My suggestion is double-edged:
On the one hand, it might help to find out just WHY you've got this low self-esteem (when everything seems to be going your way). In my own case, it was largely due to
a) my father's continuingly telling me that I didn't match up to my [eight year elder] brother. ("Why, at your age he was so much more responsible than you! I could have dropped him off at the corner and by the time I'd found a place to park, he'd have bought half the items on this list. With you, I have to drag you into every single store myself...")
b) my eldest sister's continuingly telling me that I broke everything I touched.
c) the Church telling me (continuingly) that I was basically an oozing bag of filth, and that it was a miracle beyond human understanding how God could possibly love such a scumbag.
Often we have low self-esteem because somebody has drummed into us what losers we are. It might help to realise that the kind of people who spend their time putting other people (us) down are usually pretty fucked up themselves and turn their own self-loathing into attacks on / criticisms of others.
The second part of my advice I now copy-and-paste from another thread
that I posted it on. This one seems a good home for it. Bear in mind that the individual details need to be tailored to each person's own situation / capabilities / strengths. It's almost 3am, I got just a few minutes sleep LAST night, and I haven't got the energy / time right now to modify it into general terms:
I had a MASSIVE inferiority complex when I was a child and adolescent. I'm going to give you my self-therapy tip and ask you to try it out:
Look at yourself in a good-sized mirror. Look into your eyes and tell yourself:
a) I'm an attractive woman.
b) (More important) I'm a good person.
c) I have friends who do really care for me.
d) I have a supportive husband who loves me (and loved me when I was "OBESE") and a son who thinks the world of me.
e) I'm an excellent ---. [In my case it was ... babysitter and the maker of the best pizzas I know. (I have now graduated to "the best babysitter I know", as well.)]
f) I'm intelligent and caring.
g) If anybody else has problems accepting me as I am and/or seeing my worth... well that's their problem - not mine - because my worth is plain to see to anyone who (as the Little Prince' Fox said) "sees with the heart".
My therapy is free, it works (even if you can't help laughing at yourself during the first few sessions)... and it'll drive your husband crazy, wondering what you're doing for so long locked in the bathroom.
I hope that that helps. If you click on that link, you'll find that Ivy DID feel silly trying it... but that it did help.
It doesn't even matter if you have a sneaking suspicion that those nice things you're saying to yourself are lies. Hearing them helps... and works the miracle that they stop being lies (self-fulfilling prophesy).
[It actually took me years to really feel good about myself... but mine was a pretty extreme case.]