How do you think about your own career planning?

chrislema-face

I've been asked a lot recently about my next steps and what I'm pursuing. As I've answered the questions, I've seen a lot of eyebrows raise. I think it's mostly because of how I think about career planning.

The best route to the most value

Since leaving Crowd Favorite, no question has been asked of me more than “What's next?” and with that, other sentiments have quickly been shared with it:

  • I've always seen you as an entrepreneur
  • I bet you're thrilled to be your own boss
  • I can't even imagine the number of ideas you have now that you're on your own

None of these are bad statements. None of them are wrong. I am an entrepreneur. I like managing my own time. And I always have a lot of ideas.

But none of them are perfectly accurate either. While I have several ideas that I'm exploring on my own, I'm also talking to other companies about what they're up to. You know why?

Because I'm constantly looking for the best route to the most value.

How do you define the best job ever?

Before I explain what I mean by the best route to the most value, let's first talk about how you define the best job ever?

  • Is it the job that gives you the most money?
  • Is it the job that gives you the most freedom?
  • Is it the job that feels the easiest to do?
  • Is it the job that makes you feel the most important?
  • Or is it some mix of these?

Have you ever bought a Swiss Army Knife?

When I was 10 or 11, I went camping with my family and we met another family with kids our age. One of the boys had a swiss army knife. It was so cool. We used the scissors to cut our kite string. We used the magnifying glass to start a (controlled) fire in the fire pit. We used the phillips screw driver to tighten a bolt on their bicycle. On it went.

So when I came home, I wanted one.

There was only one problem. After buying it, I had nothing to use it on. I spent time pulling the blade out and closing it back up. But that was it. In my normal home and school context, there were no places for me to use thatSwiss Army Knife. It was a waste of my money.

Know why I'm telling you my story of the Swiss Army Knife?

Because it is the main paradigm of how I think about career planning.

The best job ever, for me, is one where each of my skills, interests, and experiences combine to deliver the most value possible.

If I take a job where only 2/3 of my skills and experiences are used, it's not a route to the best/most value, is it? It's like a Swiss Army Knife that's only needed for the scissors.

Tools to help you know more about yourself

This is partly why the idea of working for myself has never been at the top of my list. I have a lot of cool ideas. But most of my value is delivered in a context where someone else has a grand vision but is struggling to achieve what they want.

Their impasse creates an opportunity for me to help them, and in so doing, bring my talents and experience into a place where it can be exploited (by the company) for its own gain.

Of course, providing the bridge can also be a wonderful feeling of helping people. If that's something you dig.

But that brings us back to what motivates you. What you care most about.

And that's where I find some tools are really helpful. For me I use the StrengthFinder and the Kolbe A Index.

The more you know yourself, the better you're able to define the right context where you provide the missing piece.

And when you deliver unique value in a context where it's missing, you can generate the most impact—which often leads to positions that pay better and are more enjoyable.

My career is an asset with expected returns

I'll be honest—my wife expects that my salaries will increase over time, not shrink. Over the years we've been strategic about taking pay cuts where it's been appropriate. But all in all, my experience should play a role in my worth, in the corporate world. And so, to that end, my wife expects that each year I work, as I develop more skill and expertise, it should have some benefit to our family.

She's a smart woman—my wife.

Both of us look at my career as a financial instrument. Every job is an investment that will either add worth and value or reduce it. And our job is to monitor the financial return from the career and make sure it's doing what we want it to.

This, of course, takes me back to my Swiss Army Knife illustration—my goal is to step into opportunities where my whole self is being leveraged. It's where the most value is delivered.

Keys to my career success so far

Every time I've moved between jobs I've had to answer some key questions for myself:

  1. What have I learned to date that can help another organization?
  2. Where have I had consistent success that can help another organization?
  3. What have I enjoyed most in this last effort?
  4. What have I enjoyed the least in this last effort?
  5. What do I want to learn next?

That last question has often been the deciding factor, not salary, in helping me decide what I'm going to do next.

I can't tell you how many opportunities I've passed up because, while they were great, didn't create an opportunity for me to bring #2 with me into a new role. I also can't tell you how many times a lack of clarity around #5 likely meant a poor fit.

And this is why you soon realize that just because you can do something doesn't mean you should do it.

As I embark on this next journey, these are the questions I'm asking. And the story of the Swiss Army Knife provides the core guidance on how I think about opportunities.

If you want to talk about your next steps, I'm always available via Clarity.

About Chris Lema

Chris Lema has been working with WordPress since 2005. Over the years he's been a blogger, a speaker at WordCamps, a coach for WordPress product companies, and the founder of the conference for WordPress business owners, called CaboPress. Today he's the VP of Products at Liquid Web, where he manages the world's first managed platform for WooCommerce stores.

Chris Lema

Chris Lema has been working with WordPress since 2005. Over the years he's been a blogger, a speaker at WordCamps, a coach for WordPress product companies, and the founder of the conference for WordPress business owners, called CaboPress. Today he's the VP of Products at Liquid Web, where he manages the world's first managed platform for WooCommerce stores.

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