This is going to be very long!
On my 31st birthday, I told my husband I was going to try to "do something" with my writing. I was deep into my finance career by then but had been writing novels on the sly since I was ten years old. And so I gussied up my latest manuscript and shopped it to agents, and finally signed with one about 2.5 years later. She tried to shop that novel but it didn't sell, and so I continued to write. I was fine with the rejection, telling myself "that's okay, I'll just write a better book, and a better book, and a better one after that, and if I'm 85 when my first novel comes out, I'll be very experienced!" I don't remember how many books my agent tried to sell but couldn't (and I told her repeatedly to fire me--she's in this job to make money!) Writing though the angst has ALWAYS been my motto.
Finally, about 2.5 years after I signed with my agent (5 years since my birthday pronouncement), and countless rejections, she sent out yet another manuscript and within 24 hours 5 editors wanted to have it! Hooray! Auction time! Unfortunately, on the day of the auction, one by one, every editor dropped out because I was a "debut author and debut authors are just too hard to sell." Debut authors are very sexy now but in 2010 we were still recovering from the financial meltdown and publishers wanted "sure things." I was devastated, especially because my mantra was no longer apt. How was I ever going to get over that debut author hump?
I had to reassess what I was even doing at that point, especially since my real career (which I loved) was going so well. Shortly after this disappointment, I went to Paris for work. When I came back, my agent forwarded me an article about a woman who died in the south of France. When they went through her estate they discovered she'd had an apartment in Paris she'd locked up and abandoned for seventy years. It was filled, floor to rafters, with unimaginable treasures. My agent thought I could write about this and it became my "first" (ha ha!) novel. When it was acquired by St. Martin's Press they were literally the last publisher that hadn't already rejected it. "A Paris Apartment" came out shortly before my 40th birthday. In other words, 9 years after I declared I'd "do something" with my writing, and 6.5 years after I signed with my agent! It was very quickly a bestseller and shortly thereafter many editors reached out to my agent and said, "why didn't you give me a crack at Michelle Gable?" Uhhh, do you want a list of the books of hers you rejected, including this one!?!?
I should mention that in the middle of all this, I co-wrote a book with a friend, which we sold, and then the publisher decided not to publish it because they were going in a different direction as a company. Also, despite five published novels under my belt, and being a "New York Times bestselling author" the rejection doesn't stop. I have written books my publisher and/or other publishers won't publish. I worked out some of my angst about this in the modern storyline of my upcoming novel "The Bookseller's Secret." (To the point my agent had to tell me to tone it down ;) ). The failure doesn't really stop once you're "successful," it just happens in different ways. It's still difficult, especially as I ended up giving up a career that I loved to focus on writing!