Hey, it’s Alvin!

How do you succeed on big, hairy projects with lots of unknowns?

I’m planning to move to a new place later this year. So, a friend of mine raised a concern, “wait, you don’t drive. How are you going to get around?” I shrugged and replied, “I don’t know. I’ll figure it out.” My response probably surprised him. Shouldn’t I have figured that out before I bought the place? Well, I know what my options are. I just haven’t ironed out those details because I don’t need to yet.

That wasn’t always how I approached the unknown.

When I was a kid, I was a meticulous planner. I zealously planned things out in detail years in advance. And I didn’t want to start on big projects unless I knew exactly what to do from start to finish. None of those plans panned out because the world is full of unknowns that are hard to anticipate. And those unknowns can ruin or alter the best plans.

Working as a software developer completely changed how I thought about planning.

Unknowns in Software Development

As I mentioned in Dive 16, software projects are full of unknowns too. So much so, it’s almost impossible to know exactly how much time you’ll need to finish features for complex applications. Software projects have so many unknowns, we often start making software without knowing exactly what the finished product will look like.

For example, let’s say we’re designing a retail website for a client who wants to sell books online. The client has clear requirements on what the website should look like and what features it should have. They’ve also told us that some day they would also like to sell clothes. But we have no details on that at the moment. The plan is to finish the book part of the website, then the client will decide how to proceed.

For those who are new to this process, the uncertainty with the clothing part of the website can feel uncomfortable. We know the website will sell books and clothes, but it feels like we’re missing 50% of the information. It feels like if we could just wait for more information, we’d have more confidence to move forward. It feels like we’re not ready.

In fact, we ARE ready.

We have enough information to build the book part of the website. So, that’s what we should focus on. Meanwhile, we can design and build the website to give us the flexibility to expand towards clothing to minimize future rework.

We don’t want to do any work on the clothing part until the client has some requirements for us, anyway. Because we don’t want to make any wrong assumptions that lead us to waste precious time and effort on something the client doesn’t need.

Starting before you’re ready can be daunting. So, I focus on imminent problems and see how they relate to one another. To do that, I learned to break down the project into bite-size tasks, then prioritize them while respecting their dependencies.

Software development taught me how to move forward despite future unknowns. In doing so, I learned to be more comfortable with uncertainty. This approach has helped me with other creative pursuits.

Unknowns in Book Publishing

In fact, two years ago, I started writing my very first book. In my younger years, I would’ve thought to myself, “I don’t know how to edit or format or market books.” All those unknowns would’ve made me feel like I’m not ready or competent enough, so “why bother starting at all?”

Things are different now. Having done some research on the book publishing process, I knew what the major steps were: write, edit, format, market, sell, etc. I did just enough research to get a high-level sense of the most critical things to be done on each step. Along the way, I identified all the risks that could put the project in jeopardy; for example, getting permissions for references. And I noted the earliest opportunities I had to address those risks.

Knowing all the major milestones on the path to the final product also helps me, because completing each one gives me the satisfaction of being one step closer to the finish line. By the time I started writing, I had a good enough, though still vague, idea of what I needed to do at each step. I knew what my options would be at each stage.

But when I started writing, I focused on writing. I wasn’t worried about the cover, the title, or the format because none of that stuff mattered if I didn’t have enough to write. Those were unknown to me while I was writing. In fact, by the time I finished writing and editing, a theme emerged that never would’ve occurred to me at the start. Had I designed the cover from the start, I would’ve had to change it to match the new theme. Some tasks are meant to be done in a certain order.

This was a life-changing revelation for me: you’ll never feel ready enough to embark on a journey with lots of unknowns. That feeling of unease stems from lower confidence because of the unknowns ahead. By stepping forward, the obstacles ahead become clearer as you close in on your destination. The more steps you take, the more information you gain. Confidence grows.

If I can do it, so can you.

“The longest journey begins with the first step, but it helps to know where your journey will take you. This doesn’t mean you will know every step of the way, because writing is always full of surprises—twists and turns that the author doesn’t expect. That’s part of the fun of writing. But most writers I know have a destination in mind. They know where they want to head even if they can’t tell you exactly how they intend to get there.”

-          Ronald B. Tobias from 20 Master Plots and how to build them

Thanks to this realization, I published my first book ever, The Vanity Trap. It’s how I started making visuals. And it’s why you’re reading this newsletter.

I still haven’t decided how I’ll get around when I move into my new place. But I know my options. I’ll cross that bridge when I get to it.

I hope you enjoyed this dive Below the Surface of readiness. Reply to belowthesurfacetop@gmail.com if you have questions or comments. How do you handle big projects with lots of unknowns? I’d love to hear from you.

Thank you for reading. Have a wonderful day. And I’ll see you in the next one.