Are You Planning for Career Success or Mediocrity?

(Courtesy of Pablo Garcia Saldaña on Unsplash)

“Would you tell me please, which way I ought to go from here?”

“That depends a good deal on where you want to get to,” said the Cat.

“I don’t much care where…” said Alice.

“Then it doesn’t matter which way you go,” said the Cat.

- Lewis Carroll, Alice in Wonderland

How many of us will wake up some future morning and think, how did this become my career? Is this really what I wanted to be doing?

Probably a lot. Statistics on job satisfaction and workplace fulfillment aren’t impressive. And most of these people weren’t this miserable when they started their careers.

But somewhere along the way they stopped growing and only focused on the daily grind. Their focus went from long-term growth to short-term convenience. And they lost long-term job fulfillment because of it.

Unfortunately, too many people are leaving their career aspirations to chance. But the good news is that those of us who aren’t have a definitive advantage over this wandering majority.

And it’s not difficult to avoid this fate. We just need to be intentional about our career. We need a career plan. A real plan. Not some footnote in a performance appraisal. But a documented plan of action. One designed to help us grow into the career we choose.

You might be thinking, “Yeah Jake, it’s a great idea in theory, but that doesn’t work for me.” Ugh, here come the excuses…

But I Don’t Really Need One

I used to believe that my career would develop itself if I worried about doing my day-to-day job well. But this is only true if our daily activities are developing the skills that we need to achieve my long-term career goals.

As Anders Ericsson explains in Peak, “Research has shown that, generally speaking, once a person reaches that level of ‘acceptable’ performance and automaticity, the additional years of ‘practice’ don’t lead to improvement.”

We learn new skills when we start a job. We have new responsibilities and we need to develop skills to perform them well. But once we can handle these responsibilities, our development stagnates. So we become proficient at handling our daily tasks, but we stop developing skills to further advance our careers.

It’s a risky plan to hope that our daily responsibilities are building the skills necessary for career advancement. Do you want to be good at pushing that button all day? Or would you rather build a different skill set?

But I Just Don’t Know Where I Want to Go

Fair point. Most people don’t know where they want their careers to go. Especially upon starting out. But if we let uncertainty lead to inaction, we’ll never generate a vision.

We need experiences. We need perspectives. We need to try new things and see what excites us. It’s through this experimentation that we’re able to identify our future aspirations.

But Isn’t That My Manager’s Job

I’m happy to encourage career planning with my employees. I’m thrilled to sit down and discuss options and opportunities. I’m willing to provide whatever feedback and ideas are needed to identify and develop critical skills.

But through it all, it’s the employee’s responsibility. It’s their career, not mine. They need to own it.

Almost any manager is willing to help. But if it isn’t important to the employee, it won’t be important to the manager. Period.

But Then What Will Be My Excuse?

Make no mistake, this is the main reason people don’t develop plans. We may give some combination of other ridiculous excuses, but it really comes down to the vulnerability. Even if we don’t verbalize it.

As Steven Pressfield says in The War of Art, “We know that if we embrace our ideals, we must prove worthy of them.”

We all know that we can do our daily tasks well. We’ve proven ourselves in this regard. Whether we can accomplish long-term career aspirations is another story.

For many years, this was why I held back on laying out a career plan. I knew that I wanted to be promoted through management. But I never outlined the specific skills that would support this. And more importantly, the skills that would be needed to be successful at that next level. I worried if I did that, I’d see the harsh reality of my own limitations. So I kept it ambiguous. But ignorance is not bliss. In this case, it’s just ignorance.

Yes, it’s daunting. And yes, we’ll need to face our limitations. But if we don’t start laying out our path, we’ll just keep wandering around. And not like where we end up.

Career Plans Don’t Have to Suck

I recognize it’s easy for me to say, “Plan your career.” Just go plan it and make it happen.

And you say, “Yeah, thanks Jake. Big help you are.”

It’s obviously more complicated. And it doesn’t help that there’s a lot of poor guidance out there.

A traditional career plan will run through a shockingly predictable routine.

  • Complete a self-assessment.
  • Lay out a personal SWOT.
  • And maybe a personal PEST.
  • Compile all our accomplishments since that “Honorable Mention” in our third grade science fair.
  • Then pick our future position. Where do we want to be in ten years?
  • Then come up with goals. A checkbox of accomplishments that’ll lead to this position.
  • Then more goals, but nearer-term this time.
  • Then specify a bunch of metrics. We’ll ignore them later.
  • Then pass out from mind-numbing boredom.

It’s no wonder nobody develops these things.

Monotony aside, this process will eventually lead to some accomplishments. That’s not the concern.

The concern is whether these accomplishments are worthwhile? How do we know that our career achievements will be synonymous with career success?

And as the tens of people who’ve used these plans can attest, they don’t. Because the entire plan is built on actions and accomplishments. Not on the criteria for which we’ll gauge a successful career.

While accomplishments are tangible and easily demonstrated, success is not. It’s a state of being. It’s a feeling of fulfillment. It’s not tied to a specific accomplishment or even a series of them. It’s tied to spending our careers pursuing something that we inherently value.

So while a career plan that focuses on a series of accomplishments is easily measureable, it’s unreliable in gaining a fulfilling, successful career.

If our desire is career success (and if not, why wouldn’t it be?), we need a plan that focuses on that basis. And that comes from a career that’s centered around a purpose. A career where we’re excited to get up every day because we know we’re pursuing something worthwhile.

A Purpose-Driven Career Plan

“Any intelligent fool can make things bigger and more complex. It takes a touch of genius — and a lot of courage — to move in the opposite direction” — Albert Einstein

It all starts with a simple question.

What’s the purpose of a career plan?

To help us make decisions, every day, that help us achieve a successful career.

And if a successful career is considered one that’s in pursuit of a purpose, then our career plan needs to focus on that cause.

In his book, Start with Why, Simon Sinek explains the importance of clearly knowing and demonstrating the reasons behind our actions. It’s our purpose — our WHY — that inspires others and builds loyalty. Our guiding principles and behaviors — our HOW — is the method that we implement our WHY. And our product — our WHAT — is merely the tangible evidence.

When we consider companies like Apple, Southwest Airlines, and Harley Davidson, it’s not necessarily their products which drive the brand loyalty. It’s the identity that they consistently demonstrate. The identity that their customers and employees then adopt for themselves. Which all stems from their WHY.

It’s this WHY that convinces others to trust that we’re pursuing something worthwhile.

The same principle applies to our careers. If we want to develop a fulfilling career, it needs to center around our WHY. That’s our criteria for success and fulfillment.

And our HOW and WHAT are then methods of constantly implementing this WHY into our lives. And demonstrating it every day.

Understand Our WHY — Our Vision

“Clients say, ‘What’s your strategy,’ and I say, ‘Ask me what I believe first.’ That’s a far more enduring answer.” — Ginni Rometty

Most organizations encourage us to set future goals that are positional based. As in, “I want to manage an engineering department by the time I’m 40.”

It’s depressing how terrible this advice is.

Is this really how we want to define our career success? Do we want to limit ourselves to a position?

We shouldn’t want to be a position. People who do confuse titles with authority. They confuse being in a leadership position with leading positive change. They confuse being an engineer with engineering worthwhile solutions.

Positional goals aren’t helpful. At best, they’re a benign distraction. At worst, they’re a significant diversion from building skills that are rooted in our purpose.

Positional goals only focus on the WHAT. They limit our focus to a product. They’re easy to plan for and easy to measure, but they won’t lead to a successful career. They don’t help us pursue our WHY.

So the question isn’t, “Where do I want to be in ten years?” It’s “How do I want to make a positive impact?”

The question isn’t, “What position do I want?” It’s “Why do I want that position?”

What is our guiding purpose, cause, or belief? Why do we do the things that we do?

Simon Sinek’s is to inspire people to do what inspires them.

Mine’s to develop an environment of positive growth, so that people are encouraged to improve and pursue excellence.

It doesn’t need to be complicated. One sentence is enough, as long as it articulates our purpose.

Why do you do the things that you do?

Identify Our HOWs — Our Values

“All men can see these tactics whereby I conquer, but what none can see is the strategy out of which victory is evolved.” — Sun Tzu

Our purpose gives us a future vision. A high-level criteria for success.

But it’s still just a vision. And on its own, it’s not actionable on a daily basis.

Our HOWs are the strategy to implement our WHY into our daily life. They take our purpose and make it actionable.

We need to build our HOWs off our WHY foundation. See what I did there? HOWs, house? Ah nevermind.

This is usually the point that the goal-gurus start up. People telling us to make SMART (specific, measureable, achievable, results-oriented, and time-bound) goals to chart our progress. But they’re still only focused on the WHAT.

And we’ve already established that an accomplishment-based path is foolish. And that’s the path these goals push us toward.

Everyone gets upset when teachers bias their teaching methods to prepare kids for a test. When they prioritize a successful test score over worthwhile knowledge.

But when we focus on goals, we do this same thing to ourselves. We set up some SMART goal for project success. Then goal attainment is the top priority. If we can achieve it without developing our skills, it’s acceptable.

Except it shouldn’t be acceptable. Just as a student who aces the test but hasn’t really learned the concepts shouldn’t be.

Neither path helps us build worthwhile skills. Both set us up for short-lived success and long-term failure.

Instead, we should focus on behaviors. Behaviors, like knowledge, are long-term investments. Their value transcends an accomplishment because we continue to leverage them for future challenges.

People don’t follow us because of our past accomplishments. They follow us because we demonstrate behaviors that they appreciate. Behaviors that are tied to our purpose.

When I see someone stuck in their career, it’s often because they’re chasing accomplishments. And they don’t yet see the futility in trying to check every box on a constantly changing list.

What behaviors, if consistently demonstrated, would support our career vision?

Choose Our WHATs — Our Work

“If you’re not saying, ‘Hell yeah!’ about something, say no.” — Derek Sivers, Anything You Want

Our WHY gives us purpose. An underlying cause that we tie to our career success.

Our HOWs give us a method. A system of behaviors that helps us accomplish our purpose.

Our WHATs are the tangible efforts that we’ll use to implement our HOWs and WHY. It’s the work that we do every day.

So with that, it’s critical that we become more particular in selecting our work.

Too often people accept any new project. Everything’s considered an opportunity. But not all projects will help us obtain career success.

If we agree to take on every project that comes along, we won’t be able to commit to the true “Hell yeah!” opportunities.

When we understand our purpose and know the behaviors that we want to develop in pursuit of that mission, we’re armed with the criteria to decide which projects are worth pursuing.

Does this work contribute to our vision? Does it help develop the behaviors I want to target?

I realize we don’t have full control over our responsibilities. If the GM hands down a job to me, my “Hell yeah!” might become “Aw hell…alright yeah.”

But we often get more flexibility than we think. And we rarely know those constraints until we start to push on them.

What work will help us develop our identified behaviors? What work will be tangible evidence of our purpose?

Act and Evaluate Daily

“Action expresses priorities.” — Mahatma Gandhi

How many people set up a plan, then never actually do anything with it? If it isn’t driving our daily behavior, it’s just collecting dust in a drawer.

Too often, a career plan shows some future goal with plans to check in every couple months to monitor progress.

It’s not comforting to know that we could be off track for several months without knowing it.

Imagine a GPS that says, “Oh, by the way, you made a wrong turn three hours ago.”

Even the best decision becomes obsolete at some point in time. We will eventually drift out of alignment. It’s bound to happen as we overly focus on our accomplishments and decrease focus on our purpose and behaviors.

But it’s easy to correct after a week. Even a month is manageable. It’s a lot tougher to realign after we’ve allowed this drift to happen for a year.

So what criteria can we use to measure whether we’re on track?

What checks can we put in place to make sure our daily WHAT is still connected with our HOW and WHY?

Start Growing Today

It’s easy to wander through our careers, allowing others to dictate our priorities.

Traditional career plans are laborious, and complex, and unreliable. So we don’t do them.

But they don’t need to be. They can be simple, and interesting, and purposeful. They can be an invaluable tool in helping frame a successful career.

  1. Understand our purpose. (WHY)
  2. Identify which behaviors support this purpose. (HOW)
  3. Choose the work that builds on these behaviors. (WHAT)
  4. And grow every day.

There’s no better time to take that first step than now. And start directing our careers toward success.

If you enjoyed this or have any suggestions, please let me know your thoughts. Or if you feel so inclined, I’d appreciate if you could click the 💚 and help me share with more people. Thanks and have a great day.



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Jake Wilder

Jake Wilder

I don’t know where I’m going. But at least I know how to get there.