Backcast Your Future

You’re planning for a new year. Or quarter. Or project. Woohoo! It’s time to start thinking about all of the things you want to do—your goals, your aspirations, your metrics for success. You’re on it.

Maybe you use a simple list to track your goals. Or use a system like Kanban or OKRs.

If you’re lucky, you file your list in your head or put it up on your wall or into a doc or project management software, make it all happen. And at the end of the next year, quarter, or project, you reflect on how awesome you are for reaching your goals.

And if you’re like me or most of the founders, executives, and teams that I work with , you’ll create your goals, forget about said goals. Or curse those dreaded OKRs because it’s too hard to figure out and give up. Or you let said goals haunt you like a beating heart beneath your floorboards every waking hour for the rest of your year only to get to the end of the year feeling like a failure.

Thump, thump. Thump, thump.

I love goals. And lists. I’m the type of person who has a Kanban board for everything—work, life (yes, my partner and I planned our wedding using Trello). I also love more complicated goalsetting and accountability systems like OKRs (more on that below).

The problem about all of these systems is that they’re not as effective if you’re not first clear on where you’re going and how.

What most goal systems lack is a clear vision. And that…is a story. It’s a story that will excite you, inspire you, and propel you and everyone you work with forward over the next year…and beyond.

If you want to hit the ground running next year, quarter, or project put down your goals.

Write your story first.

For some of you, thinking in stories and using stories to drive grand visions of what you want to create and accomplish comes naturally. Take for example Walt Disney, Steve Jobs, and Dolly Parton (one of my personal leadership and business heroes—more on that another time)…all were and are masters of having a clear story-driven visions of where they were and are going.

For the rest of us, creating story-driven visions to drive you forward can be easily learned.

What you need

To write this story, all you need is a, pen, paper (or download a free Backcasting Worksheet 👇), and ideally another human to share it with. I would say that you also need an imagination, but you don’t. You already have this story in your head. This is an exercise to get it out of your head and onto a piece of paper.

Start with the ending

As many writers know, one excellent way to write a story is to start with the ending. Doing so gives the rest of your plot a focus and a trajectory. And it helps you, the writer, focus and align everything in the story towards something. Real life is much the same. If you start with your ending and work your way back, your story will write itself. Then bringing it to life becomes the easy part.

Choose your Timeframe

Make sure you’re clear about your time frame. I find it easiest to do this exercise at the beginning of a new year (or right before) and to think a year out, possibly 18 months if you want to think even bigger, but you can do it at any time. What’s important is that you keep you don’t limit your time frame to a short period. Doing so will keep your thinking myopic and results not as exciting. If you want to plan out anything less than a year, that’s fine. I still recommend thinking a year in advance and then working your way back so that you’re thinking big picture enough to make your goals lofty enough to drive you.

Map your journey

Close your eyes. Imagine that you’re a year out into the future reflecting on your last year. Answer each of the following questions on a piece of paper (or download a free Backcasting Worksheet and use that 👇) in past tense, first person.

Take no more than 2 minutes per question. It works better when you don’t overthink it.

If you’re doing this with a partner, make sure to write all of your answers before sharing your complete story with the other person. Sharing pieces too soon could end up with your vision being edited, muddled, or diluted, which is not what you’re going for.

1. What did you accomplish?
What did you do? What did you accomplish? Go with whatever comes to you, good or bad. If it helps, I like to use a technique that Benjamin Zander writes about in his book The Art of Possibility: give yourself an A. As he found with his students and as I find with my leadership coaching clients, simply imagining that you will succeed at something makes it much more likely that you actually will succeed. So…you had an incredible year. What happened? What did it look like?

Last [time period/project], I…

2. What was initially standing in between where you were and where you wanted to go?
What was in that initial gap or chasm between where you were at the beginning and at the end? This could be skills that you didn’t have, people you needed to build alliances with, personalities, problems, tasks, anything.

3. What did you do to make things happen and move forward?
What actions did you take, skills did you learn, or behaviors did you adopt?

4. And now, the fun part…What challenges did you face along your journey?
Let’s add some tension to your story—it makes all stories better and will improve yours, as well. Still imagining that you are a in the future, ask yourself: what challenges did you face? What did or could have gotten in your way? Life isn’t always easy (and if it is, you’re probably not challenging yourself enough). What obstacles presented themselves? Inside yourself? Other people? Logistical? Your team? Organization? Home? Family? Be honest here. As screenwriter Robert McKee (who taught much of Hollywood how to write screenplays and who I used as inspiration for my book on story driven product development, The User’s Journey) likes to say—and I’m paraphrasing here: make it hurt!

It’s important to not get into solution mode at this point. Don’t identify how you overcame anything. Just go deep into your darkest fears. It’s much easier to face these fears on paper before they happen in real life along your journey.

It wasn’t always easy…

5. How did you overcome your challenges?
Now you can get into solution mode. Identify how you either overcame your challenges or accepted them and moved on. What did you do? What superpowers did you use? What superfriends did you involve?

But I…

6. How will you celebrate?
Yay! Now you’re at the best—and most difficult—part. It’s been quite a year. You accomplished a lot. How will you celebrate? As I’ve written about before, celebrating is a key ingredient to successful habit formation as well as essential to giving any experience full closure so that you can build energy for what’s next. And it’s fun. So…how will you celebrate?

Put it all together, say it out loud

When you’re done, put it all together and share your full story with someone you trust. Sharing your story with another person will help you check it for loftiness, integrity, gaps, and missed opportunities. It will also take it from feeling like just an exercise to something that feels more real…and ultimately attainable. Don’t ask the other person to judge your story—instead invite them to ask you tough questions so that you can clarify it for them.

Whether or not you’re doing this alone, feel free to keep a copy of your story on your desk or wall to guide you. Or put it in an envelope and open it in a year and see how it surprises you. It should look something like this:

Last [time period], I/we….

I/we had some hurdles to get over and gaps to fill...

So, I/we…

It wasn’t always easy…

But I/we…

To celebrate, I/we will…

Reflect

Now that you’ve put this all on paper and said it out loud, how do you feel? Excited? Scared? What else? All of those feelings are good for you. Unlike the feelings you get when you look at a non-story-driven do do list (dread is a common one), these feelings will fuel you on your journey and enable you to ask for help or pivot when necessary.

If you don’t have any feelings about your story, then you’re not thinking big enough. But I have yet to see that happen.

Now what?

Plan your journey

Now that you’ve written your story, you’re undoubtedly building energy for bringing it to life. What do you need to do to make this happen? Who do you need to bring along your journey? However you normally plan, whether it be a Kanban board, OKRs, roadmaps, and whatever tools you use whether they be spreadsheets, Trello, calendars, gantt charts, post-it notes, or a combination or all of the above, do whatever you already to make things happen. Then make your story real.

However you decide to go about and make this all happen, it’s important to break your year up into quarters and then weeks. This makes an otherwise large scope of work manageable and more easily iterated on as you head out on your journey and experiment and learn. If you don’t do that, you’re likely to return to your story a year from now only to find that you never did anything with it.

Chunk. It. Out. As screenwriters know, breaking experiences down into little pieces before you put them back together again makes them better.

Check in with yourself. Re-write and iterate your story as you live and learn. And also…

Find an accountability buddy (or buddies)

I work with an executive coach so that I can keep my business running, hold myself accountable, and get unstuck quickly as I grow my business (and myself). When I was working full time, in-house, I worked with a leadership coach to do the same. But I’ve also found that having other accountability buddies outside of the coach-client relationship to be essential to my progress.

For example, I’ve been doing personal OKRs with my good friends, Christina Wodtke and Livia Labate, for many years. We do this over email and occasionally on a Zoom call or in person if we’re in the same city. I also have created a network of accountability buddies that were initially there to help me write my book on using storytelling for successful product development (the people development version of this is coming - that’s in my story for next year :) and have over time become a trusted advisory board of good friends and mentors. It’s super easy to do. And it’s an important ingredient you need to make this all happen.

A story is just a story until you tell it to other people and engage their help in making it real.

So…what’s your story? What do you want it to be?