Coaching with Jenni is a transformative, action-oriented process based on curiosity, accountability and authentic conversation.

Unlike most of the people in your life, a coach isn’t in the box with you.

As your coach, it’s my job to challenge you, help you grow, and stand with you as you push through the barriers between where you are now and where you want to be. It’s not easy work but it is supportive, fulfilling and growth-oriented.

I take a unique approach to coaching that you may not have experienced before.

I pair traditional life coaching tools (like asking deep questions and spending time on your mindset) with strategic business consulting, plus intuition-led insights. This combination of witchy magic, practical application and reflective processing helps my clients progress quickly and powerfully, making strides with income, stress, marketing, branding, systems, mindset, confidence, and so much more. In short: They start to show up as their most powerful selves right now because we’re doing the kind of inside-out work that sticks.

“Oh gosh, where do I even begin? Jenni is a breath of fresh air when it comes to coaching! She is as genuine and compassionate as they come. She's helped me overcome mental blocks and successfully map a way out of my last full-time job back into full-time entrepreneurship. I wasn't sure it was possible (especially as a new mom), but Jenni leads with so much heart and empathy. And more than anything she shows me what's possible (and helps me get unstuck when I need it). As a result, I had back-to-back $10k months and my business continues to thrive. I know this is in large part thanks to Jenni's coaching and kindness!”

-L’Oreal Thompson Payton; Brand storyteller, Bookstore owner, Author & Speaker

Learn more about Jenni’s coaching programs:

Note: Jenni’s books for 1-1 coaching are currently full, and will be through January 2026. To be added to her waitlist for 1-1 coaching (which can include membership in the next round of The Council; a 4-month deep dive in the PLAY program; or an UNLOCK strategy sprint), fill out the intake form at the button below. Jenni’s team will get back to you with more information shortly. That said, several of Jenni’s group programs, including those below, are currently enrolling!

I can't express how much growth I've experienced in my time doing 1:1 coaching with Jenni. Her generosity with her time, experience, and resources is unparalleled.

She helped me understand what was getting me stuck in numerous places, and then provided the tools and questions to help me get unstuck. I feel clearer and 100x more confident in the future of my business thanks to my work with Jenni. And maybe most importantly as a solopreneur, I feel *patient* and I believe in myself. I'm so confident Jenni will be a guiding force in my business for a long, long time, and I'm so grateful to have her.

-Sydney Connolly, Life Coach for High Achievers

In my coaching rooms, we will always honor the following value system:

Reciprocity

In this space, we give as much as we get. We practice open receiving, and create a clean relationship with clear boundaries, excellent communication and best intentions. In my business, I make every effort towards accessibility by mixing low-cost offers with higher-cost programs, offering sliding scale options and scholarships, and donating time and money to my local community.

Non-judgment

Judgment causes shame and a lack of safety for most people; curiosity is the energy we bring to this coaching space instead. What I’m saying is that you can be your full self here, showing up however you feel on any given day. Cue the magical possibilities that come to light when unconditionality governs the energy.

Truth

It is my direct promise that in my coaching rooms, you will always receive the truth, and I ask that you speak the truth about your own situation as well. For many people, truth & transparency can feel edgy. But this coaching relationship gives us an opportunity to practice being honest, releasing people pleasing and asking for what we really (truly) need.

Flexibility

Boundaries are key, but so is flexibility. Everyone I coach has a complex, full life. With that in mind, we hold each other to the standard of truth while also making space for conditions to change, deadlines to move and assumptions to be explored. When we release the grip of control, creativity can help us find unique solutions.

Kindness

At the root of every program I design and every relationship I begin, is kindness. We make every effort to assume best intentions, practice empathy and compassion, and take intentional time to make decisions — on behalf of ourselves and others. In every program I offer, kindness is a core value. Members will be removed if unkindness, bullying or any other similar behavior occurs.

Human-first action

I am anti-capitalist, anti-corporation, anti-bully. I create spaces where your human needs come first. I stand for equity, affordable and gender-affirming care, values-before-money approaches to business and collective community spaces that prioritize being supportive of the natural world and one another.

Frequently Asked Questions

  • In a word: Intuitive. I’m well-known for sensing the thing you’re afraid to say out loud, and bringing it into the open.

    I often explain that when I’m coaching you, I see the future version of you immediately. And when I show up to coach her, we get to collapse time and powerfully move you into the future right now.

    I also believe that you’re the expert in your life and I’m the expert of the coaching process, so I take a collaborative approach to this work. We’re building something together. While the self-employment industry might encourage you to trust external rules and strategies, I believe that you already know so much about what’s best for you. I help you build a business based on those authentic, truth-filled insights, which I believe is a powerful recipe for sustainable growth.

    I make every effort to be completely present in our sessions and to hold space for you to work through whatever you need to work through. But you’ll also find that I’m not afraid to ask tough questions and push you a bit when I think there’s something we’re not addressing.

    If you follow me on social media, you’ll also know that I’m bold and adventurous — but I’m a mom, too. I bring a playful, brave energy to our sessions, combined with a nurturing approach, to help you feel excited about what’s next.

    Finally: I’m highly organized and love making order out of chaos. And I also bring my many life experiences to our sessions together, including becoming a parent during a pandemic; being laid off; dealing with PTSD, panic attacks and generalized anxiety disorder; leaving my fundamentalist Christian upbringing behind and reclaiming my own spirituality; and so much more.

  • Great question! Both use similar processes but they endeavor to address different things.

    Therapy is right for you if you’re dealing with old patterns and memories that keep you from moving forward. Mental health struggles (like anxiety, depression and chronic burnout), addictions, and traumas are best addressed by a trained therapist.

    Coaching uses psychological practices similar to therapy but in service of moving you from functional to optimal. During a coaching session, we focus on the present moment and we’re always working toward an outcome. You’ll walk away from the session with a clear idea of what to do next. We will occasionally deal with situations and relationships from your past, but in service of helping you move forward. Growth is the goal!

  • Consulting involves getting advice or feedback from an expert in your field. While I will occasionally offer advice, my primary coaching approach does not involve teaching you how to replicate exactly what I’ve done in my business.

    I believe that we’re all different and there’s a unique path that’s just right for you. What worked for me isn’t likely to work for you in the same exact way.

    In other words: You’re the blueprint in this room! No one like you has been here before, so we’re going to build an all-you approach to your work.

    (That said, I’m always willing to share my experiences if you ask!)

  • Are you building something? Are you at an inflection point in your career? Are you feeling bored, burned out or frustrated by your current business and/ or life approach? You’re in the right place.

    If you’re starting a creative business, planning to leave your job for something new, feeling stuck in a rut with your work, or looking to create a better structure for a business that already exists, coaching will be helpful for you! It’s all about getting clarity and accountability as you chase down big goals.

    Coaching is also a useful space for making big decisions or growing new skills like negotiation, confidence, and boundary setting. And I specialize in soul searching, existential doubt and figuring out your purpose. Hit me with the big stuff!

  • I have a bachelors degree from Bucknell University in psychology, and a masters degree in communications (with a focus on magazine and science journalism) from Boston University.

    I was a full-time editor at MedTech Boston, Upworthy and Wirecutter (New York Times) before being laid off, then launching my own freelance writing business.

    Since then, I’ve run four businesses: A coaching company; a community-driven organization based on a popular podcast; an agency; and a freelance writing business.

    In 2018, I completed a 200-hour training in meditation and yoga with Sendatsu Evolution, and in January 2022, I completed a one-year professional coach training with IPEC, which is an International Coaching Federation (ICF)-accredited program. I’m a CPC (certified professional coach) and an ICF member.

    I’ve also completed financial trainings with Kate Northrup; scoped out brand copy writing trainings with Simone Grace Seol; done deep marketing, branding and soul work with Amber Lilyestrom; and attended workshops and intensives on communing with the soul of your work with Nisha Moodley. I’ve also undergone two guided plant medicine journeys.

    I read deeply about somatic work, trauma, neurodivergence, caregiving, attention, accountability, motivation, psychology, and beyond.

    I’m constantly investing in my own personal growth, re-patterning and understanding of how people are best able to unlock their own personal power.

  • Practically, you’re paying for our time together, whether that’s 1-1, in a group setting, or in my mastermind program. The payment includes prep for our sessions, follow ups, Voxer or email support between calls, document review, and so much more.

    I have a very specific pricing approach that I’m happy to teach you!

    But I also want you to remember: Coaching will help you find a sense of clarity that often, but not always, leads to higher pay and lower stress. Yes, you’re paying $1,000, but you’re likely to get $10,000 back (or more). My clients find, time and time again, that every penny spent is worthwhile. Plus, you can write it off as a business expense!

“Working with Jenni has been a game-changer for my business, which has blossomed with Jenni’s help with both structure and finance as well as her ability to intuitively listen and discern what truly lights me up and what I have resistance to.

As an entrepreneur, I sometimes struggle with the “should” obligations from the outside world versus my heart desires. Jenni pushed me to look at what I truly want right in the eye— and go for it. She leads by example in doing this work herself - and she also gives tools that fit my ways of working (that sometimes feel untraditional). This kind of validation and specialized toolbox particular for my business makes me feel like I have wings!”

- Lucinda Caldwell, community organizer, artist, founder of Giddy by Nature