The Brightside: Let's talk about coaching

Hi friends! Happy Friday. Happy SPRING! This week I wrapped up 3 months of coaching with the wonderful Imari, and today’s Brightside is largely a reflection on that time. I am really looking forward to the weekend—Zach and I are celebrating our 2 year (!!) and are going to spend a night at the Rockaway Beach Hotel on Saturday. We’re bringing Louie with us and I can’t wait to watch him lose his mind on the beach, and go to my favoriteeee bakery. Hope you have a great, relaxing weekend ahead.

If you’ve been here for a while, you know I’m a huge advocate of coaching. Last year I worked with a phenomenal career coach, Sheila, and I just wrapped up a three month session of “milestone” coaching with Imari. Both experiences have been immensely impactful. In my opinion, one of the best things you can invest in is yourself—and I’m really glad that I was exposed to coaching in my mid-twenties because it’s helped me figure out who I am, and more importantly, who I’m trying to be.

That said, I get a lot of questions about it whenever I bring it up with friends. The reaction is generally along the lines of: What’s the point? Why are you in coaching, are you ok? I think people hear “coaching” and get a little uncomfortable, which I understand, so I wanted to share my experience with it.

So, what is coaching, and how is it different from therapy?

Disclaimer: There are lots of resources on coaching versus therapy online, which I encourage you to research if you want to learn more. What I’m sharing are my personal thoughts!

Therapy is a place where I go to process. It’s where I explore my thought patterns, talk things out, and understand where certain behaviors are rooted. Therapy has been incredibly helpful and productive for me—and I have stayed with my therapist during both rounds of coaching.

The thing about therapy, though, is that it’s not very “action” oriented—your therapist serves a very specific and important role, but it’s not exactly an accountability partner. Both times I’ve sought out coaching I was looking for someone to do some work with— someone to help me dig deep and create an action plan for change in my life.

You don’t need to be in therapy or have done therapy to do coaching, but for me it was a nice compliment.

How did you find your coaches? Were you actively looking for a coach?

I’ve found both of my coaches through good ole’ fashioned word of mouth. In neither situation was I actively looking for a coach, but I’m always working on myself in some way, and I was open to it in both situations. Honestly, anytime someone tells me that they did XYZ thing and it really helped them grow, learn, or step into themselves more fully, I’m interested.

I was referred to my first coach, Sheila in January-ish of 2020, through one of her previous clients, who was a friend of a friend. It’s actually kind of a crazy story when I think about it—I had this business idea for a Tarot pop-up, so I reached out to this girl who I knew had background in this space. To be honest, I was feeling stuck at work and grasping at straws to do anything to get out of my rut (as you can see by the Tarot business plan)… and when we met up, I was in awe of this girl’s energy and confidence —she was radiant. She was asking me all of these questions like, what are you passionate about, and what drives you… and I was at a loss for how to answer. She mentioned that she had just finished working with a coach, and asked if I wanted to be referred. And I thought hell yes, I want whatever this girl is drinking. And that’s how I met Sheila.

I found Imari in December through a friend’s Instagram post. My friend Lucy was raving about her own recent experience working with him, and I was at a point where I was coming off of Brand Camp. I had all of this energy and momentum for my newsletter, but I knew I needed help sustaining it and creating structure. I also just had this feeling that I needed to connect deeper to my motivation behind The Brightside, and I knew that some coaching would really get me where I needed to be. I also just really wanted a strong start to the year, and we had our intro call on New Year’s Day and the Leo in me just really #loved that.

What do you “work on” during coaching?

The beauty of it is, you can work on whatever you want.

With Sheila, our work was really grounded in confidence building and understanding myself on a deeper level. When I went to her I was feeling really stuck and lost. I felt like I had all of this energy and potential, but I didn’t know how to tap into it, if that makes sense. I felt like whenever I tried to make a change, I would fumble over myself, and I was looking for some strategies to help me be more consistent. What I found out really quickly is that even if you go in for “career” coaching, everything in life is so tied together that you end up doing a lot of “life” work, too.

With Imari, I went in with more specific goals, like to get to the bottom of “why” I do The Brightside, and to get help creating habits to sustain it. One thing I’d say to anyone who is considering coaching is that you really have to be open to what comes up, though—Imari and I boomeranged all over the place from Brightside, to Google, to my life outside of work—you really go deep on what makes you, you. I’ve mentioned this in previous newsletters, but I had some breakdowns, which happen when you are forced to stare at yourself in the mirror and really think about your identity.

It can be kind of intense, but in both cases I have gotten so much clarity on my “path” and left feeling like I was another level more in touch with myself than before. I think if you’re up for the work, you’ll get a lot out of it. But you can’t go in thinking oh, la la, I’ll show up every week and they’ll fix me—that is not what is gonna happen.

What is the *work* like?

Both coaches I’ve worked with have used some sort of exercise component (either during or in between sessions) like journaling prompts, personality tests, meditations, reflections, schedule building—you name it, and we’d talk about them in depth during sessions. In both cases I found that all of the work really builds on itself, and as someone who already really likes introspection I had a lot of fun with it (even though, like I said some tough stuff DOES surface!!)

How about structure?

With Sheila, we met every few weeks for a few months and with Imari it was a bit more structured: a 3 month contract, where we met every week for 90 minutes, with a 15 minute “check in” in-between. It was like a life bootcamp. I think both approaches are great, and both worked for me.

Biggest Takeaways

Oh man, I feel like this list could be a million miles long, but I would say my biggest, most profound takeaways from coaching have been:

• Confidence: I feel much more strong, secure, and aware of who I am. It is so much easier to show up as my full self every day; or understand that when I’m not showing up as my full self, I should probably pause and investigate what’s going on.

• Ability to advocate for myself:I think because of the confidence, I am just better equipped to advocate for myself or express my needs, which I always had a tough time with.

• Increased Awareness: of who I am, who I want to show up as every day, what motivates me, why I work

• A better relationship with myself!! Both experiences have really helped me find self-compassion, which I just think is so, so important - and again, really challenging sometimes - especially if you are prone to negative self talk, which I certainly am.

• Self-Trust: I can pinpoint specific things in my life that I would NOT have tried if it wasn’t for coaching. But becasue of the confidence I built and the deeper understanding I had of who I was as a person, I raised my hands for projects at work, I kept working on The Brightside that I might have otherwise felt insecure about (good ole imposter syndrom, eh??). Something that Sheila really instilled in me was that if your desire to do something was coming from a good place, or your heart - then you shouldn’t hold yourself back. And Imari really tought me how to identify the “fear” voice in your head but know that whatever it was saying wasn’t true.

I could go on and on, but the last big thing I’d say is clarity on my “path”. I think before coaching, both times, my head was just spinning in a million different directions, and that was always really tough. I never knew what I should be prioritizing or showing up for - and when you really get to the bottom of who you are and what motivates you, the rest becomes a lot more clear.

From top: Got DRESSED!!!, Pastries from our favorite coffee shop down the street (yes, that's an everything croissant stuffed with ricotta), flowers from said coffee shop (the owner goes into the flower district every week and makes the most INCREDIBLE flower arrangements), and a good ole fashioned mirror selfie.

I will probably be purchasing another pair of Tkees. Although I just got my first pair a few days ago, Louie chewed them up within 24 hours of their arrival. SIGH.

• Did anyone ever watch the Andy Milonakis show? I think about the theme song more often than I probably should, and it holds up.

• I REALLY wish I got to see In The Heights on Broadway, but I CAN’T WAIT to see the movie. This trailer!

• Speaking of movies, Zach and I committed and watched Interstellar this past Sunday. Warning: do not watch if you’re prone to daydreaming about pixie cuts.

• Ok, this is random - but I just got Zach and me phone stands for our desks, and they’ve been a GAME CHANGER. Best WFH office optimization yet.

• And lastly - I’m cooking up a website for The Brightside! I am really committing to it and building something cool on WebFlow - I was hoping to have it ready to send out today, but stay tuned for something in the next Brightside. I can’t wait to share!!