How to be Sad and Proud at the Same Time

people and relationships. What does all of this success mean if I am alone?!”
I have no idea what my cuddle buddy was thinking as he watched me sob over his essays, but our not-a-relationship didn’t last much longer, and I was left with my grief over another aborted relationship and an even deeper sense of hopelessness about my dating situation.
Here are some things I did after that humiliating and devastating day and that I’d advise anyone to do when they are plagued with a deep sense of sadness about a pain point in their life—personal or professional—coupled with immense pride about other areas of their life:

1. Find and confide in people who understand—even if they are strangers.

As the person above stated, she’s having trouble finding other highly educated single women in which to experience a sense of community as she searches for love as a career woman.
Similarly, a person who’s just been admitted to University of Texas McCombs MBA program with a full scholarship is going to have a hard time finding people to sympathize with his sadness over not getting admitted into Wharton. Most people just won’t get how this guy should have anything to be sad about. He’s going to business school for free. He may even encounter people who feel hostile toward him for being seemingly ungrateful for such an amazing opportunity.
This is where the internet and the gift of anonymity can be immensely helpful. No matter what your particular situation, there is an online forum somewhere where people who will 100% understand and sympathize with your situation.
It may take you some time to find the right online community, but I assure you that with some searching, it exists. It may be a Facebook group, a subreddit on Reddit, or one of those old-school “infinite thread” forums where people are responding to messages across multiple decades.
Make sure you find an online forum or community where snarky, mean comments are downvoted rather than cheered on. For example, Beat the GMAT would be the forum where an applicant who is disappointed at not getting admitted into a Top 10 MBA program would find sympathetic ears. For women who are having dating woes, I suggest the TwoXChromosomes sub-reddit on Reddit. After a few days or weeks of lurking in the forum, create an account.
Some tips: Don’t use your real name nor a username you use commonly across the internet, and don’t post extremely specific details about yourself that make you easily identifiable. Post about your feelings about your situation, ask for sympathy and advice (yes, asking for support and sympathy is an okay and healthy thing to do), and then let the love and support flow in. Make sure not to just dump your feelings on the forum and then disappear. Thank people for their support, answer their clarifying questions, and give them an update if you end up following some of their advice.

2. Let go of the people, places, thoughts, and behaviors that are compounding your sadness—temporarily or permanently.

I know there are lots of people who are big fans of the random hookup, but being intimate without a commitment was making me absolutely miserable and had been for years—so I completely stopped doing it. For my particular situation, dating in general was breaking my heart, so I decided to take an entire year off and let the clock on the “get married by 30” run out so that I could relax and focus on healing from a decade of a stream of unfortunate breakups. During that year, I also focused on what was going well in my life, which was my fast-growing business and my strong female friendships.
Hanging out with people who are school snobs that think that any school besides Harvard / Stanford / Wharton is a waste of time is going to make the MBA applicant I mentioned above feel devalued and discouraged. Don’t hang out with these people—no matter how great the view from their apartment is! Once he’s made up his mind that he’s going to accept that full ride from UT McCombs, it’s time for him to start connecting with his future classmates on Facebook, LinkedIn, and real life. He should be getting pumped up about his future life as a Longhorn. His future classmates people represent his future; those other people devaluing his amazing accomplishment represent the past.

3. Get unapologetically clear on what you want going forward—and what you’ll give up to get it.

We can’t go back in time. My MBA applicant can reply to business school next year if he wants, but he can’t undo his application process from this year. My PhD graduate can’t go back and hire a matchmaker while earning her PhD, and I could not go back and un-date my litany of not-quite-my-boyfriends. But all three of us could have a relentless plan for moving forward with our eyes wide open for what most matters to us in the accomplishment of our personal and professional goals.
For me, that meant making a list of everything I wanted in a partner (it was unsurprisingly long). Once I made the list, one of my friends sat down with me and made me strike out anything on the list that I did not represent myself. I couldn’t expect the man to have six figures in savings, because I certainly didn’t. The list was also a motivating factor for me to be the best me I could be, so that I could attract my ideal partner.
I also created a dating plan in which I outlined what I wanted it to feel like to be in each stage of a relationship—acquaintance, friend, romance (e.g. dates), commitment, intimacy (e.g. sex)—as well as the minimum and maximum amount of time I was willing to stay in a certain stage. For example, I wasn’t willing to spin my wheels in the “romance” category for months upon months without a commitment.
I would advise my PhD sister to do the same and create a list of what she is looking for in a partner as well as a dating plan for herself. She should handwrite the list, and keep it somewhere easily findable so that she can review it periodically, especially as men come into her life. Sometimes, it can be hard to recognize that we’re getting exactly what we asked for if we don’t have a list like that to keep us accountable to accepting what we said we wanted.
I would advise my future McCombs MBA to create a list of what he wants to get out of his business school experience as well as a plan for his job search, social life, and academic life in school. He should figure out what he’s willing to sacrifice to get the kind of MBA experience he wants. One oft-cited point of reference for business school is that you can focus on the job search, your academics, or your social life—two of the three but not all three. I chose to focus on my social life and my classes (at least in my final year anyway) since I realized that I wanted to work for myself after graduation and wanted to take as many classes as possible that would prepare me for this challenge.

Conclusion

Pride and sadness are a frustrating mix of feelings, but you aren’t alone. It’s totally normal if you don’t find many people in your immediate social circle who can’t identify with your feelings. (I was actually very fortunate to have a wide group of female friends from business school who knew exactly how I felt.) The important thing is to find people who do understand your situation, so that you can get your feelings validated. You also have to be willing to separate yourself from any actions, thought patterns, or people who are compounding your sadness, and finally, create a plan for moving forward that doesn’t apologize for what you want but also recognizes that you’ll have to give up some things to get it. For those of you wondering, I actually got my happy ending! I’m now engaged to an awesome guy, and we get married in May! I’m a great example that there’s life after a terrible dating life if you’re willing to give up what isn’t working for you and embrace what is.
I’d love it if you shared an example in the comments of when you’ve been both proud and sad at the same time in your life.

*Note: I would never advise feminine-energy people (regardless of your gender or sexual orientation) to try and convince masculine-energy people to commit to you. This is never a good sign of a strong relationship nor a winning strategy. See the section titled “What to do when he says he doesn’t know what he wants” in my book.