When is theTime to Get Back on the Horse?





How long should we wait after we lose someone we loved?


This is a tricky one and the extremes are tempting. If we just lost the love of our life, it leaves a big old hole in us the size of a giant Sequoia when, after a century, it falls. It can feel like a tooth is missing and our tongue keeps going to where it used to be, searching for that familiar feeling. All we seem to be able to do is go over and over the “why?”of it. Will this ever stop?


The temptation to find someone, anyone to help us stop the pain always looms. We used to call it being “on the rebound”, but whatever it is, filling a hole is not a great way to begin a loving relationship.


Do I wait until I am “healed”, until I don’t feel sad any more, until I “get over him/her”?  Well, if you are 25, that might work. Over 55, you could be dead!


Here is how I look at it…when you feel open to love again, it is time to begin. That might mean wading in. Flirt with someone at a coffee shop, buy a new dress or a soft, stylish shirt that makes you feel sexy, join the gym to lose a few pounds, firm up the abs and begin to get ready for love. Check out a free online dating website...just look, nobody will know.


When you meet someone and decide to go out on a date…ooops!…we call it a “coffee” so it doesn’t feel too serious, treat it like a job interview. If necessary, take a Xanax. Do whatever it takes to care for yourself, realizing that you are one brave creature. You are willing to take the plunge, to feel once again the joy of having someone across the table in the cafe who is a graduate of the School of Heart Hard Knocks.




Thinking you are ready to find someone to share those sunsets and nights by the fire? I’d love to be your guide to loving again.
Call me or email me for a Complimentary Session to learn more about how my plan, Love in 90 Days can get you there with clarity and confidence. 
Donna Bailey, MS
I’m a Coach specializing in Dating and Relationships for Grown-ups
Donna’s Big Red Chair





It’s One of the Hardest Things You’ll Ever Need to Do


This year I’m in a time of great transition. My gut seems to be playing the role of Rudolph, lighting the way in days or parts of days that can feel like a dark woods. It isn’t pleasant and sometimes it leaves me in a heap, having spent the day getting deeper and deeper into a big ball of yarn. What’s the secret sauce? I ask. I beg, I pray. I whine. You see, I don’t like being out of control. I just hate it!


This past year I lost my housing.  Five years ago friends who I adore rented their sweet little condo to me, telling me to  “make it your own”. There was no time limit, so we all thought. Then a year ago they needed to sell it and no amount of wishing could change that. It was time for a new chapter and yet, every time I tried to write it, there were no words. Maybe Stephen King can force himself to meet a deadline, but mine come when they come and no amount of forcing ever works. Same with which direction to go. Looking at a four-way intersection without a marker, not a clue which fork will get me there. It’s like looking at a blank canvas when you’ve got your paints and brushes all ready to go and feeling frozen by “too much white”.


What do we do when we are what I call “neither here nor there”…that state of airless suspended animation, or so it seems? Where nothing is happening and we are crying for the answers. You won’t like the answer and neither do I but here it is…NOTHING. We do nothing. Not because we give up, though we do have to let go of the stranglehold we have on it. You see, what we can’t see, feel or know is that we ARE doing something already. Our unconscious is working night and day. Invisible shifts in our landscape are moving us. And, if we can stop struggling like a woman who thinks she’s drowning in a pool until she puts her feet down and touches bottom…we have a chance to find some peace and serenity.


Answers come, break-ups heal, clarity and solutions mysteriously arrive when we trust. Perhaps we need to just trust our gut, our Higher Power, morning meditation time, our doctors and healers. When we’re lost and there’s no clear way to go, the only answer is doing nothing, waiting for the water to clear and knowing that though it feels like we’re alone, we never really are.  I hope whatever transition you are in this year, that you can let go of the choke-hold that you have on it, trust your gut and remember what worked for you in the past. I’m betting it was a big dose of faith.


Are you tired of struggling and wondering why you can’t find someone to love? Are you ready to look at what’s getting in your way? I’m here to help you see that there is love out there and show you how to find it.

If you’re in a life transition, looking for love, I offer a Complimentary Session

Call me at 510-817-4242 or email me at to schedule a time!


Donna Bailey, MS

Coach, Speaker, Writer and Expert in Dating and Relationships for Grown-ups

Donna’s Big RED Chair



How to Bring the Light Back Into Your Life




Back in 1992 I drove across this big old country of ours, leaving a little village in Maine that had been my home for 13 years. Idyllic, nestled between a chain of pristine lakes, loons calling all summer long, sailboats down at the Yacht Club and friends so dear to me, I thought I’d die without them. Why in God’s name would anyone leave that? Only one thing could have sent me packing to California…light. Or, in this case, the lack of it. Seems my body wasn’t thriving there any more as days got shorter, nights longer and snows that lasted for 6 months made Donna a SAD woman. Seasonal Affective Disorder left me no choice, so in early October I headed to Berkeley.


A friend was my marathon man. He drove us 700 miles a day while I slipped into an exhausted coma. I’d wake just long enough to see the sun rising in Kansas out the front window while the moon was still high in the midwestern sky out the rear window. The salt flats of Utah as we drove down the “World’s Loneliest Highway” created mirages. They were right. It was truly lonely but I couldn’t trust that a semi wasn’t coming ’round the corner when I really needed to pee and there wasn’t as much as a tumbleweed to squat behind.


We made it in 5 days and my driver hero turned right around and headed back home leaving me standing in my friends’ driveway, happy to be in warm sunshine but already overwhelmed by this huge change in my life. Cars creeping along jammed freeways. Where were the loons and peace I had so treasured? What had I done!?


I’d like to say within a week I was sipping lattes and wearing tye-dyed tees. Seems I had traded SAD for sad. I struggled to find work in a place with different priorities and values than New England. My work was less relevant and, a single parent of a fifth grader, I had to earn a living. Things looked very dark, even with the sun shining every day.


I knew I needed help. Truly depressed, so much so that I did the unthinkable (for me). I went to see a psychiatrist and left with a prescription for an antidepressant which I carefully folded up and put in my wallet. Knowing I can hardly tolerate Tylenol, the idea of any meds were terrifying. I had to do it another way and the only thing that had always worked was acupuncture. How I found this particular acupuncturist I can’t recall. Let’s call it a miracle.


Picking my chin up off the floor, I found my way to her office in the trendy, “very Berkeley”area named after trees. Her office was upstairs over the famous Gaia Books and though I had read most every self help book in there, I knew this sadness was beyond me. Finally in the treatment room, she asked me what was going on in my life and all I could do was cry. I told her I’d moved from a beautiful little village of 800 people, 1500 in the five weeks of Maine summer and I was frozen now not from winter, but because of freeways, traffic, noise and the absence of loons and my sweet friends. She smiled and told me something I have never forgotten and that I use to this day when overwhelmed by life. “Just make your world smaller”, she offered.


Jenny was like an emotional Sherpa on my journey from transition-induced depression to finding peace and joy in a new home. She said, “Find a place you love to have coffee each day and just go there. Then, find a park up in the hills with trails you like and just hike those. Go to the same grocery store near your home. Live your life without ever getting on the freeway. Use city streets. Find your places, your people, your favorite sandwich shop and movie theatre. Just make your world very small for now.”


So, as we change our clocks today, let it be a reminder that when in periods of great transition and feeling like we are pulling a refrigerator behind us everywhere we go, we can feel so alone. overwhelmed and sad. I hope you’ll remember what Jenny said to me.When you are feeling powerless, hopeless, fearful and don’t know how you’re going to deal with it all...”just make your world smaller”. Last night I fell asleep, not counting sheep, but one by one saying the names of all the people in my life who love me. It worked for me and perhaps, tonight if you’re struggling, it will work for you.

Feeling the loneliness of the holiday season, and are ready to get yourself out there to find someone to share this next amazing chapter of your life, give me a call at 510-817-4242. I would love to be your guide to finding love again.
May the light grow brighter each day!

Donna Bailey, MS

Coach, Speaker, Writer and Expert in Dating and Relationships for “Grown-ups”

Donna’s Big RED Chair




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