About Me & You

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Tiffany McLain practicing dental hygiene.


What do you get when you bring together:
A street-smart “kid” from the projects and A conservative “farmgirl”?



Well, me, I guess.


Watching my parents level up was… interesting. In some ways they equipped me mightily for success! In other ways – not so much.

tiffany_02With a generation of poverty, violence and societal racism on one side of the equation and rigid, fundamentalist Christian conservatism on the other, I had a herculean cargo of doubt, insecurity, confusion, and mistrust all combined with a devastating fashion sense.

Being an in-the-flesh product of two extremely opposite worlds led to the feeling that I was an outsider in every situation.

So, I did what any fun-loving misfit does: I became a psychotherapist.

But first, I had to overcome huge external, but more importantly, internal, barriers that kept me from going after the life of freedom that I wanted – for my self, my family and the people who I am stoked to serve. Though the doubts once felt insurmountable, I finally came to learn that battling forces inside could lead to fundamental paradigm shifts – shifts that stand to change the course of one’s life. Thanks to my parents – and tons of psychoanalysis – I’ve discovered:

  • Discipline combined with kindness leads to massive action.
  • Embracing your social moth (or gnat or banana slug) is way more effective than trying to be a social butterfly.
  • Acknowledging your limits will allow you to achieve a life that you never dreamed were possible.

But cool Tweetables are just the beginning. Now, it’s time for the real work to begin.

Sure, you weren’t born with a silver spoon dangling from your lips, but you’re ready to take your innate AWESOMENESS and make your own goddamn spoon. 


  • Maybe you’re here because you love doing social work, but you’re BURNED OUT and can longer give kind, compassionate, loving care to your clients.
  • Maybe you’re here because you want to build your private practice, but you can’t balance your desire to do good and your desire to make bank.
  • Maybe you’re here because you spend all day helping clients with their problems, meanwhile you feel your life is a total shit show. 

Whatever the reason, I make it my mission to show you that you don’t have to give up your soul and be like “this guy” to succeed. Whatever it is that you want to accomplish, if I can do it, then you can certainly do it.

And I promise to tell you about all of the clear, actionable, concrete steps (along with all of the messy, awkward, emotional lessons) that I have taken to get here.

“But Tiffany, why would you do all that?!” 

Because, as I level up, I want Undercover Awkwards – like you – to be standing next to me. Even though I’m a therapist, this site is not about offering you psychotherapy. I love doing one-to-one work, but there are only so many hours in a day and only so many misfits in an hour. In this amazing platform that is the Internets, I can reach out to way more people.

And, unlike in my role as a therapist, I can share with you all my ego-crushing foibles, along with the all of lessons I’ve learned that have helped me move on up. Here are some misconceptions I’ve encountered when speaking with my fellow intelligent, socially responsible, upwardly mobile brothers and sisters:

1 . “Nobody at the top will help me because people at the top are selfish.” 

Says who?! People “at the top” are people just like you and me. Guess what, if I make it to the top, you’re coming with me. There are plenty of people all around you who want you to succeed. Stop your pity party and turn your precious gaze to those who really do want to help you. Then, accept said help. 

2 . “Success means money and money will turn me into a greedy, conservative Republican.”  

If you suddenly become a GCR when you make six-figures, then the reality is, you were a secret Koch operative all along – like the Jason Borne, only more ass-wholish. 

Truth is, money is a tool. If you are able to get more of it, while serving others, then you can use this money in whatever way you want. Your value judgments about people with money are simply defenses that you use to validate your desire to stay comfortable, rather than experiencing the pains that come with growth.

3. “Really helping people means total sacrifice, like working 15 hours a day. In a homeless shelter. While making minimum wage. And living in my mom’s basement.”  

First of all, if your mom lets you live in her basement, lucky you. 

Secondly, from my experience and from the experience of the many people I’ve talked to, this “give it all you got with no thought of your own well being” kind of lifestyle actually leads to huge rates of bitterness and burnout.

There are plenty of ways to help people. Sacrificing your body, mind and spirit ultimately robs you and everyone else of the powerful contribution you could’ve made if you didn’t buy into the martyrdom of “selfless” altruism. There are ways to contribute to society, while also feeling rested, fulfilled, and inspired. 

Buying into the martyrdom mentality is just one more way you keep yourself from taking real risks.  

I’ll leave you with one of the first and most impactful quotes that I had the privilege of encountering: 

“Tiffany, excuses are like assholes. Everybody has one and they all stink.”– My Dad