Coaching By Toby
Coaching By Toby
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I've Been in Your Shoes. Now I Help You Walk the Path.

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About Us

Life Coaching

CREDENTIALS

Associate Certified Coach (ACC) through the International Coaching Federation (ICF), the defacto standard for entrepreneur coaches and business coaches around the world


Certified Professional Coach (CPC) through iPec, a globally-recognized coach training school


Energy Leadership™ Index Master Practitioner (ELI-MP) to coach and debrief clients utilizing an assessment tool that measures the energy you bring to your day to day life and when under stress 


DISC to learn about your own personality and better understand why you may or may not be happy in your current situation, build stronger teams and discover the best ways to collaborate, improve workplace culture and cultivate effective communication and relationship-building strategies. Your DISC results are critical to the career coaching process.

Helping Those Who Crave Financial Freedom

Entrepreneur Coach, Freedom Fighter, and Unapologetic Dream Builder.

If you’ve ever thought, "I want to start a business but don’t know where to start," you’re in exactly the right place. I specialize in helping ambitious women break free from the grind and confidently navigate the real steps to starting a business for beginners — without the overwhelm, fear, or guesswork.


You’re not meant for the sidelines.


You’re meant to build something bold, beautiful, and entirely yours.


Whether you have no idea what kind of business to start yet or you're ready to escape the 9-5 for good, I’m here to show you how to move from dreaming to doing — fast, confidently, and with a lot more fun than you ever expected.


🚀 Let’s build the life and freedom you deserve — from scratch, and without the stress.

MY WHY

I ask many of my clients to define their "Why". If you can define your why, you can better determine what path is best for you. 


My Why is:

"Empowering others to achieve their dreams"

It happened by accident one day. After a random conversation with an incoming college student, they found their path. And then I started mentoring and found that I absolutely loved helping people find their way. So when I was searching for my next gig, coaching was literally screaming at me as the only path forward. And here I am!

MY PHILOSOPHY

I believe that we are all the experts in our own lives. And yet, sometimes we all may need a catalyst to reach your goals.  As an entrepreneur coach and career coach, I will be that independent voice helping you explore your potential and activate your vision.  

CHANGE AS A CONSTANT IN MY LIFE

My story is not linear. And change / transition was ever present.

I started my career in consulting at a company that became Accenture. I was a hyper-achiever who worked hard and played hard. In looking back, I was probably a bit restless and that is why consulting was so appealing to me.  I could be in different cities / countries solving different problems with different people. And I took advantage of it. I worked in five cities in three countries during my consulting career. I learned how to make friends wherever I was and make the best of my situation.


Transition #1 - Taking Risks

When I had a chance to leave this big consulting firm and go to a spin-off firm, I leapt at the chance. I took some comfort in that people I knew were also going to this new firm as well. And yet still, it was an adjustment.  It was a smaller firm and I was introduced to new levels of responsibility and expected to perform!


Transition #2 - Finding Something More Fulfilling

At some point I felt like my purpose was unclear and I wanted to leave. Consulting seemed a bit sordid and I wanted something more meaningful. I thought I wanted to get an MBA and go into the non-profit world.  I asked my mom what I liked to do when I was 5 years old and she said something that in looking back was so telling.


1) She couldn't keep me interested.  I was bored by her and clearly needed to go to school. A definite example of my low patience and restlessness. 

2) When she could get me interested, I liked to do puzzles. Problem solving. Clearly I was generally in the right job already.  


But I felt consulting wasn't in my long term interests, so I quit without a job (something I tell others never to do).  Then I got married and had dreams of buying a house and having kids.  Hello corporate job, good bye non-profit!


Transition #3 - Drudgery in Bureaucracy to My Comfort Space

The sliver of time I spent in "Big Corporate" was not my favorite.  Not enough shared goals. People were only out for themselves and progress was slow. While I was working full time and commuting two hours per day, I also built my own house. My restless took over again and I jumped to the software industry.  I found my place in product management. I loved solving problems and it scratched my itch for strategic thinking. I worked for two companies in the legal technology space and enjoyed my time there. Meanwhile, I adopted two kids and was trying to be a virtual superwoman. I switched to part time, but still worked a full time job.


Transition #4 - Entrepeneurship

After leaving legal technology, I started my own software company while I was going through a divorce, bought a house, and was 3 years from sending my oldest to college. I went almost 3 years without pay, trying to scrape by with some odd consulting gigs and AirBNB-ing my house. I have some great stories from that. It wasn't easy, but I learned a lot and the end result was more than positive.


Transition #5 - Back To The Grind

I sold the business with a positive exit and made two attempts at working at software companies as an employee, one of which took me into an entirely new space - FinTech. Having been my own boss made working at these companies difficult. I clearly needed to be in charge. So I left to ponder what I was going to do with the rest of my life. I didn't want to start another company at this stage. I didn't want to be an employee. But I was not ready to retire, nor dip into my retirement savings.


Transition #6 - Empty Nester

I left the suburbs of Chicago and the friends I had built over the years and moved downtown. My kids were out of the house (as it turns out temporarily) and I wanted to move to the bustling city. I learned to sail, signed up for a lease-share to sail Lake Michigan, went to plays, sampled some great bars and restaurants, caught up with friends that now lived closer to me, and had a great time. What a great choice! Many people thought I was crazy, but I love the city and would do it again in a heartbeat!


Transition #7 - Coaching

After mentoring at a Chicago-based incubator and with a company providing financial education, I decided coaching was my new calling. So I did some research and signed up for a coaching program.  This completely changed my life. I get so much energy from coaching and thoroughly enjoy the process. How did I know? It was very instinctual.


Transition #8 - Coaching And House Flipping

I moved in with my boyfriend of 7 years. We moved into a house that needs a bit of updating. Oh the challenges we faced. This house has become my part time job for the next year.


Transition #9 (Future) - Living My Best Life

After a year in this house, we plan on moving to different places around the world for a year at a time. I might just start a blog, so stay tuned for more adventure.


I tell you this because I've been there. Moved up the corporate ladder, started a new venture, received severance packages, worked part time while raising my kids, married and divorced, questioned my career, etc,...  


So that leads to who I am and how I work as an entrepreneur coach, career coach, and business coach.


  • Lead with empathy and sometimes a little humor
  • Work hard and will apply that work ethic to your coaching or mentoring needs
  • Will focus on you and your goals
  • Assessments all reflect hyper-achiever tendencies. I lovingly refer to this as a recovering hyper-achiever.
  • Am supportive and non-judgmental, remaining flexible to try different approaches as needed or desired
  • Pattern-finder extraordinaire identifying patterns to help you uncover what might be holding you back
  • Strive for authenticity, remaining true to myself and values, regardless of any outside pressure
  • Act professionally in thoughts and actions, knowing when to speak and when to listen, when to challenge and when to submit, and when to lead and when to be a team player

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