to do and not to do in the business world (either having been guilty of them myself or seeing others do them).

I’m always amazed by the career stories of those who are older, wiser, and more accomplished than me. 

Here is some of the best advice I, along with some of my elders who have been there, can offer.

These are career mistakes to avoid, whether you're straight out of college or have 20 years in the workforce under your belt.

Related Article: Millennial Takeover: The Workplace Revolution and How It Changes Everything

Your Twenties

Not Taking Risks

I went to a comfortable four-year college after living at home while attending community college.

Stockton University is a great school but it was close to home and even closer to my grandmother’s house.

I hadn’t ever been away from home before and I liked the comfort of living just a short drive away from my parents’ house and a beach (my happy place).

Stockton was safe and comfortable.

When the time came for me to do an internship, I could have done something that I found so scary at 21 years old,  intern in the Big Apple.

Instead, I did internships that were located close to my college and home.

While I learned a lot, let’s get real, my experience interning in publishing would have been much different had I applied for and earned a gig at any of the big name publications I dreamt of having a byline on back then (New York Times, Wall Street Journal, Time Magazine = better than Christmas in my opinion).

Looking back on those days, do I regret not even applying? Seeing that I’ve become successful and am honored to have my byline here, on Huffington Post, and on other notable publications, no, I do not.

But, had I not worked so hard, I could have easily fallen off the bandwagon and ended up working a dead-end job that I hate.

Marisa Sanfilippo Quote

My advice to anyone in their 20s who wants to be successful in business is: take risks.

Now is the time to do it. You are young and likely have fewer responsibilities now than you will in five to 10 years.

If you take a risk now and it ends up not working out, so what? You have plenty of time to turn things around.

I’m pretty sure Oprah, Marissa Mayer, and Mark Zuckerberg didn't get where they are by always doing what was comfortable.

Not Paying Attention to Detail and Missing the Bigger Picture

Admittedly, right out of college, I would miss some things such as a comma or a word here and there a little too often in my writing.

I quickly learned that reading my writing out loud and examining it with a fine-tooth comb was a must.

If you want to get ahead in your career, never do just what is asked of you, always do more.

Constantly look at the bigger picture and evaluate your work. Keep your eyes wide open and pay extreme attention to detail.

Look at your work and try to see it with a different eye. Question what can be done to make it better.

Acting Like You’re Someone Else, Not Asking Questions, and Not Having Fun

"Don’t try to pretend you are someone else; it will look fake and you will not give the best of yourself.

When someone acts naturally, passion for their work increases and the final outcome will definitely be top rated. Find the courage to ask questions and express what you really want.

Also, learn how to become immune to the opinions and actions of others and separate personal comments from work related comments. This will help you mature professionally.

Finally, have fun while you work. People are awake more hours at work than at home, so your office should not be a boxing ring or a suffering journey. Simply do your best to enjoy what you do and you will avoid self-judgment, self-neglect and regret."

- Victor Yacaman, Head of E-commerce, Leonisa

Your Thirties

Not Knowing Your Numbers 

"Whether you own the company or are an integral part of the team, not knowing your company's numbers and focusing on the wrong metrics is a quick way to disaster. Always understand that it's nice to see large top line numbers, but net income is the heartbeat of your company."

- Dustin Briley, entrepreneur, best-selling author, and President of Yoobly

Not Giving Your Work the Value it Deserves

"When I first started out as a freelance writer, I was afraid people wouldn’t take me seriously, mainly due to my age.

At the time, the Internet was just gaining momentum as a marketing tool, so the average business owner had yet to grasp the value of high quality digital content.

As a result, I undervalued my work. The lesson? Don’t wait to charge what you’re worth.

I’d always envisioned running a whole team of writers at Posts By Ghost, but it took me a long time to realize I would never build my business on tiny-pay, time-consuming projects.

At some point you have to cut loose from the crap work, invest in yourself, and approach those top-tier prospects with confidence.

Starting out on your own is hard, especially in an ever-changing and competitive marketplace. If you need more experience, get creative.

Take calculated moves to gain the credentials you need. I’ve been paid in everything from sportsball tickets to shipwreck treasure, and those gigs were well worth the reward, the experience, and the stories.

It was only after I set my sights on the big fish and started charging the true value of my work that I was able to boost my business to the next level. Your time and your work is worth it."

- Niki Robinson, President, Robinson Writers & Posts By Ghost 

Setting Your Income Goals Too Small

"One of the biggest mistakes I see young people making, especially in their 20s and 30s is setting their income goals too small. When you’re fresh out of high school $20,000 annual income seems like a fortune, and then you realize you need more so you shoot for double, thinking surely, that will be enough.

Five to 10 years into your career, you learn that after taxes, living expenses, and kids, even a yearly salary of $60,000 to $80,000 is still restrictive.

Rather than spending a decade to come to the realization that $60,000 does not give you financial freedom shoot for the stars from the outset.

Don’t make the career mistake of not planning to become the best in your profession and accepting less than you’re worth after you’ve earned it.

Consider how you can leverage yourself to own your own business. It’s likely you’ll realize you need much more income than you realize to live the life you dream of. Think bigger."

- Dean Neuls, CEO and Co-Founder of AlgaeCal

Your Forties

Not Leaving Sooner

"When IBM started going downhill in 1995, I should have left right away. I did resign in 2000 in spite of not being sure what I was going to do next.

I knew my choice was to either stay and be the Norma Rae of IBM or to find a new path. All of my co-workers thought I had lost my mind, but I knew by then that fighting for employee rights would be futile, even if we won.

It was an easy decision for me by that point because they had already downsized so much that my phone rang in the middle of the night almost every night and I was so exhausted I was falling asleep at the wheel driving.

They never replaced me. And I have not regretted leaving for even a second.

There is no such thing as job security. If you’re going to bet on something, bet on yourself."

- Gail Gardner, Small Business Marketing Strategist and Founder of

Quitting Too Soon

"Five years ago I decided to launch a small website and YouTube channel around one of my passions,  Microsoft Excel Formulas. You might be giggling now, but I love solving puzzles and coming up with useful Excel formulas fills me with a sense of accomplishment.

I started the site, did some SEO, created about 50 articles and 10 videos. While creating the content was fun, it was also a lot of work and the money wasn’t coming in fast enough (or so I thought back then).

So I dropped it and focused on my full-time job. Fast forward five years. About a month ago I was struggling with a particularly complex Excel formula so I turned to YouTube for a solution.

Unintentionally, I landed on one of my old videos and was blown away. It had more than 400,000 views. Turns out that while I was busy doing something else, my little YouTube channel has grown exponentially.

It now has thousands of subscribers and almost a million page views. It attracts 10,000 visitors every single month. The truth is: if I had just continued to create videos over the last five years I would have probably ended up with one of the most popular Excel channels on YouTube and I would have probably been able to make more than a decent living from it.

Bottom line: don’t quit the projects you are passionate about. Continue creating and promoting even if success takes time. It will come."

- Yoav Ezer, CEO, Bestseller

Not Adjusting Quick Enough to Technology Innovations

I’ve always been a simple man. I had processes in place for my business and they worked well. Several years ago, I started to notice business was slowing down.

My kids kept telling me I needed to ‘get with the times.’ I was fine taking orders for my company by phone and fax and now they wanted me to be on a computer and have a website?

I finally gave in and it was one of the best decisions I ever made. Within months of launching a website, business started to go uphill again.

One of the biggest career mistakes I made in my 40s was not adjusting quick enough to technology innovations. Today, I’m not so quick to write them off and instead am more open-minded.

- Joseph Cole, owner at Locksmith Toronto Ontario 

Image Credit: Fizkes / Getty Images
Marisa Sanfilippo
Marisa Sanfilippo Contributing Writer
Marisa is an award-winning marketing professional and contributing writer. She has worked with businesses large and small to help them drive revenue through integrated marketing campaigns and enjoys sharing her expertise with our audience.