How to experiment bravely to make a successful career change

Ready. Aim. Fire! This is how we should approach our Escape, right? Make sure you’re ready. Carefully prepare until you know you’re ready. Then (and only then) start moving!

It’s easy to get stuck in our heads around the introspection, theory and navel gazing that comes along with making a career transition. Of course, it’s important to know who you are, what matters to you, and what you want to help you move in a direction that’s right for you.

But at some point (and this point comes a lot sooner than we want it to) we must start acting. We must start moving, doing, putting ourselves out there and engaging with the world.

This is the hard part, but it’s where the real magic happens.

People who stage successful Escapes do so by constantly acting, testing, stepping their way here. They do it by approaching their escape as a series of small projects rather than gigantic leaps. They do it by acting like a scientist and viewing each small move forward as an experiment rather than a lifelong be-all, end-all decision. They do it before they feel 100% ready and without having it all figured out. For destinations unknown like career change, Ready, Aim, Fire! doesn’t work.

The foolproof ten-step plan won’t get us there. Starting only once you’re ready is a surefire way to never begin.

The essence of Experimenting Bravely is this: Act first. Reflect later.

It asks that you pick a direction to test out. Actions need not be massive leaps. Instead think small, deliberate steps forward. Hell, half steps if you must. This isn’t about making a decision forever; it’s about making small decisions to help you get clearer on your potential direction.

Up until this point, you’ve embraced the many possibilities, curiosities and ideas for your future direction. By reading this article, your task is to narrow down your focus and pick a direction of travel.

Read on to discover how to experiment bravely and test your way into a new direction that’s right for you.

experiment bravely

Embrace a Project Mindset 

Plotting your escape can feel like trying to shift a giant glacier. It’s hard enough to figure out where you want to go, let alone the best way to get there, and where to start. If you get too caught up on trying to shift a glacier, you risk never starting. Instead, try viewing your Escape as a series of tiny steps. Or better yet, a series of self-contained projects.

Projects are temporary. Projects are short-term. Projects have a self-contained goal. Projects can be fun. The outcome of a project need not be tied to your ego and your self-worth. The goal of a project is to inch one step closer in your escape.

Examples of projects might be: 

  • Lead a “women in social enterprise” meetup for 6 weeks.
  • Journal 500 words every morning for the next 30 days.
  • Make a batch of your baked goods (or fashion accessory or whatever else) and commit to selling it at 5 different market stalls.
  • Try coaching a handful of friends or colleagues for free.
  • Launch a public art project to explore a social experiment you’re curious about.
  • Start a book club to read and discuss books on entrepreneurship.

The essence of the project-mindset is: “I’m going to try this X thing out for the next Y weeks and see what happens.” Commit to a set amount of time (6 weeks), a certain milestone (writing 5 blog posts), or another metric (get 3 paying customers).

Just because you’re viewing this through the lens of a project doesn’t mean you do it half-heartedly. You obviously must still care deeply about the project and you must give yourself enough time to learn from it. It may or may not work out. That doesn’t matter. What matters is that you’re trying something out and learning from it.

Make Little Bets

Another way to embrace the project mindset is to apply the theory of “little bets” in your potential future directions. Consider the series of projects you take on as a long string of little bets designed to learn more about your future direction.

little betsThe concept of little bets comes from Peter Sims, author of Little Bets: How breakthrough ideas emerge from small discoveries. As Sims studied various innovators from Steve Jobs to Chris Rock and innovative companies from Pixar to Amazon, he found their approaches embraced a similar quality: they made little bets until they hit upon something that worked:

“Rather than believing they have to start with a big idea or plan out a whole project in advance…they make a methodical series of little bets about what might be a good direction, learning critical information from lots of little failures and from small but significant wins” 

The same goes for our pursuit of more fulfilling work and the possibilities we’re testing out. In his book So Good They Can’t Ignore You, Cal Newport applies the theory of Little Bets to his study of how people end up doing work they love in service of a mission they care deeply about:

so good they can't ignore you“…great missions are transformed into great successes as the result of using small and achievable projects––little bets––to explore concrete possibilities surrounding a compelling idea.” 

Newport goes on to say: “The important thing about little bets is that they’re bite-sized. You try one. It takes a few months at most. It either succeeds or fails, but either way you get important feedback to guide your next steps. This approach stands in contrast to the idea of choosing a bold plan and making one big bet on its success.” 

While your little bets or projects may just help you learn more about your direction, they could turn into something much bigger than intended. Sam Altman, president of tech accelerator Y Combinator (which has birthed companies like Airbnb, Dropbox, and over 800 others) says about the project-mindset:

“The best companies start out with ideas that don’t sound very good. They start out as projects, and in fact sometimes they sound so inconsequential the founders wouldn’t let themselves work on them if they had to defend them as a company.

Google and Yahoo started as grad students’ projects. Facebook was a project Zuckerberg built while he was a sophomore in college. Twitter was a side project that started with a single engineer inside a company doing something totally different.

Airbnb was a side project to make some money to afford rent. They all became companies later. Great companies often start as projects.” 

Your projects may not turn into a full-blown company. But they could likely spiral into something you never could have predicted.

act like a scientist

Act Like a Scientist 

As you experiment bravely, start projects and make little bets, the persona that will best serve you is that of a scientist. A scientist may have a hypothesis and might be hopeful of a certain result, but that’s not her main concern. Her job is to prove or disprove her hypothesis and remain unbiased through the process. She cares most about what she learns from the experiment.

As you complete a new project or conduct a new experiment, you gain a new piece of information to carry with you along the way of your Escape. A successful outcome is not the point. The point is to learn.

Reflect as a scientist would. With every project or experiment, ask yourself:

  • What are you learning?
  • About yourself? About your ideas?
  • About your possibilities and curiosities?
  • About what you enjoy? What you don’t?
  • About what you’re great at? What you’re not so great at?
  • About how the world responds?
  • What are the ingredients of your project that you want to take with you?
  • What components can you discard?
  • How can you use your learnings to conduct a brand new experiment?
  • How does this inform your next small steps?

You might think:

  • What if the project “fails?” 
  • What if I don’t enjoy the project as much as I thought I would? 
  • What if things don’t turn out how I hope? 

Great! You just learned something. Every outcome is a new piece of feedback. As long as you’re learning and keep conducting new experiments, you’re doing it right, regardless of the outcomes. A ‘failed’ outcome is just as informative as a ‘successful’ one.

Each outcome helps to inform you of your next steps and experiments. With each action, you learn something new.

Winston Churchill quote

What Good Action Looks Like 

It’s easy to confuse good action with procrastinating action. When in doubt, remember that good action checks many of these boxes:

  • It interacts with the world (1 person or many people).
  • It’s small enough to be realistically achievable.
  • You want to do it, but it’s uncomfortable (7 out of 10 comfort level)
  • You don’t want to do it, but you’re excited when you think about having done it.
  • There’s a small degree of risk involved or potential for making mistakes.

Feeling stuck and can’t think of good actions? Here are some ideas:

  1. Reach out to your role models/heroes/heroines: Role models are the embodiment of a person or part of a person you hope to grow into. They’re the tangible example of something you aspire to become like. People you admire may embody a trait, a habit, an expertise or a body of work that you respect. Make a list of people you admire. Be clear on why you admire them. Take it one step further and reach out to them. Ask to interview them. You may be surprised who says yes.
  2. Conversational research: Interview someone who is doing what you might want to do. Ask them what their day-to-day is like. Ask them how they got there, what they’ve struggled with, and what their advice would be to someone who’s just starting out.
  3. Shadow someone: Ask to shadow someone who is doing what you might want to do. Witness their day-to-day.
  4. Start and complete a short project: A great way to learn a new skill or finetune a current one is to spearhead a project applies that skill. Three months is a good amount of time to complete a small project.
  5. Attend a meetup: Go to Eventbrite or and search for a topic you care about or community you’re interested in. Introduce yourself and expand your circle.
  6. Start your own meetup: Don’t see something you like on Eventbrite or Start your own!
  7. Introduce yourself in a new way: The next time you go to a party or meetup, practice introducing yourself in new ways. Test out different narratives and styles. When you share what you care about and who you are, you give the right people an opportunity to enter your life.
  8. Unnecessary creation: Create something (a piece of writing, photograph, whole project) for the hell of it. Don’t worry about the objective. Just do it because you want to do it. If there’s someone who helped inspire your creation, share it with them and thank them. They’ll appreciate it.
  9. Do free work: Work on someone else’s project. Take on a microproject. Volunteer your time to help out a startup that is low on resources. Doing free work for someone else can help you learn a new skill, grow a current one and open the door for a future opportunity.

Find a tribe and use It! 

Find a safe space within a group of friends or family to practice hustling and share your new narratives:

  1. What you want to start as a project (at the moment, don’t worry about it being perfect)
  2. What you’re exploring right now.
  3. Your next action.
  4. What you need help with.

Of course, this isn’t something that starts and ends. These are things you’ll need to share often, for many months and years beyond. Treat this like a marathon, not a sprint.

small steps

Think Small Steps over Big Leaps 

The “big leap” is what you see publicised in the media and even at Escape The City. The big leap is sexy. The big leap sells the dream that people who make a drastic change or begin a new venture did it with one single brush of bravery. The big leap is also misleading and largely unhelpful. It can make you feel that your own escape is a daunting distance away from becoming a reality.

The reality is that the big leap is just the tip of the iceberg. If you look at anyone who has successfully Escaped, at the base of their iceberg are a series of little steps, tiny projects, mini-experiments to lead to that almighty big leap. They’ve tested their way into new possibilities. They’ve experimented bravely in a direction they were curious about.

With every little decision, every little project, every little experiment, every little step: you’re learning. Learning about yourself, about the things you like, dislike, about the things that matter to you, about your strengths, interests, gifts and passions.

And when it comes time to make a big decision or take a bigger leap, you’ll be ready because of the steps you’ve already made along the way. You’ll have become more confident in yourself, your abilities, who you are and what you stand for. You’ll be ready because of the little deliberate projects and experiments you’ve been making already.

Make an agreement with yourself that instead of giant leaps, you’ll commit to a series of little steps, projects, experiments and actions. And when the time comes to make a larger leap, you’ll be ready to heed the advice given to a young Native American at his initiation:

“As you go the way of life, you will see a great chasm. Jump. It is not as wide as you think.” 

career change leap

Doing something different with your life and career is hard… but you don’t have to do it alone. If you need help with your Escape and if you are ready to re-take control over your life, consider:

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