Ali on the Run Show Episode 57: Date Night with Ali & Brian, Talking Dreams, Goals, Fear, & Failure

“I went on this amazing trip, and I thought everything would change. But your problems don’t just go away because you run away. They will follow you anywhere until you fix them.”

This episode got a little heavy. Last Friday night, over a bottle of Pinot Grigio, Brian and I sat down to catch up, since it’s been just about a month since my life-changing “CAli on the Run” trip. What started out as a conversation about learning to be more present turned into the most honest, most scared, and most raw I’ve ever been on this show or to anyone but Brian (in private!). This episode is on the heavier side for me (and please ignore my stuffy nose — I’ve had a cold for a week straight!), and I debated even releasing it. But why not do something that feels a little scary? And scary, right now, is sharing all this brutal honesty with the world. So here we go! (Plus, listener Q&A!)

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Here’s what you’ll get in this episode:

  • “The Story of Last Monday” & lessons on being present (3:00)
  • All about the amazing gift I gave Brian for his birthday — and why he returned it (10:00)
  • What it really means to be Ali on the Run lately (11:40)
  • “I don’t know what I wanna be when I grow up” (16:10)
  • Ali starts to cry (21:13)
  • “What are you curious about?” (25:30)
  • On success, and what it meant growing up vs. what it means now (30:40)
  • Ali cries again (31:10)
  • Fear and failure (32:15)
  • The single biggest challenge in our marriage right now (39:00)
  • On inspiration (45:40)
  • Brian reflects on his dad’s legacy (52:00)
  • Listener Q&A (56:50)

What We Mention on this Episode:

CAli on the Run: My 7-Day Pacific Coast Highway Road Trip Itinerary

“Making It Count”

Ali’s Bermuda trip

Orangetheory Fitness

Dance Spirit

Mia Michaels on Episode 35 of the Ali on the Run Show

Ali’s New Year’s Resolutions

Brian on Episode 2 of the Ali on the Run Show

Brian on Episode 17 of the Ali on the Run Show

Brian on Episode 47 of the Ali on the Run Show

Brian on Episode 52 of the Ali on the Run Show

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22 Responses

  1. Ali – I can’t even begin to explain how much I related to this episode. I really appreciated the back and forth between you and Brian too because it prompted me to ask myself those questions too and to actually think about the answers. You should check out the Clarity on Fire site. They have some great resources and the blog is basically one long reminder that you’re not alone when it comes to questioning “what’s next?” Anyway, thank you for never being afraid to keep it real and to be vulnerable. I love “hanging out” with you every week!

  2. Loved loved loved the honesty and vulnerability. You are a hero! I can see how that would be really challenging to your relationship, especially when you’re sick! So sick and totally out of your control, while your husband is being his absolute best self. I feel at opposite ends of the spectrum with my boyfriend a lot and it’s frustrating. I don’t really have much advice for you, but I do think you should give yourself freedom and space to explore your passions, whatever they may be. I insta-stalked your husband and it would appear?? that he’s making enough money for you to be financially stable. I’d try to see that as a blessing and as an opportunity for you to really go after those little things you enjoy–talking to people, bringing dogs to children’s hospitals, etc! Be your fabulous self and you’ll end up where you’re meant to! I think abundance shows up in different ways…you don’t need to be bringing in a ton of money from a “real job” to bring worth into a relationship. I think sometimes it’s better to bring your full, passionate, best self into a relationship, however that shows up for you. Best of luck and thanks again for the great podcast.

  3. Ali – this is absolutely the best podcast yet. Thank you so much for being so open and willing to let honest pour through. Your spirit is contagious.

  4. I’m a new listener, and I caught this episode while setting up for my kids’ third birthday party. I, like you, am a self-proclaimed people pleaser who cannot stand to fail. At anything. Even something as “stupid” as the Daniel Tiger trolley I tried to “build” my kids for their party. I, like you, had lofty career aspirations that ultimately turned into “WTF am I doing?” at a company I couldn’t stand and couldn’t seem to get out of. I’ve stayed at home with my kids the last two years with the intent of starting a freelance editing business and parenting website so I don’t have to re-enter the workforce when the kids hit school age, but I’m dragging my heels. I don’t want to figure out all the intricacies of each on my own — I want someone to do the work for me and tell me what to do so I don’t do it “wrong.” I just wanted to let you know that you’re not alone in your feelings, and I hope you were able to find some clarity and direction with Brian. I hope you’ll continue to let us have glimpses of your journey.

  5. Thank you so much for sharing this! You may not be at a place in your life where you feel very confident, but it takes a confident person to share a podcast where you allow yourself to be that vulnerable. I totally feel you on the financial security thing, my dad was the same way and that has definitely affected how I view work / making income / taking risks. You said (I think?) that you didn’t know if this would help anyone.. well it helped me!! I am totally not one for “revelations” but I was listening to this on my run and something the two of you said made me realize the direction I at least want to try and take my career, something I’ve been thinking about for many months now. SO THANK YOU 🙂

    “Also screw that person who said you didn’t have a job because you shifted to freelancing.” << this! Doing non-traditional work is hard and scary and in no way not a job. I'm sure you already know that person's comment made no sense, but just another bit of reinforcement here.

    Not sure if this would work for you or if you're already doing it, but sometimes setting a goal that requires a bit of daily work but is not ridiculously out of reach can help to build confidence back up (like maybe not just running, but training for a race if you feel you're physically and mentally ready to tackle something like that). By the way, congrats on your running in Bermuda – those are some pretty sweet paces back to back on no training! And

  6. I love what the previous poster says (seriously) and I have virtually the opposite ‘suggestion’ . ha! I was “blessed” to stay at home for the last 6 years with my young kids but for most of it I was lonely AF and desperate to go back to work. Its a long story but I FINALLY went back a few weeks ago and while I don’t love it, i do LOVE being with people. Sometimes a 9-5 *IS* a good thing. Sometimes being content with work is good enough if you’re around the right people. It sounds to me like you’re kind of lonely (maybe i’m projecting… who knows) . I know you love your dog but I think regular human social interaction is really important and sometimes we just need the regularity of a job to insure that we get it. You can continue to ‘fill your bucket’ so to speak with the podcast (which I love!) and maybe just a few of the freelance jobs you really are passionate about.

  7. Great episode. Brian does a great job drilling down his questions to get to the root of the issues. Many of the things you discuss are very mirroring to my life (except I was never as driven as you in terms of a career), but similarly, I had a goal, I met that goal and after it was met, I was a bit disappointed because it wasn’t enough or it no longer served the desire I once had for it. But that’s what growing as a person is about and it’s hard, especially if you had such intense feelings about something at one point and then they dissipated. It’s funny you talk about wanting to be in the moment. I’m reading Silence by Thich Nhat Hanh which addresses “The Power of Quiet in a Word Full of Noise.” Simple read but really effective if you practice it. It’s about getting back to basics and finding that spark, which I think you already found when you talked about what really makes you excited (talking to people, learning their lives, etc.) You could really capitalize on that and make a career out of it. At some point (soon) you have to stop blaming the way you were raised as a reason for not being able to get over your preconceptions about conventional jobs and how money is made. I used to feel the same way – need an employer, a 9-5 job with benefits, etc., blah, blah and all the while I watch examples upon examples of people who have quit their “real” jobs b/c their blogs were taking off and they were now making 6 figures writing about stuff that got them excited. People make a lot of money (or at least a decent living) doing things that are unconventional. The very things you talked about in this podcast are the same issues that so many people deal with and want to hear about. Look at Humans of New York – people love that because it’s relatable and heart wrenching and inspiring. And that person who told you you weren’t relatable anymore b/c you no longer have a 9-5 job is maybe stuck in the same limiting thought pattern as you are. Things get stale if they don’t change and morph. You’re bound to lose and gain readership/clients/etc. because it’s human nature to ebb and flow. It’s not a personal assault. If you’re worried about people being disappointed in you for failing at something you try, I imagine that they would be even more disappointed in you if you don’t try at all. Your heart know what makes it happy. You can craft a career around that very thing. Thanks for your honesty and connecting with us folks.

  8. Thanks for sharing, it is nice to hear someone talk about their struggles as they are experiencing them. Rather than after the fact, when all the loose ends are tied to tightly in a neat bow. I found this very relatable and appreciate your vulnerability. From what I know of you reading your blog for the past years, whatever you set your mind to you will achieve. Love your podcast, keep it coming!

  9. Just wanted to say thanks for this! Recently, I quit my job that I loved with people that I love because I was feeling too comfortable. I was feeling like I was the one with the answers rather than the one asking the questions. I’ve joined a company that is really challenging and this afternoon I am giving a presentation to folks who are MUCH smarter than I am. Your discussion about putting yourself in rooms where you are not the smartest in the room will definitely be me today! Listened to this on my ride in to work this morning and will be my inspiration during my presentation!

  10. Cannot wait to listen to this on my commute home!

    “Dreams, goals, fear and failure” just about sums up my life’s worries right now.

  11. Just curious if you’ve thought about going back to school? I think you would be a fantastic mental health professional, whether it’s counselor, therapist, psychologist, etc. You understand the important connection between mind/body. You’d get to spend all day talking to people! It’s a job!!

    And it doesn’t have to be a specific like office-hours kind of job. It could be something like how life coaches work.

    The way you talk about mental health, between this podcast, your podcasts with Mia Michaels and Andrea Barber – I mean. You get it!

    Anyway, I hope you figure all of this out. You’re awesom. ❤️

  12. You are awesome! About 36 minutes in you talk about expectations and how you process them. Are you familiar with the 4 tendencies (getting some buzz on career podcasts)? It is all about how people respond to expectations: outer expectations and inner expectations. The author released a book about this that might interest you as you kick ass on your journey. “4 Tendencies: The Indispensable Personality Profiles That Reveal How to Make Your Life Better (and Other People’s Lives Better, Too).” Also screw that person who said you didn’t have a job because you shifted to freelancing. That involves a lot of hustle!

  13. Really excited to listen to this episode. I’ve been enjoying your podcast episodes so much, Ali! Thanks for sharing your life, friends, and colleagues with us.

  14. Currently listening to this and it’s like you’re talking right to me. I got a PhD in Biochemistry and am in a soul sucking job that I realize I do not want to be in. Honestly don’t even really wanna do science anymore…but then that’s failing, right? What the hell did I get a PhD for? What will my friends and family think? Gahhhhh I’m so right where you are right now. Thank you so much for voicing this for me today (because obviously this is just for me lol).

  15. “But your problems don’t just go away because you run away. They will follow you anywhere until you fix them.”

    That feeling to just…get away from the day-to-day (and bigger) problems is totally familiar. I do think there is some value in taking a break from them. It can be helpful to take a break from the stress of trying to figure them out and fix them. Sometimes, that time away from them helps me approach them with a clearer, less frustrated mind.

    Anyway, I need to print this out and hang it on every wall in my condo. And thank you for sharing this episode. As a fellow 30-something-with-a-chronic-autoimmune-disease, I appreciate the discussion.

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about ali

I’m the creator of the Ali on the Run blog and the host of the Ali on the Run Show podcast. I’m also a freelance writer and editor, a race announcer, a runner and marathoner, a mom, and a huge fan of Peanut M&Ms, Mamma Mia! Here We Go Again (way better than the first one!), and reliving my glory days as a competition dancer in the early 2000s. I’m really happy you’re here.
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