I’m at a major crossroads in my career, and not one that looks like I expected it to just a few days ago. So, I ask myself an important question in this first post of two on Career Planning.

It’s a question that comes up all too often, and that there’s not much guidance for. Not “how do I break in,” or “how can I do a better job,” but the much more basic “now what?”

It’s a place I have found myself many times over more than two decades, but to be honest I thought I was done asking it for a while. When I took a full-time staff position with Paizo, my expectation was that I’d be there at least a decade. But you can’t always predict what opportunities come along (or how they’ll turn out), and you need to analyze them based on your current situation, not your best guess from 5 years ago.

Sometimes you just need to take stock and see if your current, stable situation is doing what you need it to, or if improvements could be made. Sometimes you move across the country because your spouse got an amazing job that ceases to exist after 90 days with almost no warning.

So, my Paizo job made the “now what” question irrelevant only on the macro scale. I still needed to have a plan for growth within Paizo (and becoming Starfinder Design Lead was a huge step for me in that regard), and I had to keep an eye on what I was doing as side-gigs (which is one reason I had to shuffle those so often–side gigs must be treated with respect, but they can’t take so much effort they damage your performance on your main career path), but in general I knew where the next set of paychecks was coming from, and who I was going to be doing most of my work for over the next 6 months, and where I would be sitting my butt most often.

I do not regret deciding my family’s needs were no longer in good alignment with Paizo’s opportunities for me, though I am going to miss not only the stability it afforded, but also the friends I have made and the amazing coworkers I have learned from and grown with. And, obviously, I didn’t expect my move to turn out the way it did and would have handled things differently if I’d thought this result was possible in this timeframe. But the fact is I am in Indiana now, and while I expect Paizo to continue to be part of my career for the foreseeable future, that situation is a freelance relationship rather than a regular paycheck.

I moved without a full-time situation preplanned for myself, and the stable job I thought would remove the pressure of needing to spin up my career quickly has turned to vapor. So I come to a place creative careers often do.

I have to ask myself, “Now what?”

I’ve done this before, of course. When I was laid off from Wizards of the Coast in 2001. When 3.5 came out, and 4e, and Pathfinder 1st ed. Both when I joined up with and then was bought out from Super Genius Games. When I was offered a regular gig doing Freeport for Green Ronin, and when I left that. When I started Rogue Genius Games, and became involved with Rite Publishing. Each of those moments came just before, or just after, that crucial questions about what’s next.

So, how do you answer that question? It takes some analysis, some planning, and some guesswork.

1. Process Your New Reality

Ideally your new reality is what you were hoping for, such as when I got a full-time job with Paizo. I had that rarest of unicorns — a full-time job (with benefits) in the game industry. But even in that case, I should have taken more time to settle into that new position, after 13 years of full-time freelancing, before I took on any additional projects. I thought that since I knew how long it takes me to write and produce game content, and I knew how much of that Paizo expected from me, I knew what my new reality was like. But there’s a big difference between being a freelancer and going to an office 5 days a week, and while I’d held a staff job before, more than a decade of changes in technology and best practices, and working for a different company, meant I wasn’t as prepared as I thought.

I adjusted, and it was fine. But it would have been better if I had gotten a feel for things first, and considered how to augment that situation afterwards.

However, if your new reality is caused by sudden, unexpected, terrible changes of circumstance, processing it may have a very different set of needs. If you have had the death of a partner or colleague, gotten laid off or fired, had a license pulled, or otherwise experienced a swift and unforeseen major setback, you have some emotional needs you need to deal with before you make big plans.

You can’t rush this. It’s going to take the time it takes, and that’s that. However, you can set some boundaries and expectations for yourself. I recommend giving yourself at least a few days, but also to maintain your route work and duties. Of course I am a depressive introvert, so I need to take specific steps to make sure my mental health is cared for, and I can’t give other folks specific advice how to do that.

My point is, take care of yourself and don’t make any huge decisions you don’t have to in the first few days of a big, negative change. And if you need more help than that, get it. Huge life changes are tough, and the most important part of your career is you.

2. Review

For me the first thing I do when I am at a crossroads is look backward.

It can be hard to properly assess projects and jobs while you are doing them. Since hindsight is supposed to be 20/20, the moment when you aren’t sure what to do next is a great time to look back over the past few years, and analyze what things went well, and which ones didn’t. This isn’t just about money, or ease of work, or satisfaction, though all those things should be considered. I also like to ask myself, if I knew then what I know now, would I still do the same things I did in the past few years.

I consider this a post-mortem, rather than a time to kick myself or dig up regrets. Often there was no way to know what unrelated things might make a great opportunity turn out terribly, or save a disaster from being much of a problem. But often there were subtle signs I could have paid more attention to, and thinking about what they might be helps me catch them in the future. I also want to analyze what I learned, what I enjoyed, what I made good money on… and what I feel burned out about, what opportunities I missed, and what I feel like has begun to put me in a rut either creatively, or in my career.

For example, I was between projects in 2012/2013, when Lou Agresta asked me if I wanted to write for the Heart of the Razor Adventure anthology for Razor Coast. Now, writing adventures is more work for me than the same word count of worldbuilding or rules expansion, so I often skip it. But, I realized I hadn’t written an adventure in years, and a number of people in the industry had begin to refer to me as a “rules guy.” So I accepted, to change up  my perception in the industry, and get myself out of a rut. (And it won an ENnie, and within a year of it coming out Paizo was asking me what adventure I had done recently I was most proud of… and I had something great to point to!)

On the other hand, right NOW I have written two adventures in the past 3 years (one yet to be released), and I don’t feel like it’s a good time for me to be working on slower products that aren’t (currently) an underserved area of my career. Different point in my life, different answer.

In a week we’ll look at Part Two, where I discussing looking forward, and making plans.

Part of My Plan is Patreon
Heya folks–I am back to being a full-time freelancer. Which means, ever word I write has to justify itself in time taken vs. benefit to my freelance career and/or money made.
So if you found any of this useful and you’d like to support the creation of more such content, check out my Patreon!

Just a couple of dollars a month from each of you will make a huge difference.