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. My clients progress quickly and powerfully, making strides with income, balance, stress, marketing, client onboarding, mindset, confidence and so much more.

Before we start working together, I recommend that we get to know one another by doing a free business audit session. You’ll get a chance to figure out if my coaching style is right for you. (If not, I’m happy to give you a referral!) And we’ll also make a game plan for tackling your challenges head on.

Popular coaching packages:

Join a cohort of self-employed creatives who want to move from reactive to proactive. The goal of the program is to help you feel more in charge of your work as you level-up your financial systems, add in client stability stability and nail your branding. Each month, we’ll address a new topic. All members get access to a growing library of resources, including templates, spreadsheets and beyond.

Investment: $149/ month

Building a creative business? Thinking about leaving your full-time job to go out on your own? Need to reset your current business structure? BUILD is for you. 

The BUILD program is focused on launching (or relaunching) you into the world of business ownership with confidence. During your sessions, you’ll learn about finances, marketing, building a business that supports your life, mindset tools, and beyond.

3-month plan investment: $999/ month

4-pack investment: $1260

UNLOCK is a 90-minute 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 feelings and how to strategically move forward. You'll walk away with an action plan, dozens of new ideas about how to approach your work, a better understanding of yourself and a roadmap for implementation.

Investment: $630

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!

  • Yes! I occasionally work for publications like the New York Times and the Wall Street Journal, and I create content for brands in the psychology, self employment, personal development and parenting spaces.

  • 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 Mindset Mastery 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