The road not taken: how to make big career choices with intentionality

The road not taken 

Many of my clients come to me at a crossroads: should they continue down a familiar career path, like staying with a company they’ve worked with for years, for example – or choose a new, less familiar path, perhaps starting their own venture or stepping into a new role with new responsibilities?

More often than not, clients invoke Robert Frost’s classic (nay, iconic!) poem The Road Not Taken during these sessions, since its title alone is used as shorthand justification to step boldly into the unknown. 

But if you read past the title, the poem actually suggests a more nuanced truth: both roads are equally untrodden. The significance of the selection doesn’t lie in the quality of the chosen option itself, but in the way we approach choice, and the meaning we later ascribe to our decision.

While this takeaway may be slightly less romantic than that of popular interpretation, it offers a reassuring message to those contemplating a bold career move. There is no singular “correct” career path; leading with purpose and intention makes all the difference.

So, how do we cultivate that intentionality when choosing a path? Let’s get into it.

Should I stay or should I go?

Take my client, Regan. A few months ago, she came to me with a heavy question. Should she leave her full-time job to start her own business? 

There were a lot of factors to consider: 

• She had recently become a new mom, and she wasn’t sure how this huge shift in her personal life impacted her professional aspirations

• She had 6 years of progressive success at a PR agency under her belt; she loved her work and the close relationships she had with colleagues and clients

• She had always dreamed of branching out on her own, but wasn’t sure exactly what she wanted from that experience and what she would get from it 

Staying at her job would mean: 

• Stability: a regular paycheck, predictable hours, and long term security 

• Familiarity: known challenges, known rewards 

• Community: continued partnership with beloved colleagues and clients 

• Linear career growth: an opportunity to continue climbing an established ladder 

On the other hand, founding her own venture would offer:

• Change: a blank slate, new projects, new responsibilities, and new challenges

• Agency: a chance to selectively pursue the work that she found most meaningful and personally aligned with her interest and goals  

• Flexibility: the ability to shape her day around her new lifestyle as a parent

• Skillbuilding: an opportunity to flex and strengthen new skills

But how could she choose between the familiar and the unknown? Her decision carried real consequences for her livelihood, goals, and sense of identity, and when she tried to work through it, she’d hit a dead end. 

“Working through this big question on my own wasn’t working,” Regan says. “I felt a lot of excitement about what the future might look like, but I also felt overwhelmed by the different paths laid out in front of me. I knew that without stepping back and proactively taking stock of what I wanted, I wouldn’t feel as confident that I had made a thoughtful decision. I needed dedicated time and a clear framework to guide my next step.”

We set out to organize the many thoughts swirling through her head so that she could better understand what she truly needed moving forward. 

Where do I even begin?

To start, Regan and I focused on building a structured, personalized criteria that we could use to compare these two seemingly opposite paths “apples to apples.” The first goal was to understand her wants and needs for this specific chapter of her life and career. With that in mind, we sat down together to understand:

• What do you want to give at work? What skills do you want to apply in your day to day? What previous experiences do you want to leverage in order to succeed at the tasks and projects on your plate? 

• What do you want to receive at work? What do you want to feel in your work environment? What kind of collaboration, growth, and ownership is important to you right now? 

• What are your non-negotiables? If we prioritize all of your criteria, what comes out on top? 

• What are you willing to sacrifice? Each option requires concessions; which ones are you most willing to make? 

• What were the potential risks, and how might you mitigate them? What are your biggest fears about moving forward? What safeguards can we create to prepare for those possible outcomes ahead of time?  

  
  

The product of this reflection was a tool that we could use to evaluate each path against a criteria that was by, for, and of Regan in this moment of her life. 

Quantitative data meets qualitative feelings

Once we had a working draft of Regan’s criteria, we put it to work. We used it to evaluate each idea, and scored each opportunity according to her wants and needs, resulting in a heatmap that helped us visualize the pros and cons of each pathway she was considering. 

An excerpt of Regan’s criteria and scoring system. 

But we didn’t stop there; we made sure to see what we could learn from each score by asking: 

• How do you feel about the resulting scores? 

• What trends do you notice? 

• What is true for the paths you’re most excited about?

• What is true for the paths that you’re least excited about?

  
  

This process wasn’t about steering her toward one outcome or another — it was about empowering her to consider each option fully, both intellectually and emotionally. And it yielded a clear winning next step for Regan.  

Acting on an informed, intentional decision

After articulating her wants and needs, ranking them by importance, and evaluating each path against them, the last step was to act in alignment with her priorities. 

By giving both paths their day in court, Regan was able to make a calculated and informed decision, and (drumroll, please!!!) the business that she founded in 2024, Relay Climate Communications, is already thriving. Go Regan! 

“The evaluation process was so useful to me because it held me accountable to my priorities,” reflected Regan. “Our work helped me develop a list of guiding principles that I could use to inform my next step, and even though it was at times compelling to default to the familiar, it became clear what it would look like to act in alignment with what I truly wanted.”

At the end of our time together, Regan knew that she had made an informed decision, and that confidence continues to pay returns. When striking out on her own gets tricky (every option comes with its challenges!), she knows that she left no stone unturned during the decision making process, giving her confidence that she made the “right” choice. 

“The framework is an evergreen tool that I’ve revisited since my career pivot,” says Regan.  “While my choice still meets the guidelines and priorities in my framework today, I appreciate that someday those priorities will shift. I love that when I’m ready for my next career chapter, I’ll be able to use it as a starting point.”

Evaluating the roads diverged 

In Frost’s poem, the narrator’s choice lacked real stakes — both paths were equally worn, and the meaning came from how the decision was later framed. But in our careers, the stakes couldn’t be higher. Every course of action has consequences for one’s personal fulfillment, financial health, and sense of identity. That’s why centering intentionality at every inflection point is so important. 

If you’re standing at your own crossroads and want support as you chart your path forward, let’s talk. I’m here for you. :)