Live Confidently & Unapologetically.

Support for women who are childfree or just figuring it out.

Get Unstuck. 

Coaching helps you identify what you truly want and sets you down that path.

If you want to change your life, you need a safe space to explore ideas and possibilities. You need someone rooting for you, holding you accountable, and guiding your exploration. Coaching provides all of that.

You’d be surprised how quickly transformations can happen. Women struggling with the decision to be childree are usually past that within a few months.

Once fear and doubt are gone, you can pursue your biggest dreams with confidence. 

A few months from now, you could be actively creating your dream life. Ready to explore what that might look like? 

Schedule a clarity call. It’s FREE!

If you want to learn more about me, your coach, check out the about page.

3 Steps to a More Fulfilling Life


We clarify your goals by exploring all the unique things that make you who you are.


 Imagine all the possibilities available to you. Envision yourself living your best life. Map out the steps to get there.


Set milestones, and take action. I’ll keep the momentum going by checking in and holding you accountable.

How Coaching Works

Coaching focuses on building clarity, identifying a desired outcome, and working towards it. You’ll meet with me regularly to discuss your life and where you want it to go.

The goal is to create the future you want, starting right where you are.

What Coaching Is


Coaching focuses on the present and the future. It’s goal-oriented and centers around creating the best possible life for you.

Equal Partnership:

You have an equal partnership with your coach. Your coach won’t tell you want to do or provide answers to life’s biggest questions. Instead, your coach helps you discover those answers yourself and helps identify roadblocks.


You are the expert of your own life. Coaching helps you tap into your inner wisdom. Identifying what you truly want involves self-exploration, self-knowledge, and self-direction. That’s how you get where you’re trying to go.


Talking will help you get clear on what you want, but only action will get you there. You’ll set milestones for achieving your goals, and your coach will hold you accountable.


What Coaching Isn’t

Coaching is NOT therapy. 

Therapy helps make sense of the past. The goal of therapy is often to heal trauma, resolve emotional issues, and overcome recurring pain. Coaching can be used in conjunction with therapy, but it’s not a replacement for therapy.

What You Get When You Hire Me As Your Coach

3 months of weekly one-on-one coaching

50 minute sessions take place via phone or Zoom

Action steps & exercises to move you towards your goals each week

Unlimited access to me via email for questions and support

Comprehensive follow-up emails after each session

Free access to the WNK-Club

Your first call is free!

Success Stories

“I’m more confident and self-compassionate now Anna did a great job of holding up a mirror for me and helping me see my strengths. She helped me conceptualize my dreams in ways that made them feel like real possibilities. She gently invited me to challenge my fears and self-doubts in ways that always felt caring and like she was on my team. I now feel more confident and self-compassionate after working with Anna, and I see a path forward more clearly now. I highly recommend working with Anna and investing in yourself through her coaching."

– robin

“Powerful breakthroughs, without feeling pressured I got in touch with Anna when I was busy developing my new business. I felt I needed some help, in particular with building self confidence, so that I would keep pushing myself and getting to where I want to be! I loved her personality, very gentle and calm, understanding, and compassionate. Most of the coaches I had before felt pushy, but she managed to help me have some powerful breakthroughs during our sessions, without feeling pressured.

– Madeleine

“The coaching process with Anna still blows me away! I reached out to Anna in the midst of the Coronavirus pandemic. Our family had been working through major changes just like everyone else in the country. We were adjusting work schedules, school schedules, and daycare schedules. During this shift of more concentrated time at home, I felt a deep desire to reflect more intentionally on how more 'family centered' life could look during this period and be sustained after everything moved into a new normal. I brought these muddled but heart driven ideas to Anna and she didn't even flinch. She was excited for the challenge of sorting through the questions, identifying workable and flexible goals, providing affirmation and active listening, and guiding me forward with encouragement through this reflective journey of 'what if....'

– Sarah

“The most significant metamorphosis of my life. Let me start by saying that I've used a variety of teachers, coaches, and mentors in the past, so Anna Olson Coaching wasn't the first coaching experience I've had. However, her kindness, grace, and understanding is a rare commodity. She helps you pull back layers using questions and sort through the mixed messages in your mind and soul. I met with her for six weeks, and throughout that time, I had one of the most significant metamorphosis I think I've ever had in my life—both in coming to terms with some faith things and business growth situations. Anna is a serious Godsend. If you find yourself stuck, confused, or knowing that there is something there that keeps getting in your way but can't put your finger on it, I'm telling you, book with Anna now. Save yourself time and energy by going to someone who invests in who you are.