How Do You Rebuild Your Confidence After Taking a Career Break? | A Real Coaching Conversation with Amanda Wood

Summary:

Returning to work after time away can bring hope, excitement, and more self-doubt than many people expect.

This week on The UpLevel Podcast, our host Christie Mann coaches multidisciplinary creator Amanda Wood through the very real experience of preparing to return to the workforce after an intentional 18-month career break.

Amanda has spent her career leading creative teams, building brands, and running her own agency. During her time away, she developed greater clarity about the kind of work she wants to do, the life she wants to create, and the values she refuses to leave behind.

Together, Christie and Amanda explore how coaching can help shift attention away from the inner critic and back toward possibility. Through future visioning, embodiment, metaphor, and practical coaching techniques, Amanda reconnects with what gives her energy: meaningful collaboration, creativity, trust, flexibility, and contributing to something larger than herself.

One of the most powerful moments in the conversation comes when Amanda recognizes that the loudest voice in her head is not the most truthful one. As Christie reminds her, self-doubt often grows louder when we're getting closer to something that truly matters.

Whether you're returning after raising children, recovering from burnout, taking a sabbatical, caring for loved ones, or intentionally stepping away to reset, this conversation offers encouragement and practical coaching tools to help you move forward with greater confidence.

In this episode, we'll explore:

• How to rebuild confidence after taking a career break

• Why self-doubt often increases before meaningful change

• A coaching exercise that creates momentum through future visioning

• How to reconnect with your strengths instead of your fears

• Why values should guide your next career move

• Practical ways to move forward before you feel completely ready

Order of Topics:

• Designing the Coaching Alliance

• Naming the Coaching Topic

• Creating a Future Vision

• Identifying Core Values

• Discovering What Creates Energy

• Learning From the Career Break

• Recognizing the Inner Critic

• Reframing Self-Doubt

• Building Momentum

• Celebrating Personal Strengths

  
  

Action Items:

• Create a compelling vision of your future.

  • Spend time imagining what success looks and feels like. The clearer your vision, the easier it becomes to move toward it.

• Finish the work before you judge it.

  • Don't let perfectionism stop you from completing your portfolio, résumé, website, or application. Progress creates momentum.

• Recognize when your inner critic is talking.

  • Notice the voice that tells you you're not ready or not good enough. It doesn't have to make your decisions.

• Take one meaningful action before you feel fully confident.

  • Confidence grows through action. Start with the next step that's in front of you.

• Choose work that energizes you.

  • Pay attention to the environments, people, and projects that leave you feeling inspired instead of depleted.

• Protect the routines that support your wellbeing.

  • As you return to work, continue making time for movement, reflection, rest, and the relationships that matter most.

• Let your values guide your career decisions.

  • Look for opportunities that align with what matters to you, including collaboration, flexibility, trust, creativity, and family.

• Build accountability into your goals.

  • Share your deadline with someone you trust. Accountability can help you follow through when motivation fades.

• Remember what you've learned during your career break.

  • Time away often brings clarity. Don't leave those lessons behind when you return to work.

• Stay connected to the version of yourself you're becoming.

  • Return to your vision often through journaling, visualization, or reflection. Let that future pull you forward instead of allowing fear to hold you back.

About Amanda:

Amanda Wood is a multidisciplinary creator with a degree in fine arts and over 15 years of experience as a creative professional in advertising and communications. She has worked in large agencies as an art/creative director for clients like Toyota, Air Canada, McDonald’s, and Mazda and later founded her own agency specializing in bringing new brands to market. She is also a certified yoga instructor and a student of acting and is engaged in many community-based creative projects such as sign painting, schoolyard revitalization, and children’s face painting, to name a few. Amanda lives in downtown Toronto with her husband, six-year-old son, and dog, Cosmo.

🎉 The UpLevel Podcast was listed as one of the Top 10 Best Coaching Culture Podcasts!!! https://podcasts.feedspot.com/coaching_culture_podcasts

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About UpLevel Productions: Founded by Christie Mann, MA, CPCC, PCC, and Rachel Baldi, CPCC, PCC, UpLevel creates, produces, and delivers Transformative Experiences, Workshops, Training, Events + Media that develop leaders who make our world a healthier, more alive, and connected place to be. As Associate CTI Faculty Partners, UpLevel is licensed to sell, produce, and deliver Co-Active coach training and leadership development programs around the world to support the transformational growth of individuals and culture inside the workplace and organization. www.uplevelproductions.com Instagram @uplevelproductions Facebook & LinkedIn @uplevelproductionscompany