Coaching 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 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. This helps my clients progress quickly and powerfully, making strides with income, stress, marketing, branding, systems, mindset, confidence, and so much more.

Before we start working together, I recommend that we get to know one another with a free business audit session. Please book your 20-minute call below:

“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 freelancing. 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, Journalist, Author & Speaker

Popular 1-1 coaching packages:

Join Jenni for 3 months of a deep coaching relationship focused on taking a PLAYful, child-like approach to your business. We'll dig into what makes you unique, how to set up a workflow that works for you, and talk about what is blocking you from being fully expressed. You'll walk out with a game plan for ease, tools to use when you feel yourself stepping into hustle mode and increased self-trust.

Investment: $850/ month

Every quarter, Jenni offers one-hour small group coaching pods. The next round of pods will be focused on end-of-year reviews and will occur in December and January. Pods include a strategic coaching session with Jenni and three other solopreneurs who are hand-picked to support you. You'll also receive each other's contact info and may continue to meet after the fact (or text, or email) for accountability.

JOIN THE WAITLIST FOR THE NEXT ROUND

UNLOCK is a 75-minute business strategy session meant to help you figure out where you’re stuck in your business. Then we’ll lean into next steps, with a dual approach that addresses both your mindset and how to practically move forward. You'll walk away with an action plan, dozens of new ideas about how to approach your work, 2 weeks of email and copy support, and a roadmap for the future.

Investment: $699

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

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 also believe that you’re the expert in your life and I’m the expert in 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 that insight, which I believe is a true, powerful recipe for sustainable growth.

    I also 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 also a mom. I bring a playful, brave energy to our sessions, combined with nurturing, 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 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. That said, I’m always willing to share my experiences if you ask!

  • I run a content agency called The Riverwoods Media Group. Within that agency, I help teachers and emerging thought leaders create content in the form of newsletters, emails, podcasts and website copy. Learn more: https://www.riverwoodsmediagroup.com/

    I do not take pitches for products, as I no longer write product reviews or write for journalistic publications (apart from the occasional personal essay).

  • Are you building something? 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.

  • 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 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 and branding work with Amber Lilyestrom, and attended workshops on communing with the soul of your work with Nisha Moodley. I read deeply about somatic work, trauma, neurodivergence, caregiving, attention, accountability, motivation, psychology, and beyond.

  • 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.

    But here’s the truth: The number you see is commensurate with the value I provide AND the commitment you’re making. The more you pay, the higher the commitment, the higher the value, the better the results.

    And 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 $20,000 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!

  • I talk about self-employment publicly — and for free— all the time! Start by listening to the business podcast, The Writers’ Co-op, that I co-hosted for two years. You can also subscribe to my Third Door newsletter for free.

“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 a freelancer and 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