Nine Lessons I Learned in 11 Years of My Career

We are used to seeing nice, tidy numbers like three, five, and “Top 10” when it comes to lists, but life isn’t always neat or tidy. It’s often confusing and seemingly arbitrary. I’ve had some time to think about this since being laid off and losing my job a month ago, so I decided it was finally time to write down some of my thoughts.

The work we do for a living, i.e., our jobs, is a tricky thing. We have to work to earn money to pay bills, support our family, and function generally in society. But finding that perfect combination of talents, societal usefulness, profitability, and passion is nigh impossible, which is why I believe almost all of us spend our careers fine-tuning the mix to the best of our abilities and judgment until we’re retired. That’s what I would hope for most people, anyway. Complacency is a completely different topic for another day.

So, at this particular ambiguous junction in my life, I thought I’d share some of my own experiences as they’ve related to my professional success in the hopes that maybe they’ll reach and help or provide insight to another person, whether it’s five minutes or five years from now.?

1. Trust your gut. I’m leading with this because it’s been effective for me personally. I believe it has much to do with regret mitigation. Usually, the decisions I make for myself have positive outcomes, but even in situations where I might have made the “wrong” decision, I don’t beat myself up or stew over it too long because I can say with objectivity, “Well, at least I trusted my gut.” Simply put, I did what I thought was best at the time.
2. Seek counsel from others. Trusting your gut doesn’t mean you should be stubborn or think that you alone have all the answers, let alone all the correct answers. It’s wise to seek advice from people who are smarter or more experienced than you; and it’s essential to seek advice from people you trust.
3. It’s okay to do what’s best for YOU. Don’t take this as a carte blanche statement to do whatever you want regardless of how it affects others. I am categorically opposed to taking advantage of or badmouthing fellow colleagues in your workplace for personal gain. But I do mean that if you’re not happy with your current job and you have alternatives, you should explore them. If you can find a role or company where you will be happier, more engaged, earning more money, or doing whatever it is that’s better for you, it’s unreasonable that anyone would expect you not to do so. I’ve never understood why “more interesting work” or “better pay” doesn’t seem to be a professionally couth answer when asked why you left a company at a job interview. Not to mention the fact that - in most cases - a company can let you go at the drop of a hat for no reason other than it’s best for them. It doesn’t have to be personal on either side. Isn’t it fair for that door to swing both ways?
4. Proactively offer to help others with their careers. “Proactively” is the key word here. Some people wait until they’re in a tough spot to ask for help. Others still won’t ask even then because they’re too proud or afraid to do so. Remind the colleagues you enjoy working with that you’re always willing to make an introduction, serve as a professional reference, or write a recommendation.
5. Don’t hesitate to ask for help. This goes hand in hand with #4. You shouldn’t offer to help others solely because of the expectation that they’ll return the favor when you’re the one in need. But we all trip and fall from time to time, and when we help each other, it’s easier for all of us to succeed. Asking for help shows humility and sometimes even wisdom.
6. Maintain an up-to-date LinkedIn profile. It seems obvious to me, but maybe it doesn’t apply to everyone. I’ll admit that it’s probably less important if you’re nearing retirement or don’t plan to move around much in your career, but you also can’t know exactly what the future holds and when you’ll be grateful that someone, like a recruiter, was able to look you up easily. Having an up-to-date profile that shows my professional network what I’m up to and where has been invaluable in my career. Of course, if you’re reading this post, you’re likely already good to go!
7. Network, remain open to meeting new connections, and stay in touch with people. We’re not all people persons, but do the best you can with whatever level of extroversion you were born with - or look at this endeavor as a way to improve that particular trait if it’s something you’d like to work on. This can help you step outside of your comfort zone, and again, you never know when you’ll be glad you met and connected with someone. Example: Many years ago, I connected with a recruiter about a particular position, which didn’t pan out. We didn’t speak for 7-8 years, but we stayed connected on LinkedIn, and when he reached out again, he wound up helping me land a new job. True story!
8. Shoot your shot. Apply for the job. Send the quirky introduction email. Ask for the additional responsibilities, compensation, or title promotion. I don’t need to invoke the legendary hockey player and his famous, though slightly overused, quotation; you get the point.
9. Focus on the big picture. Zoom out and think about where you want to be in 3 months, 3 years, 3 decades. I didn’t know what I wanted to do for the rest of my life when I graduated college, and I still don’t. I’m almost 34, and I am a long-term thinker, so I believe time is on my side. But even if you’re 54, I don’t think there’s any justification to rest on your laurels unless that’s exactly what you want to do. We’re all works in progress, and you don’t have to have it all figured out at this exact moment.

One more thing: I’m grateful to have worked with so many great people over the years, and it wouldn’t feel right not to publicly thank some of the individuals who helped me learn these lessons. I’m keeping the list short to emphasize the impact these folks had on my life in one way or another. If I didn’t name someone from a company at which I worked, it doesn’t mean I had a purely negative experience there or that I didn't learn anything from anyone.

Many I consider friends, not just former colleagues; some kept in touch extraordinarily well over a long period of time; some gave me opportunities to develop my professional career when I couldn’t find them elsewhere; one told me something I needed to hear about not selling myself short or settling for a role that doesn’t make sense given my experience and skill set; and one even fought like hell to keep me from leaving when I wanted to take my career in a very different direction.

In any case, these reasons (to name only a few) are why I want to thank the following individuals. I’m starting with the most recent chronologically so there is zero emphasis on placement. If you remove any of them from my whole working career, there’s no telling how different the trajectory of my life, both professionally and personally, would be:

Darren Webb Ryan Farinella James Martin Denise Ribeiro Jason Hennessey Matt McLean Marian Murs? Jake Kurtz Mike Luhning Larry Massey John Yates Brian Santa Barbara Richard Davis

…and of course Gary Vaynerchuk for inspiring me to finally write this piece of content after telling myself I’d do it for two years.