9 Pieces of Career Advice We Wish We'd Had Sooner

I was six months into my first job out of college in the mortgage industry and flourishing. I was making great money while living in Dallas, and before long, I was offered an opportunity to join the New York branch. On paper, it seemed like a great chance for growth and it included a healthy raise. I was so excited that I didn’t ask the questions necessary to understand if the opportunity was a fit for me and where I was professionally.

By the time I reached New York, that $8,000 raise all but disappeared, and based on the cost of living, I was actually making less money. From a cultural perspective, I traded a nurturing environment full of seasoned professionals who were invested in my professional success for a bottom-line-driven environment full of young sharks trying to make their mark.

[I learned] it’s important to carefully evaluate every ‘growth opportunity’ against your skills, values, and personal opportunity cost. Sometimes when opportunity knocks, we have to look through the peephole before we answer.

Like most young professionals, I heard this message but thought, I’m young and still have time, and instead told myself I would start saving consistently when I earned more or finished paying for this or that.

In retrospect, I should have saved 10% to 15% of every paycheck. I’m actually a very frugal person, but frugality doesn’t necessarily equate to money in the bank if you’re not actually putting it there. I could have saved thousands upon thousands of dollars by now at age 35!

When I was in my 20s and working at my second job out of college, I realized three months in that it wasn’t the right place for me. But when I was offered a great opportunity to move from the Bay Area to Boston for another opportunity that I was excited about, I decided to stay at [my current] job because I thought [leaving] would make my resume look flaky or non-committed.

My advice to my younger self? If a job really isn’t working out, find something new and change. Life is too short. It’s the random experiences that make life exciting and will lead to new opportunities.

I started my first business, specializing in entertainment for weddings, out of my college dorm. I was setting up meetings with my clients at McDonald’s because I didn’t have an office, and I also dressed like a typical student—less than professional. I didn’t understand why I wasn’t getting any business, even though I was one of the best DJs in town.

Then a mentor suggested I lose the college attire, and meet clients in a more professional setting. To my surprise, my business started booming: I booked over 4,000 events per year before I sold the business. I have since launched nine successful companies—and I am forever grateful to that mentor.

The biggest mistake I ever made was grinding through my 20s thinking that a job would ever make me [feel] ‘wealthy.’ I’ve worked several horrible jobs, including selling timeshares at a resort and corporate real estate jobs that were absolutely soul-sucking. However, they did serve a purpose in my journey to doing what I ultimately desired to do: write books, mentor people, and speak on the topic of personal development.

If you feel stuck or are growing resentful of your work situation, the solution isn’t to simply quit your job and find another one. Suck it up for a little bit longer, and research what it is you actually want to do. Once you’ve identified your dream situation, begin working toward that end result—while financing it through your existing job.

I started my first successful business when I was a junior in college with my roommate. We were driven and passionate about our idea, but we hadn’t finished our undergraduate degrees, so we were working with advisers who were older and all held MBAs.

What I should have known was that no amount of education would replace the insight my friend and I had into our business because it was our business. But I was young and lacked confidence, so I was too often swayed from my common sense by people who I assumed were smarter because of their degrees. I’ve since learned to trust my instincts because they’ve proven more valuable than an MBA ever could.

One of the biggest mistakes I made was allowing an employer to decide my career direction. I really liked the company that I worked for, but there were only two possible mid-level positions [that I could be promoted to]. Instead of taking the leap to look for more fulfilling work elsewhere, I convinced myself to squeeze my talents into one of the positions.

After a few months, I realized that I had made the wrong decision—and I had to change jobs almost immediately after the promotion. I could have saved myself and the company time and money if I had been honest with myself.

I went to a state university and majored in economics, and my GPA wasn’t the best. Because of that, none of the major financial companies would take a second look at my resume. When I was just entering the job market, I assumed the candidates with high GPAs who got the high-paying jobs were smarter than me—and I convinced myself that I should be satisfied with getting any job out of college.

It was a big career mistake, because I then limited myself to the types of jobs I pursued, effectively accepting lower salaries and doing double the amount of work as those who were making more than me.

As a new college graduate, I chased the money and the title, partially because I thought that it was proof of success—and because my student loans weren’t going to pay themselves. Over the next 10 years, my income grew, the bonuses were bigger, my title was more superior, and my work was more fulfilling. However, with all of that came a tremendous amount of stress and worry about succeeding at the next level.

Then I started a family and my view shifted. I previously commuted over an hour each way, so I could have the better salary and opportunity with a larger company. I was on track for senior-level management, but I saw my family less and less. Earlier this year, I came to the end of my rope.

Recently, I accepted a position with a smaller company, just 10 minutes from my home. The salary is less, the company is smaller, and there is no ‘race to the top’ because I am already there. The stress is less, and I am truly happy with my decision to make this fundamental change. Now I just wish I had done it sooner.