Coaching Services

My specialty is working with creative professionals, artists and business executives coming from the music, entertainment, media, tech, finance and small business industries to move forward to their next level of success in:





Ask Yourself These Questions:

  • Are you a seasoned and successful executive in a career that is no longer fulfilling?
  • Are you an ambitious, self-disciplined individual driven by a strong personal desire to accomplish meaningful, important goals?
  • Do you find yourself facing a career change either by personal choice or circumstance?
  • Are you a busy professional seeking work-life balance?
  • Are you a student or young professional trying to determine your career direction?
  • Are your once healthy lifestyle habits resting too comfortably in a plateau?
  • Despite being motivated for a change, do you find it hard to be consistent and need to be held accountable?

If you answered yes to any of the above questions, than Smile Across The Finish Coaching is for you.


“After two Ivy League degrees and 18 years of following a relatively straight and prescribed career path in finance, I found myself feeling lost – unaccomplished, unfulfilled and unqualified to be doing anything other than exactly what I was doing.  At 40 years old, I felt stuck in my position – unable to start over and unable to leverage my skills to maintain or improve my compensation.  I started working with Tara six months ago in the hopes that she could help me identify career adjustments that would make me excited to get out of bed and go to work.

My experience with Tara was very unexpected, and magical in my opinion.  I had expected that we would have a few conversations about my experience and interests, and she would make some recommendations of career choices, help me with my resume and coach me for interviews.  Our engagement was nothing of the sort.  She literally deconstructed me….or rather forced me to deconstruct myself through a variety of exercises that I initially thought were a formality, but forced me to dig deep and ask myself some very hard questions.  I learned quite a bit about myself.  With this new and better information, together, we were able to identify a few interesting career choices that not only leveraged my existing skills (which I had very much discounted), but were also interesting and exciting to me.  This realization gave me confidence that I have not had for a long time.

Together we have worked through an execution plan to transition from my current career to my next.  She is with me and coaching me through every step of the way from my strategy, to my Influence Letters (aka Thank you notes), to evaluating my choices, to researching, and most importantly, to my emotions.  

I was an unassembled 1,000 piece jigsaw puzzle when I started working with Tara.  During each one hour session we are extremely productive in putting critical pieces together to see what my career path should, could, and will look like.

While I am sure Tara is quite adept at helping those who are interested to accelerate their careers on an existing path, she is VERY powerful in helping someone pivot their career after traveling down a long road and realizing they are lost.  

Lastly, I think it is important to point out that Tara is not a seasoned expert in my particular field (the old one or the new one), but accurately interpreted all of the complexity and minutia, and was able to weed through it to get to the core concepts and issues that needed to be addressed.  Regardless of your industry, I am very confident she will be able to guide you and provide powerful insight.” – Amy, Marketing Director to Hedge Fund Group / Entrepreneur  

“Tara was invaluable in helping me find myself in my career journey. She knew when to ask a question and when to suggest an answer. She knew when I needed someone to build up my confidence and when I needed someone to question my assumptions. Her coaching has been integral to me not only finding my next career move, but grow as a person.” – Zach Hochkeppel, Senior Marketing Executive/  Former GM & SVP Blue Note Records

“Tara’s executive coaching has been indispensable to my leadership development due to the core skills she helped me hone in and develop. Tara’s ability to truly listen and hear my challenges and compartmentalize the steps needed to set a structure for growth has been indispensable. Moving forward, these skills will be pivotal as I work to advance further in my career.” – Jill W., Equity Capital Markets Product Head and Chief Operating Officer at Credit Suisse

“There are moments when you’ve been working for so long that you need a refresh.  I never thought I needed a Career & Executive Leadership Coach, especially after working in an industry for so long. I thought I knew it all. Times are changing and adjusting to those changes is how you stay relevant. Tara’s personality puts you instantly at ease to think clearly and I was able to speak freely, understand next strategic steps and exceed at executing a plan for my career and leadership development.” – T.P.M., Music Industry Executive from a major music label

“As an aspiring music artist/ songwriter/ producer caught in the crossroads of uncertainty and insecurity, Tara helped me clarify my goals and career path by making me ask myself tough and relevant questions. She’s an Olympian-level listener and a positive presence. I’m surprised to come to know myself better after going through her coaching services.” -J.E., Artist/ Songwriter / Producer

“Tara coached my business partners and I on launching our new business in Florence, Italy- a school of Italian language for foreigners called ‘Italian Me’.  From the very first meeting, she was extremely helpful at guiding us to clarify our many ideas and dreams into achievable goals and supported us throughout every step of launching and growing our new business.  We had a vision stuck in our minds and working with Tara as our coach & marketing consultant she helped to bring the concept out of our heads, to build it, step by step.  She is always positive and finds the perfect words to encourage us even when we thought that everything was too difficult and in a dark place. And beyond the words, she also has a unique knowledge of business development & creative marketing strategies which has been an added value to her coaching services. I strongly recommend Smile Across The Finish Coaching if you want to be successful in life and business.” – Francesca Bertocci, GM & Director,

“I am amazed by how much the group career coaching sessions with Tara Chiari are helping me to achieve my objectives. The group sessions I am attending include a variety of professions and personalities  – yet Tara’s intelligent, insightful, and flexible approach achieves an atmosphere of sharing and learning. She adapts her considerable skills to each individual to such an extent, that I am beginning to see the blind spots disappear that were hampering my advancement, and as a result, the responses I am getting in my search for work are great!” – Ilil Arbel, Freelance Writer / Published Author

“I reached out to Tara as I knew of her entertainment industry and coaching experience. I’m a singer-songwriter who also has had a corporate job. Tara not only helped me find a job that was aligned with my true goals and value system, she also supported me in my growth as a musician. I also appreciated her flexibility for scheduling calls and availability via email in between sessions.” – S.Z., Musician / Senior Project Manager (PMP) in Healthcare, Automotive & Business Consulting

“I’ve always been a fan of Tara Chiari in every way and I’ve loved seeing her evolve from a music biz executive role towards an even truer passion- helping other professionals in the entertainment and many other industries achieve their personal best. As someone who retained her professional services, she artfully helped me reframe a daunting and nuanced negotiation into a strategic way for me to get closer to my bigger picture goals. Tara is someone of the finest character, wisdom and experience- a bona fide triple threat. Anyone needing professional coaching should turn to Smile Across The Finish Coaching.” – J.L., Senior Brand Marketing & Communications Executive

“What has worked best for me in working with Tara as a Career Coach is that she combined her expertise as a Life Coach and Executive Coach to guide me through my career transition from all different angles that I didn’t realize were important or related. Tara was also very generous with her time between sessions with check-ins and feedback on communication materials which I found incredibly helpful to my job search success.” – Marc R., Financial Accountant

“A bright and positive coach who pushes for the best in her clients!” – MZ, Public Relations & Media Professional/ Recent College Graduate


Career, Leadership & Personal Development Coaching