It's time for a career upgrade

Do you want a fast career... Do you want to earn more money... Do you want to receive more benefits...

This is a message to those of you sitting in your office right now wishing you worked somewhere, or for someone, else. At the very least, you’re wondering if you’re in the right role, at the right company or doing the right thing with your life and your career.

We all see the social media posts demanding you do more, bigger, better things with your life. Pluck bits and pieces of wisdom from podcasts from the Tim Ferris’ of the world. Read articles like these. You have an overabundance of content around you pushing you to feel empowered, to seize the day and all that. You’re digesting it, so you’re obviously looking for something.

At some point in the recent past, you've thought deeply about your career and asked yourself, "Is there more? Should I be wanting more?" Yes.

It’s called a career upgrade. And the best thing about deciding to upgrade your career is that you get to define what that means – it won’t be a path like the person next to you. Before making an upgrade, here are six questions to ask yourself. Perhaps there are millions more. I welcome you reaching out to me to share them.

What is my philosophy?

When I first jumped into the workforce, the most frequently asked question in interviews was “Where do you see yourself in five years?” At first I answered those honestly and innocently. “Well, I can see myself adopting a dog, hopefully by then I have a job that I love, maybe one or two direct reports, a great relationship with someone and money in the bank to travel to far off places on my approved vacation days.”

Later, I learned the game that is interviewing. The answer turned into, “Well, here of course! I’m going to be running the show, leading the pack, winning all the things. I hope to be your right hand man and work all hours to prove to you I can be all you want me to be. We are going to infinity and beyond, you and me.”

Dumbest question ever!

Truth is, no one really knows where they will be in five years (financial projections aside of course, I hope you hit all those goals and more). And if you have an idea, and actually hit that goal, I dare say you didn’t reach far enough. That’s perfectly vanilla.

When I talk about having a philosophy, I’m talking about developing a general veering of direction in how you want to design your career. You can skirt in and around and outside and upside down within those parameters, but the whole time, you can deeply respect and honor your personal philosophy. When you take a job, you need to be taking it for a real reason – and it needs to be a smart one for you.

Is it for the management experience? The expansion of your business network? For the money? Sit down and envision what you want to be when you grow up, in a year. Do you want to be registered in grad school by that point? Do you want to be at a different company entirely? Try a new industry? Do you want to work in a different department on a different project? Your next career move needs to happen with intention and centered around things that matter to you.

Do not just take something simply because it’s offered to you. Do not stay with the same company simply because that’s where you’ve always worked. Do not get up and blindly leave a company simply because people like me write the sentence I just wrote. When you get to a certain point in your career, if you want and design this to happen, you will have many offers handed to you at one time. If you have a philosophy around your career, you won’t stray at random. You’ll always be strategic. But your decisions will happen beautifully and organically.

Is this the boss for me?

I cover a lot of boss conversation. But I’ll expand a bit as it pertains to your career move. Do you have the boss for you right now? Do they support you, serve as an obstacle blocker, challenge you, cheer you on? Do they reward you appropriately, listen to you, push your career forward? When you think of the career your building with the boss you have right now, are you on a merry-go-round or a space shuttle with this person?

If you’re committed to taking a new role, whether in your organization or out, you must consider the boss relationship a two-way street. Interview them fiercely when you're looking at new jobs. And hold your current employer accountable. Of course they're human too, so once you do decide to marry into that relationship, give them a break when they need it (much like you wish to have one some days). But make sure you’re constantly checking in with yourself and you’re constantly demanding the best from the person who manages you. You need communication, expectation, grace, reward, advancement and overall – you need respect.

We don’t know much about your next career move, but we do know this. It will have a boss. Even if you’re launching your own company, you will have someone to answer to – customers, investors, partners, etc. I love Tim Ferris’ approach to eliminating his clients in the 4-Hour Workweek. In one exercise, he stopped contacting 95 percent of his clients and fired 2 percent of them. From there, he doubled his income and dropped his work from 80 hours a week to a mere 15. You are empowered to fire a boss too, whoever that may be in your situation. I promise your life will be better, and you'll find yourself complaining less.

Really, communication is key here. That, and you firmly understanding you deserve respect from where you're sitting too.

Am I escaping?

This is more about the “why” than anything else. Why do you wish to leave your position, why do you want something more, why are you even reading this? If any of those answers is because you’re hitting the ripcord and you’re abandoning ship out of hate or distaste for someone or some project, you’re likely not going to upgrade your career in the process.

At best, you will be manually forcing yourself to take Plan B. At worst, you’ll be settling for Plan C, or even D. These are duress choices, because you’ve chosen to act in a dark, unlit tunnel of fury – no one makes good decisions in a dark, unlit tunnel (I’m assuming).

I’m a firm believer that the best way to do business is through relationships, and if you’re “escaping” a company, you will likely not keep those relationships. Take time to calm down, have conversations, give yourself space. It might be a sign you're ready to leave, but I recommend you leave when you're in control.

Is this comfort talking?

Comfort can be a great thing. Warm blanket, Netflix, pizza. Your closest friends gathering at dinner after a long work day. Knowing exactly who will answer a text when you really need them to answer it. Someone nodding and agreeing to your profound statement. These are great comfort things. This is pleasure.

Comfort can also be a terrible thing. Staying at a company in a dead-end role because you feel like you’ll be betraying a great boss. Not flying out to another city to interview for a new position. Not taking a promotion or project because although someone believes in you, you personally don’t think you’re capable. Not sitting and having dinner alone sans technology because you think people will look at you like you’ve got three heads. This is fear.

If you’re interested in making a career move and you keep second-guessing yourself, it’s highly likely you are experiencing a comfort issue. By reading and agreeing to what I just said, you’ve already indicated you want to make a career move. Which implies fear may be your only problem here.

Let me calm some of the fears. Your favorite boss will be there for you even when you go. They’ll just become a mentor (and those relationships always get better when you’re not officially working together, by the way). You might be turning down the job of a lifetime because you’re unsure of moving to a new city. You might be sitting there with a current situation you aren’t pleased about, letting that control a situation you may absolutely love. 

Gather awareness about your reasoning. If you’re pushing back on yourself when the rest of the world is encouraging you, there’s your sign.

Am I ready to earn more money or authority?

My wording is intentional here. Earning is vastly different than making. If you want more money or more authority in your career, you must be ready to earn it. To put in the hours, the sweat, the emotions, the legwork, to make it a reality.

Halo Effect suggests you've happened upon a great gig without being qualified to take it. Imposter Syndrome twists that on its head and suggests that more than 70% of all successful people you know and love think that they are not worthy of the promotions and work they get. That happens often, and to so many people. Neither are a death sentence. To both, I lean on my favorite idiom, “bite off more than you can chew, then chew it.” Be done with it. If anyone doubts your skills for a new position (this includes yourself), then you’ve clearly made a jump in the right direction. Congratulations. Now get to work.

Do I know the environment?

You’ve already tackled the part about hastily making a decision, but here’s where you need to determine the environment around your choices. Things to consider before you look for a career upgrade:

? When your next bonus is arriving. Maybe it makes sense to wait it out.

? Are you putting your company at a handicap with the timing of your potential exit?

? Are you exploring other departments at the worst time ever in your organization?

? Are you asking for a raise while your company is experiencing layoffs?

? Is it the holidays? Yeah, don’t quit over the holidays.

? Are you prepared for a negative response from the company?

? Are you prepared for a counter-offer from your current company?

Answer all the questions above and think of more, as you assess your next career move. Seasons matter, time of life within a business matters, the happenings around your role and your relationships matter. In the perfect world, you’ve designed your move months before you depart. And in many cases, you can move around within your organization, so you may not have to consider many factors.

Careers don’t just happen. Most of the successful people you’ve ever met, even if it doesn’t appear this way, have mapped out their next steps already. It may seem to you that luck and fortunate conversations happen at random for them, but it does not. Those are months, often years in the making. You can’t count on that happening -- you have to build it that way. If you wish for a different career situation, in your company or otherwise, stay one step in front of your competition (which in many cases, is just your doubting mind).

Manage your career, or someone else will.