So you’ve made time to reflect on your career and have some fresh ideas? Congratulations! Kudos to you for carving out time, wrestling with these difficult questions, and taking a step back to identify patterns and generate new ideas. If this process felt challenging or uncomfortable, that’s very natural. This may be the first time you’ve actively engaged with these types of questions. If you feel like your career has just “happened” to you, taking the time to think intentionally about your next step is a big leap. Critically examining your work history and cultivating an open mindset for the future is no easy feat.

In Herminia Ibarra’s book, Working Identity, she explains, “To bring your ideal next career move into reality, we must test and learn possibilities, rather than predict what might make us happy and execute against that prediction.” It’s not enough to apply logic or research to a job search; we need to actively immerse ourselves in different roles to find out if they fit our preferences. The work you’ve completed helped uncover clues and generate different hypotheses. Developing a hypothesis requires research and careful thought, but in order to prove it, you need to test it. 

Recognize the fear

Testing a career hypothesis can feel like an uncomfortable leap. It’s not uncommon to feel fear around making a change. The longer you’ve traveled on the same trajectory, the scarier it can be to make a pivot. People fall victim to the sunk cost fallacy “when they continue a behavior or endeavor as a  result of previously invested resources (time, money or effort)”. In the face of perceived serious investment, it’s more difficult to objectively weigh the benefits against the drawbacks of making a change. If you have other dependents, like a partner or children, the stakes feel even higher. These fears fuel narratives about who we are and what we ought to do. From this narrow space, it’s hard to experiment with other options because the pressure to “get it right” on the first try feels overwhelming.

Shift your mindset

In order to make a change, we first need to identify and change the stories we tell ourselves. What subconscious rules do you believe about your career and what it must look like? A helpful exercise can be to write down your list of shoulds and then tease out the needs that each should serve. Perhaps you carry a belief that you “should” be a nurse. The underpinning needs underneath that “should” include a need to help people, connect with others, earn financial income, or gain attention and acknowledgment from others. Start to interrogate these shoulds to see if they still serve you or see if there are other possibilities. Are there other ways to meet those underlying needs? During the experimentation process, it’s important to remain open and check in with your gut to get a clearer picture.

Test your career hypotheses

Once you shift your mindset into an open and curious frame, you’re ready to start experimenting. During this discovery phase, you’re using your career road map as a guide, seeking out experiences that help you learn about the realities of a new role, and checking in with yourself to reflect and see if it’s a good fit. Here are a couple of different techniques you can use to gather this information.

Coffee chats

A good way to learn if your understanding of a role matches up with its day to day reality is to speak to a person who currently does it. Reaching out to a personal connection or even cold emailing a person is a common networking practice in tech. However, in order to be successful and respectful of the person’s time, it’s important to be prepared and make a clear, focused ask.

You may find a person you want to speak to when you’re out at an event. Perhaps a friend of a friend works in a role that interests you. Or maybe you absolutely love a certain company and would love to talk to someone who works in your ideal role. Regardless of how you find the person, make sure your ask answers these specific questions:

• Why do you want to talk to that specific person?
• What do you want from them?
• When do you want to meet with them? For how long do you want to meet with them? Give them the option to meet in person or through a video chat platform like Zoom. (Being able to see the person’s facial expressions/body language helps them get to know you better.)

Asking to “pick someone’s brain” or sending a generic note that feels like spam is a surefire way to get no response. If you’re asking someone to share their expertise with you, you need to explain why you admire that person’s work and demonstrate the connection between their work and your interests.

Before you meet with the person, do your homework and generate targeted questions to ask the person. What feels unclear about the role? What would you like to learn more about? What are your most important role characteristics, and does this role fulfill them? Clarify the information you want to learn through this interaction. 

On my website, MegDuffy.com, I created a weekly series called Tech Role Models to highlight the day to day of different roles in tech. Each person receives the same questions, but two folks in the same role may have different average days depending on the company. You can use these questions for inspiration when starting your own list. 

• Tell me a little bit about your career path. What did you study? How did you get to where you are today?
• What attracted you to this role?
• Walk me through a typical day in your role. What activities do you engage in? What types of meetings do you join? When’s lunch?
• What skills/technologies help you succeed?
• Aside from technical skills, what personality traits/characteristics make for an ideal candidate in your role?
• What skills (tech/non-tech) have you improved as a result of working in this role?
• What’s the most fun or creative part of your role?
• What are the biggest challenges you face in this role?
• What teams/individuals do you work with cross-functionally? Can you give an example of a time when you collaborated with another group/individual?
• What’s an area where you’re trying to grow in your role?
• In your role, what metrics define success?

After your conversation, send a thank you note and reflect on your findings. What about what you heard appealed to you? What concerns arose? Did other questions pop up? Give yourself time and space to check in with your gut and gauge your response. 

Project-based learning

Coffee chats with folks in the industry are a great way to learn about roles and identify skills gaps. If you discover that your experience is lacking a key skill set, pursuing project-based learning to fill the gap is a solid next step. Project-based learning doesn’t necessarily mean an absence of theory and principles. Rather, it’s an education model that requires students to apply knowledge to solve a real-world problem. By learning new skills and then rapidly putting them into practice, you’re not only learning by doing, but you’re also learning if you like what you’re doing. Professional development certificates, online courses, and discipline-specific bootcamps are all good ways to gain experience and fill skills gaps. If your company offers a professional development fund, continuing education is a great way to use it.

Side projects

Formal education isn’t the only way to build a portfolio and demonstrate skills. If you want to demonstrate your knowledge or rebrand your career in a different direction, you can start a side project. I used this strategy early in my career when I wanted to move from the non-profit arts world into tech. I started a project where I conducted interviews and wrote articles to demonstrate my writing and digital skills. I also created a newsletter, marketed the site, and tracked my progress in analytics. My readers sent me ideas and feedback, so I constantly tweaked my product and my process. When I went into interviews, I could point to my project and say, “I built that.” 

The format of your side project may depend on the role you seek. If you want to show off your programming skills, build a prototype or contribute to an open source project. Perhaps you’re a designer with a knack for Adobe Illustrator. Record video tutorials to deep dive into specific topics and share your knowledge with others. If you’re trying to break into social media, see if there’s a small business that could use your help. Want to gain management experience outside of the office? Volunteer with an organization you love and ask to supervise a group of volunteers or lead a project. You can write about your experience or have the organization share a testimonial that highlights your new skill set. All these methods help you apply your skills in a new context and build a body of work that demonstrates your skill set to employers. 

Don’t forget: you may be able to build these skills in your existing role. Depending on your company’s culture and management structure, you may be able to pitch an idea for a new job description or a new project.

Engage with the community

Making a change doesn’t happen in a vacuum. In order to move into a new role or industry, you need to connect with other people in that community. Find a local in-person meetup and identify a few people you want to speak to. Sometimes, it’s easier to connect at an event with a topic rather than an open networking event because it offers a built-in conversation starter. Attend a hackathon or volunteering event to meet other folks and apply your skills to solve a real-world problem. Join an online community or Twitter chat to answer questions, offer help, and connect with others. Networking with others is often framed as a transactional affair, but remember: you have skills and perspectives that another person may not have. In each interaction, you have the potential to help another person just as much as they can help you. Reflect on each of these conversations as you learn more about the industry and role. Does your image of the role stand up to new information? Or is it not what you thought it would be?

Find support to hold you hold yourself accountable and stay on track 

The exploration phase of a job search can be both exciting and scary. Being vulnerable and open to new people and experiences can trigger fear and anxiety. 

During this phase, it’s important to surround yourself with a support system to hold you accountable, validate your progress, and keep you on track. Some people have mentors they can turn to for advice and new perspectives. Other folks hire a coach for this same purpose. Maybe you have friends going through the same phase. Or perhaps there’s a local group that offers support during this time. 

Finally, give yourself the space and grace to take your time. When we’re in an unpleasant situation, it’s easy to jump at the first thing that is “not that” for the sake of making any change at all. Do your best to resist that urge and instead, tune in to your gut. Ultimately, no mentor, colleague, coach, or friend knows what’s best for you. Only you get to decide, and those answers take time to uncover. 

To quote Olympic runner Dan Browne, “For me, races are the celebration of my training.” Consider this guidebook your training. You’ve done the work, now go run your race. Take a moment to assemble your race plan for the week.

What small steps can you take to explore new possibilities this week? 

This post is an excerpt from Meg’s forthcoming book, Find Your Way Forward: A Step-By-Step Guide to Uncovering Career Insights and Charting Your Own Next Move. The book launches April 14th, 2020 on Amazon.