It’s amazing to think that I’ve been running my company, WOKEN, for 7 years now. After 7 years of guiding diverse clients through the twists and turns of career development, I’ve come to see some recurring dynamics and effective strategies that help people make real progress. Each client is unique, but there are patterns that reveal what helps people succeed, what holds them back, and how they can leverage their strengths for career growth. Here are the main insights I’ve gained about coaching people through these complex journeys.

1. Mindsets Will Affect You, Whether you Believe it Or Not

If you’re feeling blocked from working on your resume or networking or any career activity, there is something underlying that. Each person has their own limiting beliefs -- it’s key to figure out what’s going on underneath the surface as it WILL affect your choices and your actions, one way or another, so know that your drivers and intentions are coming from the right place and if you need to, spend time to work through, understand, and alleviate any limiting mindsets. One of the most common blockers is not a lack of skill but the fear of failing or making the “wrong” choice. There are often assumptions about what you can or can’t do, what you should or shouldn’t do. These fears can be paralyzing, causing clients to avoid action or to overthink decisions. Helping clients see each career step as an experiment rather than a make-or-break decision—can be incredibly freeing. Rather than feeling like every choice is an end-all-be-all, you should be sufficient thought into your next career step, and then actually take that step, allowing yourself to learn from it versus never experiencing it, and never learning whether it worked or not. Don’t debate your choices forever -- be thoughtful enough to take some good steps forward even if they may not be perfect. Take calculated risks, learn from your experiences, and you’ll move forward faster​​.

2. Accountability = Experimentation + Self Awareness

Being accountable to your goals means that you put in sufficient time towards them, it means that you structure your day properly, you’re prioritizing and balancing what activities to do, when, and for how much time. You’re not just “doing the work,” but you’re thinking about how you’re doing the work. Finding an accountability routine that works takes self awareness + experimentation. 

3. Self-Awareness is Key, but It Needs to Be Practiced

Clients who understand their strengths, weaknesses, values, and motivations generally make quicker and more confident decisions. But self-awareness isn't something that happens overnight—it requires intentional reflection and practice. For example, journaling about or talking through one’s career experiences or documenting insights from networking conversations allows clients to see patterns in what they enjoy and what drains them. Those who are willing to put in reflective work on an ongoing basis often find clarity sooner and are more aligned with their career choices​​.

4. Career Clarity Frees Everyone

For the many clients that I have helped to figure out their ideal career path, it makes their entire career trajectory feel easier, more exciting, more relaxed, more rewarding, more successful, and more fun. So many people come to me unsure if they’re in the right role, industry, or work environment -- and many are not. But when we get specific to identify where they align or don’t align with past experiences, and what they truly want moving forward, that true sense of career clarity and certainty is a game changer. It makes their job search flawless, their interviews compelling, their job fulfillment skyrocket, and their overall career growth feel organic.  

5. Documentation is Underrated

The simple act of writing down your thoughts or next steps, and sharing these with your coach, can do wonders for your progress. If you’re coaching with someone, don’t just have conversations -- go beyond it. When things are left solely to conversation, it can feel hard to grasp, to know where you started and where you finished. I find that by physically mapping out someone’s plan on paper, it can make the roadmap feel more clear and manageable. Plus, when challenging experiences arise or even a-ha moments and reflections, using documentation as a way to process is critical to progress. 

6. See the Hike as One Step at a Time, Don’t Look at the Mountain

Many clients feel the pressure to make big, transformational changes quickly, but in practice, the real breakthroughs often happen through small, consistent efforts. Whether it's setting time each week for skill-building or networking, incremental steps tend to build confidence, reveal new insights, and create sustainable change. You can make a HUGE career pivot by following this exact model -- if you commit to those small steps for several months. The challenge, however, lies in embracing this steady pace, and focusing on what’s directly in front of you, while having periodic check-ins with how you’re doing towards your broader goal, rather than expecting rapid shifts. Helping clients set realistic, weekly goals and celebrating those smaller wins can make all the difference in maintaining momentum​​.

7. Reframe Challenges Into Creativity

It is rare that we are taught how to truly be creative. To me, creativity  means when you hit a roadblock, you embrace new options of how to reach your goal. You see the positive potential in what you can do or try next, if it's different from your past routes of action. Clients who actively seek and incorporate feedback, whether from mentors, peers, hiring managers or even by being honest with oneself, often accelerate their growth. Being open to making pivots can feel uncomfortable and challenging to most, but clients do well when they reframe and feel more nimble. Most people don’t love change, and yet careers require each of us to be able to reflect often on what is working and what isn’t, as honestly as we can, to take a better next step forward. Successful clients learn to separate their self-worth from external opinions or even from failed experiences, knowing that anything that may feel like it’s “not working” is just information they can use to make themselves better. Clients do well when they adopt an action-oriented, constructive, forward-thinking mindset where any “negative” experience is actually an opportunity.

8. Leverage Your Wide Perspective

By meeting with so many people in discussing similar topics, I can easily see the variances and similarities between people and how they operate. No two clients are the same, so coaching needs to be adaptive. While frameworks and step-by-step guides are helpful, I always meet clients where they are. Some clients need more mindset coaching, while others benefit from tactical guidance. Some need tough love, while some need a listening ear. Some come with an agenda, others need you to guide. Some clients need to figure out what is “good enough for now” based on their goals, needs, and timeline, so they’re not stuck in analysis paralysis, whereas others are ready to shoot for their dream roles. Personalizing the approach and staying flexible by listening closely, asking probing questions, and adjusting plans whenever necessary, allows clients to feel seen and supported. Clients also often benefit from my wide perspective from having met with hundreds of professionals over the years. Because of this, I can easily give people guidance on where they stand -- this is not to compare them to others, but rather, to help them see the bigger picture, to take a step back, and to trust that we can effectively plan to ensure they meet their goal, in a way that can be truly beneficial.

9. Resilience is Built, Not Innate

Career paths are rarely straightforward, and setbacks are part of the journey. Clients who learn to build resilience or adopt a mindset where they are more comfortable with ambiguity and change tend to be able to feel happier overall and make steady progress to make their situation even better. Encouraging clients to approach career growth as an evolving process rather than a series of perfect steps fosters the resilience they need to keep going, even when the path is unclear​​. If you can feel “informed enough” with each step, like you did enough research, networking, and reflection to make a good decision right now, then you’re more prepared than most others. 

10. Learning + Reflecting = Clarity

Whether it’s a client learning from the people in their network, or myself as a founder learning from other founders or business coaches, learning is everything. When I’m not sure of a path forward, or when a client isn’t, learning is often the answer. When it’s not the answer, it’s a matter of self reflection. I have found that the combination of both learning and reflection is the key to clarity on your path forward.

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Coaching people through their career journeys is as much about developing mindsets and habits as it is about achieving specific milestones. Career success is built on small, intentional steps with a broader goal in mind + creativity/adaptability + self-awareness.