Select Page


Don’t wait for a crisis, a wakeup call, or a more special occasion.  

If you’re an optimist looking for ways to stay positive and rise to the daily challenges of life, this is for YOU. Learn a new way to get happier!  I teach creative calendar skills that make sure you don’t miss out on the good stuff. You’ll be even better at your responsibilities at the same time.

About You

Being your best takes energy.  Where does that energy come from? It comes from your happiness! Every time you’re delighted, or grateful, or do something well, you get a boost.

So it makes sense to build those things into your life directly so you can avoid bitterness and disappointment. It gives you what medical professionals call RESILIENCE – the ability to handle difficulties with less stress.

Everyone will want to know how you do it. You’ll be able to say you just have the habit of Calendaring Happiness… you can see your happiness right on your calendar.


About Calendaring

When you want to make sure you don’t miss something important, you put it on your calendar. Why not do this for happiness?  I’ll show you some creative calendaring skills to make this happen, whether you’re an advanced planner or more spontaneous and looking for a happy day or week. We add a new kind of happiness into the calendar each week.


About Elissa Ashwood


Elissa Ashwood,

Your Happily Ever After Guide

Elissa knows what it’s like to juggle work and life and death, and still find happiness, meaning, and more.  Her work takes the biggest life topics and breaks them down into fun steps that will have you grinning as you take them.

  • Coach and Author.  Elissa has coached clients on work and life from the boardroom to the kitchen sink and back again. Her previous books include Managing Motivation, and Evidence-Based Productivity Improvement.
  • Executive advisor.  As a McKinsey & Co. consultant, VP of Finance at Citibank, Director of Executive Leadership Programs at American Express, CEO of tech company Truly Accomplished and more, Elissa has advised some of the top performing companies and startups in the world to inspire higher performance and satisfaction.
  • Survivor.  Elissa was diagnosed with breast cancer during her first mammogram at 40.  Let’s just say, cancer never knew what hit it.
  • Urban Cowgirl. Living happily ever after in Los Angeles, CA.


Contact Elissa at [email protected]


I speak at selected invited talks.

– on boosting your resilience
– on creating happiness with your calendar
– on increasing engagement in your career and personal development programs

This clip is a bit old, but it was a great event. Picture me a bit rounder and wiser, like Mrs. Santa, and you’ll be caught up.


My most fulfilling moments are seeing changes in people’s lives from the work we do. Since Calendaring Happiness is new, we don’t have client videos up yet, but here are three coaching stories that will give you ideas about how small changes can transform your life. For business stories, visit I am grateful to these earlier clients and still love telling their awesome stories.  I hope they inspire you too.

KARINA: Pro career transition

Karina is such a rockstar.  Enjoy the energy of this fast track pro who made the transition from midlevel to senior exec and brought her personal life with her. Since this video she’s gone on to even bigger roles as textiles innovator, making an impact across industries.

SUZANNE AND AUDREY: Mother and daughter tackle her first career job in NYC

How can a high power mom provide support and also step back so her daughter can grow a career on her own?

Sometimes a little coaching can bridge the gap so the support doesn’t get lost in the mother daughter relationship.

Kudos to Suzanne who went on to run global study programs and is now working from Cambodia!

LINDA: Retiring to the beach
Linda worked her career at IBM, where she experienced huge changes in corporate America. The career she once loved became extremely unpleasant. Early retirement became a matter of health.

She had always done everything by the rules, but dreamed of the freedom to play. Cape Cod, Maine had always been her happy place. She and her husband had brilliantly purchased a beach cottage on Cape Cod and rented it out for decades until now they could finally live in it themselves full time at the beach. We worked to help her find her freedom, have the fun she always wanted, and still have a beach-friendly retirement income.