Earlier this week, I tried using Adobe Illustrator for the first time in my life to take a stab at creating an illustration for my children’s book.

Truth Nugget: When I was a kid, I figured out how to make animated buddy icons on Photoshop for AOL Instant Messenger. To this day, I have no idea how I did it. I don’t even know what file extension allows for animations. AND you guys, those were before the days of YouTube tutorials. I’m pretty sure this was before even Google. Middle-school-me was awesome.

Truth Nugget #2: It JUST occurred to me that we call the very well-known animated super short movie and tv clips gifs because they’re probably saved as .gif’s. Face palm.

Oh, what a digresser I am.

Okay, so I started to feel my energy level fall, but I ignored it because I was so freakin’ committed to creating a first illustration. All was decently well until I started to create the protagonist – a kid named Petunia. Because I was using a tool I had no idea how to freakin’ use, I probably spent 1 hour on the classroom setting and another 3 hours on Petunia alone. She turned into a really weird looking adult… and with no legs because at some point, I gave up. (Picture at the end of the post.) Instead of finishing the page of the book, I wanted to sprawl onto the floor into the fetal position. Because, after my one-track mind was able to come back to reality, I realized how wrought I was with exhaustion. My mind hurt.

But damn it, you guys. The truth is that I should have stopped the moment I felt myself starting to burn out. I should have stopped because the burn out overflowed into the next day. And that next day? Well, it sucked.

Loneliness set in.

From the moment I woke up, so many horrible things started to occur to me. Namely, how my phone hasn’t lit up for what felt like forever. It’s been radio silent. Do I actually have anyone in my life?

Normally, I would have been pretty rational about this.

Annie, it’s not that you’re not important. It’s just that people have very busy lives. If you need them, they’ll be there. Just tell them.

Annie, you have so many people who care about you. You once felt so grateful for the people in your life that you already started a wedding invite list with them on it. Them: the people you want to share the happiest moment of your life with because you know how happy your happiness makes them.

ANNIE, you’re not even dating anyone and you’re already planning a wedding around the people you can’t wait to sit there with you in that wedding venue.

But loneliness is a cold, spiky beast that seems to suck all the rationality out of you. It takes the color out the room and puts a heavy weight on your heart. The only thing you know how to do is feel sad that no one really cares, and it occurs to you that you really have no control over this. None. Loneliness is a beast that makes you watch all the episodes of This is Us and A Million Little Things because you want to drown in your sorrow and just cry.

And I did cry. A lot.

I wasn’t entirely taken by the beast. I was above the surface just enough to want to get out of this feeling; to try everything everything I could to get some color into my life again.

  1. I laid there on the couch. (Because sometimes your body is just exhausted, and it needs you to let it get that exhaustion out of your system.)
  2. I binge watched sad movies. (Because sometimes you just have to allow yourself to feel whatever it is you’re feeling without judging yourself.)
  3. I let myself cry. (Because sometimes your entire Being feels lighter after you’ve had a really good cry session.)
  4. I forced myself to start a guided meditation on my Insight Timer app. (Because sometimes your brain needs some literal help to stop ruminating on the current bad times.)
  5. I let myself fall asleep during the aforementioned guided meditation. (Because again, my body probably needs the shut eye so you know what? I’m going to let it be okay.)

Nothing worked. Historically, one of those things would have always worked for me. Always. But not this time. I needed this heavy feeling to go away. God, I needed it to go away. So, I went for a run. (I haven’t really worked out in about 1.5 years, but you know, desperate times.)

That didn’t do the job either.

My mind just kept thinking about how silent my phone has been: all the people in my life who don’t make an initiative; how many people I have to make plans with for there to be any plans at all; people I consider my best friends. And these thoughts were eating me alive. Alive.

I was so in my head.

I felt so alone. I had just moved to this city a few months back and had no safe haven to flee to. I genuinely felt like I had no one to call. That no one would understand. That there was no one who could help me get me out of this bad feeling.

But I was desperate, so I reached out to two of my friends.

Friends 1 and 2

To friend #1, I made it sound like it wasn’t that serious. I couldn’t allow myself to let my guard down with this one. I was too scared. Too ashamed about this level of darkness I was feeling. I did tell him that entrepreneurship loneliness hit me hard and that it was a real thing. That I know ‘cause I googled it. He texted me for a bit and then fell off the face of the earth or something.

Deep breath, Annie.

To friend #2, who is an entrepreneur himself, I laid there on the couch and lightly begged through the phone’s speaker, “Can you tell me again about your hard days as an entrepreneur? How you felt lonely and like you had no one too?”

I needed someone to remind me that it’s not just me.

He briefly expressed how he felt it too and dished out some tough love thinking that would help me out of it. In a nutshell, he said, “You gotta just get up and do the work.” And then he said he needed to get back to work.

Well, obviously that didn’t help either.

Honestly, I don’t know why I tried to talk to my two GUY friends about this.

What I really needed was for someone to not think they know what’s best for me, dish it out and then leave it at that. I needed someone to ask me, “Did that help?” And if I say, “Not really,” for them to stick around and try something else. For someone to not make me feel like I was inconveniencing them. Because my wellbeing is worth that much to them.

And because trust me, there is always, always a way to get someone even an inch out of the muddy blues. I know because I’ve been there for my friends many a time. Many. A. Time. And I’ve stuck around until the black, spiky sadness bug budged even a tiny morsel. I didn’t give up on my friends.

Truth Nugget: Hindsight is 2020 and really, what kinds of friends are cold enough to be friend #1 and friend #2?! What kind of company do I keep?!

Friend #3 (the one who actually helped)

Later that day, I called one more friend. She empathized with me. She didn’t judge me in my worst of times. She didn’t just tell me what to do. She just felt with me. She was so incredibly present in these moments with me. She just listened.

There’s something so powerful about someone hearing what your mind is going through in your absolute worst of times and them still loving you all the same. It lightens even the heaviest burdens.

It heals.

After a good amount of time of her being there with me, while I was at my worst, I felt heard and accepted. And I felt like my bad times aren’t as awful as I thought because here is my friend loving me anyway. So, I felt a bit lighter.

She then suggested that I try volunteering. BUT she offered the advice as a suggestion to “try on”. Did you get that? She did not GIVE advice. She offered it. She didn’t tell me I needed to do something; she lead with “would you consider/do you think it would help to…” This is so important.

Annie, you love people. She told me. You love people and you love doing things for others. You’re missing this right now. Have you considered volunteering at all for a few hours a week? I think it’d be exactly the dose of people you need.

And then, I “tried on” the volunteering. Does this fit, Annie?  I asked myself.


The truth is, I told her, I had considered this but never put the pedal to the metal to actually find someplace to volunteer. I don’t know where to start right now.

Email my friend and tell him you’d love to volunteer for his studio, she said. Honestly, they always need more volunteers. And you can be totally honest with him, Annie. He’ll understand. Tell him you just moved here and you also just quit your job and you’re in a bit of a rut because you need some good people in your city. He’s good people.

Thank God for friend #3. That’s what I needed. While she was on the phone with me, I got on my computer, opened up a new email, and already started writing in it.

I understand now.

I understand that when anyone is feeling that low, they need three things.

  1. For you to listen, truly listen, with no judgment at all. Allow your friends to let out their pain and negative feelings. And when they feel icky because they hate the down-in-the-dumps person they’re being at the moment, make sure they know that you love them anyway.
  2. For you to not give, but offer them advice. One of the keys to helping a person out of a rut is helping them realize on their own how helpful something would be. If you offer a solution, they can mentally try it on and see how it feels for them.
  3. And if 1 and 2 doesn’t do the job on their own, they may need you to give them a stick. More on that in a second.

Truth Nugget: Most people miss #2 entirely and just tell people what they need to do. I needed to get out of quicksand, but it wasn’t going to help for anyone to tell me that I needed to do X, Y, or Z when I was still stuck. Why? Because sometimes innocent advice reminds me how I’m not mentally in a place to do what is suggested and I start squirming wishing I was. And then BAM, I sink further.

But friend #3, when she offered her advice, I didn’t feel the pressure of needing to be a certain way. I could try suggestions on and see what would work without feeling worse if something didn’t. And then when she gave me a stick, I could see above the sand a little bit again.

What is a stick in this case? It’s basically spoonfeeding someone something so that they can regain some of the control they feel they’ve lost entirely.

  1. Don’t tell them to find volunteering opportunities. If they’re truly open to the idea, look some up for them and tell them exactly which to apply to. (It’ll take you 5 minutes.) Maybe even show up at their place or straight up call them to help them fill out the application in real-time with you. Or do what friend #3 did and tell them exactly who to email and what to write.
  2. Don’t just tell them to read a book. If they feel like it might help to read, buy them the perfect escape of an e-book and get it emailed to them so they can start it right away.
  3. Don’t just tell them to go get some dinner. If they are hungry, do the unexpected thing and make reservations for them. Or better yet, show up at their place with wings. Or sushi. Or you know what? Both. Then get yourself an award for being the best friend of the year.
  4. And whatever you do, do not tell them to “relax” or “get to work” or “get over it” or “be positive.” Never do anything like that. ‘CAUSE SPOILER ALERT: THEY WANT TO RELAX. THEY WANT TO GET OVER IT. THEY WISH THEY COULD GET TO WORK. THEY WANT TO BE POSITIVE. And they’re obviously having a hard time with it right now otherwise they wouldn’t have reached out!

In general, if you’re stuck, it’s always a good idea to ask how you can help.

How can I help you? This question is extremely thoughtful and kind. It shows that you care more about them and what they need rather than whatever perception or view you have based on who you are. The question also might help them begin to understand what it is THEY’VE been missing that CAUSED the darkness in the first place. But on the off chance that they don’t know how you can help, tell them it’s okay. Tell them they can feel shitty and that you’ll sit there with them for as long as you need if that helps them.

Truth Nugget: If you’re reading this thinking, “God, I don’t have time to sit with someone for as long as they need,” then I’m sorry to say, you’re a crappy friend. Someone you apparently care about is tipping into some form of blackhole-like depression and you can’t find the time to help them breathe easier? First of all, it’ll probably end up taking 15-20 minutes MAX of your time if you’re fully present with them, and second of all, shame on you. It’s crappy friends like you that make people think they burden everyone.

Oh, man, that was mean. Sorry… I guess I’m pretty passionate about this. Anyway, I digress. As usual.


After listening without judgment, loving them anyway, and offering them suggestions, throw them a stick. Don’t give them more to do when they’re trying so hard to just feel okay. Give them one less thing to do. Just one less.

And that, my friends, was my first bout of entrepreneurship loneliness. Emphasis on “first”.

Can you relate?

With Love,

Exhibit A that I should do everyone a favor and not be my own illustrator. Poor girl looks like a chuckie doll with a mullet.

The Protector Meets Awesomeness
The Honeymoon Phase is Over