(Personal) Career Reviewing and Planning

I did something for the first time this year that you may want to consider doing yourself: a career reviewing and planning session.

Written By
Drew Weilage
January 17, 2020

I did something for the first time this year that you may want to consider doing yourself: a career reviewing and planning session. For myself.

It was a bit like an annual job review. Only that it was conducted by me. And free of bureaucratic rigmarole. 

Started. Completed. Useful.

Why I did it

While most of us have something of a formal assessment for our individual job performance—an exercise which may or may not include the opportunity to discuss where we're taking our careers—annual reviews from bosses are something of a low-value exercise.

"Telling people what we think of their performance doesn't help them thrive and excel, and telling people how we think they should improve actually hinders learning," write Marcus Buckingham and Ashley Goodall in an all-around excellent Harvard Business Review article detailing (with research) why feedback rarely works as well as we'd think it would. 

You should read why for yourself. My summary amounts to this: no matter how hard we try, our feedback to another person is always shadowed by our own biases, beliefs, desires, experiences, and other judgement-clouding realities. 

That's not so good. And that argument doesn't even include the fact that these conversations are guided by the organization's goals—often not aligned with our own—nor the idea that when compensation is connected to assessment, as it too often is, impartial judgement is next to impossible.

Add it all together and it leaves one person truly capable of assessing our performance: us. 

Which is good. Because it's also us who can best recognize the career path we're on. 

This year, rather than achievements or pursuits, my path centered on two questions: 1) Why is work (in healthcare specifically) the way work is? and 2) What can we do about it?

Through the Work emerged as an effort to collect and share the answers. And there's one lesson—perhaps the most important one—worth highlighting here and now and it's this: learning is central to performing the day-to-day responsibilities of any job. 

If you want to get better at your job or prepare yourself for the next one or just figure out how to be more successful: it's learning you're after. So am I. And in this context, doing career reviewing and planning was a natural outcome of that (very important) lesson.

In the end, it was a useful experience I anticipate will be made even more so as the year unfolds. And of course as next year approaches.

How I did it

I once worked for a boss who told me I didn't know how to set goals. "How can I measure your performance if you don't know how to set goals?," they asked.

They, of course, were talking about SMART goals, a framework we're all assuredly aware of. 

And frankly, I wish I would have answered their question with one of my own: "How will you judge my job performance against goals sure to become irrelevant to the work I'm doing?"

In my experience, SMART goals can actually be quite dumb in a dynamic environment when what is important now may not be in a year. Twelve months is a long time. A lot can be learned. A lot can change.

So while SMART goals have their place, I knew my reviewing and planning required more of an organic approach. Something more in line with Jason Fried's philosophy and summarized best by this Jim Coudal quote:

The reason that most of us are unhappy most of the time is that we set our goals not for the person we're going to be when we reach them, but we set our goals for the person we are when we set them. 

Yes, that. 

So I started with a blank sheet of paper and spent nearly two hours thinking about last year and this year, the path I'm on, and how I want to steer it.

Here's the framework I used:

It worked quite well. Though I'm certain I'll adjust how I do this in the future because that's what learning does: helps us find better ways to do things as a result of doing them. 

Although the framework is presented linearly, I didn't hold myself to working through it in a formal step-by-step manner. That's just not how the thoughts came to me. 

Instead, I used six sheets of paper (one for each of the above and the sixth for the general/random/parking lot thoughts that came as I went...) and jotted notes in the sections where I thought they belonged.

Here's how I guided my thinking.


I spent the most time here and asked variations on the question: What happened last year?

I started by thinking about bullet point projects. Those accomplishments I added to my resume in 2019. That led to a number of additional thoughts including:

Then I used questions to get my thinking moving in different directions and for recalling memories. If I had direct answers to a question, I wrote those down, otherwise they were just for rumination. I suspect the list of these questions will grow over time.


This was a low-pressure question and I intended for the answers to come easily. Over time I've found the "Where am I going?" question can be filled with anxiety, and when it is again, I expect it to be useful to explore that. But I also wanted a question that could just as easily be answered "figuring it out as I'm going."

Before I began reviewing and planning, I knew there were things I wanted to do and wrote those down right away. I'm also in a place professionally where the immediate next step feels known and evident which means To Dos to arrived without much effort.

Even with knowing my direction in the short-term, it was helpful to gather additional thoughts as I made my way through the Review of last year. It became evident that some themes from last year will continue into this year. It's impossible to keep intentions and goals, as loosely as that can be defined, contained to a calendar year—so why force that?

In this section I collected a list of process goals and intentions, ranging from the general to the specific. I also summarized my direction with a Moving Toward framework of fast, medium, and slow: categories of speed denoting the intensity with which I'm intending to make the outcome occur. Each category had a single outcome as a means of providing focus, though I don't see any reason not to put more than one if it feels right. 


This step was about identifying starting points by asking "Where am I?"

It was an honest assessment of where I am as compared to where I'm going (the To section above). 

There were a few readily available thoughts I placed under a header of "Obvious." Some thoughts are just that. 

It was also useful to ask: What do I like about where I am? And: What do I like about what I'm doing? The opposite of these questions also were useful. I suspect the answers will help express personal values when I'm making important decisions in the coming year.

Yet the best question I've discovered, in terms of identifying present state, comes from Aaron Dignan: "What's stopping me from doing my best work?" 

Is it my organization? My job specifically? My boss? Me? It was important for me to think deeply about the answers and identify barriers in an effort to navigate them.


To close the gap between To and From, I spent time reflecting on the question "How can I help myself get there?" It was brainstorming in a way; although at least for this reviewing and planning session, my target was the practical and pragmatic. 

My professional goals are concrete at the moment. That made it easier to identify next steps. I don't suspect that to always be the case. More time in this section is likely required when the professional future is foggier. 

The ideas that were expressed in this section—for the most part—had been rattling around in my head for the past month or so, though concentration on the question did provide additional opportunities not yet considered. It was helpful to put them to paper, especially in consideration of the final step of this process.

What Now

Finally: the actions to make it happen. 

I started by just writing intentions. Most of them are process goals (and those that are outcome goals are within my power to make happen).

Then I used a categorization method of 30/90/365 days for actions to take and projects to deliver in the next month, quarter, and for the year. 

This process gave me the opportunity to make decisions about various possibilities I'd been considering. Projects and ideas always hold the potential to move in different directions and, at times, those options have prevented me from moving in any direction. This exercise naturally forced priority clarification. 

Particularly important to me was identifying professional skills I wanted to improve because of my recent interest in skill development through practice at work. It was easy to identify three.

Everything I had come up with was naturally summarized in five intentions for the year, none of them SMART goals, for which I'll be able to measure my progress for the year. 

I also wrote a one-sentence theme for the year. That, too, came naturally and was almost the final addition to this section. It was something I built into rather than cascaded down from. 

Finally, finally: Although I didn't do this, I believe a Stop/Start/Continue exercise could be useful in the future. What are task/behaviors/actions you want to Stop, Start, and Continue?

What comes next

Revisiting the What Now section is important in making this exercise action-oriented as opposed to a useful but ultimately useless exercise.

I created an Evernote note with the information from the What Now section as to make it easy to review. I plan to do that in my weekly reviews (20 minutes every Friday), which I've been doing for the last three months, and includes more than just reviewing my thoughts from this exercise. 

As a result of completing this (Personal) Career Reviewing and Planning, I will start monthly and quarterly reviews to revisit my progress toward the intentions and adjust them against my worked experience. Adjustments are inevitable. 

I'm interested in including other people connected to my professional future in this process. I'll see how that develops. There's a lot to think about before approaching someone (boss, mentor, confidant, friend, etc.) with an ask related to this process. Too hot to handle this time around.

I anticipate this exercise to get easier and better with additional iterations. Just the act of weekly and quarterly reviews will provide more information for which to review a previous period of time. 

Ultimately, I found the exercise to be helpful and valuable. And its utility will increase with additional reviewing and planning.

Concluding thoughts

I find it unwise to put our career development in the hands of anyone other than ourselves, even those who are obvious supporters. No one has as much interest in our careers than us.

Others can only assist. Our careers are us things. Only we know where we're going. Or want to go. Or have the ability to figure it out. 

If career development is important to you, then take stock of your situation from time to time and adjust accordingly. 

For most of us most of the time: there's no greater opportunity to steer your career in your preferred direction than with the responsibilities of the job you're doing now.

And beginning with a career reviewing and planning session is as good of a start as any.

Through The Work is a talent development studio for healthcare leadership embracing The Transforming—the always-happening, always-unfolding state of change in your job ... and using it to make more of the change you know should be happening, happen.

The Transforming is the most important professional opportunity of our careers—one that will lead to new job opportunities, real change, and a transformed industry for all of us and everyone else.

My name is Drew Weilage and I work in healthcare, too. At Through The Work, I assist people like you with the skills, attitudes, and points-of-view to propel your professional success. It's personal training for a transforming world of work.

Oh, and pep talks! Get a pep talk when you need one: big day, bad day, or any day at all. Text me at 646-450-2465 or send me a note.

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