I’m at a major crossroads in my career, and not one that looks like I expected it to just a few weeks ago. So, I ask myself an important question in this second post of two on Career Planning (you can read Part One here).

We covered step 1, process your new reality, and step 2, review. So that brings us to:

3. Look Forward

I often open advice sessions with other people with “Where do you want to be in two years?” It is, for me, a perfect amount of time. Far enough ahead that you can discount immediate but temporary inconveniences such as a sprained ankle or massive looming deadline, close enough that you can visualize the time between now and then. For other people different timeframes might make more sense, but my 5-year plans very rarely go anything like as planned, and when looking forward 6 months or less I am often skewed towards immediate issues that aren’t necessarily representative of what I am going to face in general.

So, where do *I* want to be in 2 years? As I make a list of those things I find, unsurprisingly, that a lot of them involve money.

And money involves a budget.

Budgeting isn’t any fun, but it’s a crucial part of a freelance career. If I am going to successfully reach any of my goals, many of which involve things like buying a house and paying off student loans, I have to be able to account for more than just my immediate bills. Freelancing if often filled with feast-or-famine incomes, where you get paid for several things over the course of 2-3 weeks, and then nothing to speak of over 2-3 months. It’s important to do more than just cover the rent and groceries. You need to be able to sock away for emergencies, long-term needs, even retirement.

That just isn’t likely to happen without a budget.

You also need to consider what skills and contacts you should improve to meet your two-year goal, whatever it is. Do you want to have a published novel? Then you better both be writing is NOW, and talking to anyone you can about how to get it published. Want to have your own game company? I recommend working as an assistant to someone else who has one, so you can learn the ins and outs by watching and helping, before you have to figure it out by doing.

The review is also the time to have an honest talk with yourself about what your weaknesses are. Are you bad at adventure writing? You can either plan to just avoid having to do that, or to get better at it, but you won’t know that’s something to take into account unless you are aware of it as a weakness.

You also need to be realistic about your strengths and weaknesses. Impostor syndrome is rife in this industry… as is the Dunning–Kruger effect. Combating those in yourself is tricky–it’s always easier to see bias in others rather than yourself. I recommend both trying to describe how you would expect someone who gets the kind of work and responses you do objectively to see at least ho you are seen by others, and to ask people you trust who are more successful than you to give you their honest assessment of your pros and cons.

The whole point here is to be able to look forward from a grounded place of information about yourself. You don’t need to beat yourself up or gild your own laurels, but if you don’t have a rough grasp of where you ARE in your career, it’s very tough to plan a course forward.

It may be worth considering what kinds of jobs you have already done and think about which ones you’d like to do more of. My article “Developer? Designer? Who is the What Now?” may be helpful for thinking about different kinds of tasks within the writer end of the TTRPG industry. If you are more focused on art, editing, or business and planning, those are still useful distinctions to know, but you should consider what kinds of sub-divisions your own career has revealed.

Try to boil all your “looking forward” ideas in 3-5 bullet-points of 1-2 sentences each. If two bullet points look similar, see if you can blend them into one slightly broader bullet point.

My first run at that list of ideas looked like this. I offer it only as an example — your list should definitely look different, based on where your career is, and where you want it to go.

*Make enough money to cover more than just the necessities, including health care, buying a house, retirement planning, and the occasional vacation.
*Expand my professional skillset to be able to take advantage of any text-based or business-related aspect of the game industry, including working in different game systems,  being a manager, and overseeing licenses.
*Build my online and social media presence to make it easier to directly reach fans and potential employers, possibly including doing more videos, streaming games, and redesigning my website to be more modern.
*Build income streams separate from per-word writing, possibly including growing RGG, doing more royalty-based projects, and patron support (such as my Patreon, which supports this blog and gives me time to write things like this article-Join Now!)

Now that you have an idea of where you are, and where you want to go, it’s time to:

4. Make Plans

This is going to be one of the vaguest sections of this article, because your previous steps should already be leading you to a different destination than mine–possibly a different destination than I could even think of. So making plans to get you from where you are to where you want to go in your career should look very different than getting me where I want to go. But I do think there’s some high-level advice that can still be broadly useful for making plans.

The first is: schedule your time, then fill it.

It’s very temping to do this the other-way ’round: to find things to do, and then go looking for time to get it done in. And at a casual or hobby level, that’s fine. If you mostly want to just post a few articles on free sites and occasionally get paid for a bit of work that drops in your lap, you probably can just schedule things as they come along. There’s nothing wrong with that by the way–I strongly suspect more TTRPG words get written each year by people who enjoy it as a hobby than those who see it as a side-gig or want it to be a full-time career.

But in my experience, if you want to step beyond that, you’ll eventually need to do the hard work of carving out time from everything else, and then filling that time. If you don’t have enough work to fill the time you set aside? Then it’s time to use the spare time to work on some RPG Pitches. If you don’t have enough time set aside to do all the work you’ve gotten?

Then it’s time to take a hard look at whether you need to set aside more time, write faster, or work less. For any of those answers, you may end up trying to Survive on 5 Cents/Word (or Worse). Good luck, sincerely.

As you set aside time, make sure some of it is saved for making contacts, pitches, and seeking better opportunities, and that includes opportunities for self-improvement. Work and learning opportunities may just fall into your lap sometimes, but there’s almost always more work you can get if you go hunting for it, and that often includes better options. If you want regular income, for example, you may need a regular gig writing articles, or running a Patreon, or being a part-time contract employee of a game company. Some of those things you can set up yourself, but that takes time too.

This is often the hardest part of planning a career. While there are now formal education opportunities to get involved in gaming (and not all of them are focused on computer games, and many of the skills are fungible even so), nearly everything I know about being a game industry professional came from working with people smarter, more talented, and more experienced than I was. My time on-staff at Wizards of the Coast, Green Ronin, and Paizo taught me there is something I can learn from everybody in the industry, even people with much less experience than me. I needed to be open to the opportunities to learn from them, and that often required I take the time to consider why they wanted to do something differently than I planned to. Yes, deadlines are often tight and there is a time and a place to be a strong advocate for your own vision and experience, but never let that cheat you out of a chance to learn a new resource, skillset, hard-learned lesson, or even just a new point of view.

So, look not only at what work you can do, but what doing that work may mean in terms of advancing your career. There are people in this industry I will always work with if I can, because I always learn from them. I try to challenge myself to take on things that put me out of my comfort zone, and set aside extra time to get those uncomfortable things done.

Sometimes that means an opportunity doesn’t pan out, and that can be especially painful if you gave up something stable for it, and/or were depending on it for a major part of your income. It’s good to note these things (like in future rounds of processing and reviewing your new reality), but it’s not a reason to not try new things. You’ll need to balance potential risk with possible reward, and I can’t tell you how much risk to take for what reward level. Just be realistic with yourself, and never take a risk you can’t survive going badly if you don’t have to.

So, with those steps in mind, what am I looking at for plans to carry my career forward? I’m not going to go into ever deep detail, for obvious reasons, but I think it’d be a bit of a cheat not to wrap this up with some concrete examples of where this process has lead me. So:

I’m the Fantasy AGE developer for Green Ronin. This is a part-time contract position, working with some of the smartest and most experienced people in the TTRPG industry, and it’s a stable source of some income every month. That hits a number of my goals, from working with new game systems to being around people who can help me be better at a wide range of TTRPG industry tasks. I’ll be looking for more similar opportunities, but I am super-stoked at making this part of my long-term success.

I’m focusing more on my Patreon, including posting a new goal promising videos and bonus content if it hits $1500/month. It was, to be honest, extremely scary for me to consider a $1500 goal, but my $700+ goal having been met, I have to take that risk. And if it turns out the public doesn’t want what I am offering for that level of patronage? I’ll re-assess, and try again. I see this as both a way to seek semi-regular income to help meet my financial goals, and to force me to learn and offer new things to stay connected and relevant to the ever-changing TTRPG market.

I’m setting aside more time for Rogue Genius Games. There are types of projects I have never dared tackle with my own little gaming company, and forcing myself to try them is another way to exp[and my skillset. And of course writing more of my own products also means having more royalty-based projects, which is a good way to build income streams that aren’t exclusively one-time per-word money.

Fiction. I am going to do it, this time. I am terrified.

More traditional freelance. I need the money in the short-term, and the contacts in the long-term. So I am throwing my doors open to new publishers, new projects, and new game systems. Time to prove I am more than a d20 game mechanic guy.

So, for the moment, in broad strokes, that’s it for me. I’ll compare my results to my needs and plans (especially my income vs my budget) every 90 days (and more frequently if things are obviously out of whack). And every 6 months or so, it’ll be time to do the whole process again — process, review, look forward, and plan.

It’s a never-ending process, but that’s okay. I never plan to stop having a career, so I can afford to take time to adjust and rethink as needed.

In fact, I can’t afford not to.

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.