6 Career Lessons I Learned Way Too Late In Life

I graduated from college seventeen years ago. In that span of time from graduation until now, I, like most of you, have had many different jobs and more than a couple different “careers”.

As I look back on my performances in all those roles across those seventeen years there are some bits of wisdom I wish I knew.

These points can be applied at any time in your career; they are not just for new grads to heed.

Also, since it’s obvious, I am leaving off “dress appropriately”, since I presume you all know that already. Even though that’s one bit of knowledge I did not possess early in my career, if you read this site, you are already ahead of the game, sartorially speaking.

That being said, here are the OTHER career lessons I learned way too late in life.

#1 – Put your foot on the gas from day one.

This is the most important piece of advice on this list.

When I graduated college, I stepped into the workforce formidably armed with a liberal arts degree from an unremarkable school. I had just moved to New York City (as was common for pretty much everyone who lived in the tri-state area at the time) and needed a job desperately.

The job I eventually landed was a pretty generic “corporate job”. Grey cubicles, stale coffee, pointless meetings…the whole nine yards. The work I was hired to do was easy and didn’t require much thought. My team leader even told me that once my work was done for the day, I could just sit in my cubicle and wait out the rest of the day (even though I usually got all my work done by 11:00am).

He and I would frequently head down to the city gym on the corner and shoot hoops for a while in the afternoons.

What I’m trying to say was that the first job I got right out of college was EASY.

I stayed in that job for almost two years. My boss was offering me a promotion the entire time, but I didn’t take it because I didn’t want to “mess up a good thing”. This job was so easy that I experienced no stress at work and had predictable hours. I thought that if I stayed at this easy position, I would be able to pursue other passions, like singing and acting.

Unfortunately, the job paid terribly and I was barely scraping by. I made so little money that I didn’t have the ability to do anything outside of work. I couldn’t take voice lessons. I couldn’t go see any shows. I couldn’t try out the new coffee shop. I couldn’t meet up with friends for a drink after work.

The fact that I wasn’t progressing in my career put a handbrake on the rest of my life.

Here’s what I SHOULD have done:

I should have viewed my easy job as an opportunity to get noticed. I should have annihilated my work every day and then gone to my boss to request more projects. Once that promotion became a possibility, I should have jumped at it.

Do you want to know when I actually took that promotion? When my future wife and I started dating and I realized I didn’t have the money to take her out to dinner.  

So why didn’t I put my foot on the gas earlier? Why did I wait two years before I took that promotion? Well, I knew that this job wasn’t my “forever job”. I knew that it wasn’t going to be my career, so I didn’t see any value in putting in the effort.

The gigantic problem with that kind of thinking is that, had I been a man on a mission as soon as I walked through the door, I would have gotten higher pay and a better position EARLIER which would have led to even higher pay and better positions EARLIER and on and on.

It’s like contributing to your 401(k). I essentially wasted two years dicking around not getting my act together. Once I took that promotion, I was two years behind where I could have been.

It didn’t matter that this job and this company weren’t my “forever home”. What I didn’t realize was that progressing in whatever job I had, and it didn’t matter what it was, would allow me to pursue other interests because I would actually have things like money, freedom, and connections.

Speak up. Move up. And then move on, if you need to. Don’t stay with a job or company if something tells you it’s time to leave. Even if it’s comfortable. If you’re comfortable, you’re not growing.

Also, stepping on the gas will condition your brain for hard work, success and hustle, which brings me to my next point…

#2 – If you’re lazy in one aspect of your life, you’ll be lazy in all aspects of your life.

Put another way: You can’t hustle in one aspect of your life if you’re lazy in other aspects of your life.

I kept that easy job for two years because I thought that if I could just coast at work, I could spend my energy crushing my passions.

The problem was that since I wasn’t hustling at work, I didn’t know how to hustle outside of work. I took on a passive attitude from the hours of 9am to 5pm and then expected to suddenly flip on my work ethic like a light switch.

In reality, I was lazy at work and lazy with everything else in my life. I let the fact that I had no money define me and limit me. I felt like a bystander. I felt like a passenger, waiting for good things to happen instead of putting in the energy to MAKE them happen.

You can’t just “hold serve” in one area of your life and expect to go all gangbusters in the others. If you shift your mindset to be successful in one area, you will then, naturally, apply that mindset to every aspect of your life. You’re either driving towards success in everything you put your energy towards, or you’re not.

You can’t be a hard-charging, go-getter with your side hustle and a go-with-the-flow, milquetoast in your 9-to-5.

It just doesn’t work.

#3 – Call attention to your hard work and successes.

No one will notice you if you don’t call attention to yourself.

If you feel especially good about a project you completed, mention it to your boss. Or your boss’s boss. Oh, and make sure you CC them on that email you send your manager when you’re working at midnight on a Saturday… just so they know that you’re working at midnight on a Saturday.

Toot your own horn. Bring attention to yourself. Let people know what you’re doing and what you have completed.

When I worked at that first job out of college, my coworkers who were all at the same level as me always talked about this one guy who was on the team a few months before I started. They would bring him up in a “Oh man, remember John? That guy was insufferable!” kind of way.

Apparently, John would make a big deal of the work he did to the boss. He would pop into the boss’s office every so often to chat about something insignificant. The work was, as I said, incredibly easy, but John made himself visible to the big boss as much as he could, which pissed off his colleagues since they viewed him as a brown-noser.

But you know what? John won an employee award and then left the company after a little while for greener pastures (probably with a great reference).

John probably owns his own company now.

At the time my coworkers told me this story, I agreed that John seemed like a really annoying guy. It’s only now that I realize that John didn’t give a shit about what his coworkers thought of him. He hit the gas from day one, realized the work was stupidly easy, decided he was going to make hay while the sun shone, and bounced to bigger and better things once he had the chance.

I scoffed at John’s efforts… and languished for two years in the role John left in the dust.

#4 – Find a job where you enjoy the grind.

It’s a misconception that you have to pursue your passion in order to be happy. You don’t. If everyone followed their passions, we would all be wine-tasters and professional sleepers.

You DO need to enjoy your job on some level, though.

We all enjoy the fruits of our labor. But the key to not wanting to step in front of traffic at the thought of going to work every day is finding a job where you not only enjoy the fruits of your labor, but you enjoy the labor itself.

It’s like with exercise. We all like looking fit and feeling healthy, but we need to find an exercise routine that works for us. I like weightlifting. I find it fun. So, not only do I like the results I get from it, but I like the work that is required to get those results.

At one point in my career I worked in the marketing department of a large, international, menswear company. I was in charge of the US catalogs and always loved when I would get to see the designs of the catalogs from the other markets (UK, Australia, Germany, etc.).

I would sit down with my coffee and go through each page to see how the messaging differed or if there was anything I could incorporate into my own catalog.

I also loved when the photography for the new season was ready. Or when the Buying and Merchandising teams announced the new ranges.

These are examples of enjoying the grind. I would legitimately get excited when these things would happen at work.

It’s also why I like creating content for this website. I like writing. I like the process. I like sitting down in my comfy office chair with a cup of tea (or glass of beer), turning on some soft classical music on the radio, looking through the window across the mountains, getting lost in thought, and then trying to organize all those thoughts on a computer screen.

I keep a very strict writing schedule for this site. Sometimes it requires me to work early in the morning or late at night. And while sometimes it’s a drag to not be able to watch a movie with my wife after dinner because I need to hit a deadline, I enjoy so much of this grind, that I stay committed to it.

#5 – Comparison is not a bad thing.

We can all agree that social media sucks. For the most part social media is terrible and 99% of it is total trash.

It’s because of social media that comparison has gotten a bad rap. Countless articles tell us to not compare ourselves with the other people we see on Facebook, Instagram, or other social media platforms.

The lives we see on those platforms are not real. The pictures are professionally shot. The locales aren’t real. The “perfect” family consists of an alcoholic dad and a cheating mom.

We are told that comparing ourselves to other people on the internet will only lead to jealousy and heart-ache.

I contend that comparison is a good thing and we need some comparison in order to keep pace in life.

As an adult with a fully-functioning brain, I can tell when something I see online is bullshit. I know that the “perfect” photo shoots aren’t perfect. I know that every family has struggles. I’m not stupid. And neither are you. You know all that, as well.

But it’s ok to look at someone who is a similar age and say to yourself, “Wait a second… So-And-So is my age and already has a house/wife/kids/career. Maybe I should push myself a little harder so I can get those things, too.”

You see, years ago when societies were smaller and closer-knit, everyone compared themselves to their peers and that served as sort of a “cultural norm” for where everyone should be at a certain age. Sure, there were people that didn’t fit that mold, but for the vast majority of folks, those standards were helpful checkpoints for where they should be at any given point in life.

They also served to motivate people.

“Oh, if Bill can make senior manager by 40 than surely I can, too!”

This kind of comparison isn’t wrong. It’s actually healthy. It keeps our fires of competition burning.

So, next time you see someone on Instagram who has a life or job you want, don’t scoff and tell yourself that you’re on your own special path. Use it as motivation to stop scrolling, get back to work, and make your life what you want it to be.

#6 – Don’t be afraid to say the first number.

There is a lot of well-meaning advice out there trying to help you get the most money from your job. When it comes to salary, that advice usually sounds like this: “Whatever you do, don’t say the first number!”

The article or video will tell you that anyone who mentions the first number in a salary discussion is a dope! They’ll tell you that you’re at a natural disadvantage if you show your hand!

The kicker is that they will then give you a monologue to recite to the poor HR person conducting your phone interview about how you “need to further understand the intricacies of the position before I can offer a salary preference” (as if you’re going to remember that in the heightened emotional state you’ll be in while interviewing).

I bought into this view for about the first five years of my professional career before I realized how stupid it was.

When I started out in my career, there was no such thing as Glassdoor. You could look up the salaries of other similar jobs in your area, but the data wasn’t super reliable. Now, however, everyone has access to all the information from the dawn of time. Everyone knows the salaries of every single job on the market. There is no guesswork anymore.

If you don’t know how much you should be paid when you apply to a job, you haven’t done enough research.

When you go into an interview, have a very specific number in your mind for what salary you want. When the person inevitably asks you what salary you’re looking for, all you need to do is… tell them.

That’s it! Just say, “I’m looking for $XX?” and then shut your mouth.

No need to go all “Well, based on my experience and my achievements in blahblahblah, I feel that a salary of $XX is appropriate given the blahblahblah of the blahblahblah…”

Just tell them the salary you want.

They’re not going to laugh at you. Or yell at you. Or tell you you’re stupid. Or immediately exclude you from consideration for the role. They know that everyone is trying to get as much money as they can. It’s all normal and expected. There is no need for the whole song and dance of a back-and-forth negotiation with two parties who are too scared to throw out the first number.

What I am trying to say is that the whole “what salary are you looking for” conversation isn’t as delicate a conversation as you think it is. Just say the salary you want. Stop wasting everyone’s time with your dithering and hand-wringing!

You DO know the salary you want, don’t you? Definitely do your research to see how much you should be paid based on your location and position. But, more importantly, decide on the salary that would get you excited to take the job.

Is there a possibility you’ll leave a few grand on the table if they have more in their budget? Sure. There’s never a sure-fire way to know how much they have in their budget to hire you. But as long as you know the amount of money that will make you happy then it shouldn’t matter.

It will also be a hell of a lot easier to remember in a stressful situation, like an interview. You don’t have to worry about how to negotiate. You just tell them exactly what you want. No need for some ridiculous dance.

When I got hired at that marketing job with the menswear company, I was moving BACK to NYC from working at a small marketing agency in upstate New York (where I had been for about four years). I did my research on what my salary should be since I was moving to a very different location. In my interview, I simply answered the question when asked about how much money I was looking for.

And that’s exactly the salary I got. Looking back on it, I guess that means I could have made more. But I got the exact amount of money I had decided would make me happy. And I was completely satisfied with it.

So, what happens when you give a number and it’s HIGHER than what they had in mind? In my experience, when that happens, the employer says something like “Ok, well the salary range for this job is a little less. It’s actually $XX to $XX.”

At that point, you just say “Ok. I would still like to learn more about the position.”

Make them WANT to give you the salary you want because of how wonderful you are.

Saying the first number puts YOU in charge. It puts YOU in the driver’s seat. It allows YOU to steer the conversation.

It allows you to establish the starting point for the whole conversation.

It also conveys confidence. If you give some weird, wishy-washy answer when asked what kind of salary you want, you’re not going to come across as a savvy negotiator. You’re going to come across as someone who doesn’t know what they want. It’s not a good look.

A confident man knows what he is worth and knows what he wants. Be that guy.

Successfully navigating a career is no easy feat, especially with the added responsibility of children.

Hopefully, no matter where you are in your career, you will be able to apply these bits of wisdom.