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307: Overcoming Self-Doubt and Embracing Unexpected Obstacles

Have you ever let nerves or setbacks stop you from reaching your next big goal?

In this solo episode of the Happier at Work podcast, Aoife O’Brien offers an honest, behind-the-scenes look at her US book tour for “Thriving Talent.” Broadcasting from San Francisco, Aoife shares both the exciting highlights and the unseen struggles of traveling alone, everything from logistical headaches and moments of isolation to being featured in Forbes. She dives into a personal story about overcoming her hesitation to drive in the US again, using the metaphor of navigating challenging roads (literally and figuratively) for the kinds of setbacks we all encounter in our careers.

In This Episode, You’ll Discover:

  • The reality behind high-visibility work, and what social media doesn’t show about travel, loneliness, and logistical challenges.
  • How nervousness and setbacks can signal growth opportunities and what to do when you want to give up.
  • Practical encouragement to reflect on your own barriers at work.

Related Topics Covered:

Overcoming Challenges, Confidence at Work, self-doubt

Connect with Aoife O’Brien | Host of Happier at Work®:

  • Website
  • LinkedIn
  • YouTube

Related Episodes You’ll Love:

Episode 300: How Great Leaders Build Thriving Teams with Bhushan Sethi

About Happier at Work®

Happier at Work® is the podcast for business leaders who want to create meaningful, human-centric workplaces. Hosted by Aoife O’Brien, the show explores leadership, career clarity, imposter syndrome, workplace culture, and employee engagement — helping you and your team thrive.

If you enjoy podcasts like WorkLife with Adam Grant, The Happiness Lab, or Squiggly Careers, you’ll love Happier at Work®.

Editing by Amanda Fitzgerald.

Website: https://happieratwork.ie LinkedIn: https://www.linkedin.com/in/aoifemobrien/ YouTube: https://www.youtube.com/@HappierAtWorkHQ

Mentioned in this episode:

Thriving Talent book – out now

Book

Aoife O’Brien [00:00:01]:

Hello and greetings from San Francisco, which is where I’m recording this podcast episode. If you’ve been following along on social media, you will see that I’m doing a book tour in the US at the moment. So I started in New York and you may have heard episode 300 of the podcast which we recorded live in New York as part of my US book launch for my book Thriving Talent. And the next stop on on my city tour was Boston, and I met with a wonderful company there. They ordered some books, I spoke about the book and I answered questions from leaders there. So from the outside, what you might be seeing on social media is, you know, these features, me traveling around with the book and actually at the time of recording, I just found out this morning that I’ve been featured in Forbes as well, which is really incredible, a total pinch me moment. But what you don’t see is the behind the scenes activities.

Aoife O’Brien [00:01:03]:

So I’m here on my own. It can get quite lonely. There have been issues with travel, with booking flights, with making sure everything is coordinated, with getting things to the right places on time, with setting up meetings, like all of the behind the scenes stuff. And it’s, it’s lonely and it can be quite exhausting as well. I’ll be brutally honest. And anyone who’s speaking to me at this stage of the tour, which, you know, I’m already four weeks in, I’ve got another week and a half or so left of this tour. I’m in San Francisco now, I’ll be going to LA next. And I’ve also been to, as I mentioned, New York, Boston, but Chicago, Austin, Seattle, Portland.

Aoife O’Brien [00:01:43]:

I’m in San Francisco and finishing the trip in LA. And if anyone asks me now, I’m like, it is too long. It’s five and a half weeks in total and it has been exhausting. So if you hear me talking about another trip to the us, do feel free to remind me that I should do either east coast or, or west coast or Midwest, south region and not try and do everything all at the same time. It’s typical me fashion, I might say today’s episode. I wanted to share something that happened just yesterday. And without sounding too cliche, it was, you know, it was something that really resonated with me, something that really struck a chord. For the stuff I talk about and me being human, I’m impacted by this stuff as well.

Aoife O’Brien [00:02:26]:

So yesterday I’d been putting it off for a while, but I wanted to rent a car in San Francisco. So Monday evening I went and I Reserved a car. I went yesterday morning to the hire car place and I got my car. I was feeling really nervous about it. I have driven in the US Before. I have driven on the opposite side of the road before. But for some reason, my body was really reacting, and I was so, so nervous about driving on the other side of the road. And I was thinking about younger aoife, you know, 12, 13, 14, 14 years ago when I did this, I don’t remember feeling this.

Aoife O’Brien [00:03:03]:

Maybe I did, and I just don’t remember. Maybe my body is reacting. But what happened was this. I went along and I got the car. And obviously they did the whole, oh, this is the car you reserved, but there’s another amazing car over here. And because of the state I was in, I just went with it. I was like, okay, yeah, let’s upgrade the car. Let’s get a better one.

Aoife O’Brien [00:03:20]:

To be honest, it suited me better. I’ll get to that in a second. When I went to pay for the car, the first card was declined. Okay, we’ll try it again. Second card was declined. Okay, new card. Card declined. New card, card declined.

Aoife O’Brien [00:03:33]:

And with every fiber of my being, I was like, this is not meant to be. I am just gonna call it quits. This is the universe’s sign. And I have meetings scheduled with people. So I booked the car. Didn’t realize just kind of how grand the Bay Area was. So I booked a car to go to Silicon Valley, around Menlo Park, Mountain View, all of that kind of area, and then down to Santa Cruz as well to meet up with people. But every fiber of my being was like, don’t do this.

Aoife O’Brien [00:04:02]:

Just switch to zoom. And I suppose it was my body’s way of saying, you’re not confident to do this, so who do you think you are? And all of those kinds of things. All of these messages that I talk about all the time. I moved around a couple of things, and in the end, I was able to use my Revolut card to pay. And it worked. And so I had the car and I started driving and I did it. And I was nervous the whole time. And I kept thinking, this is, you know, it’s nerve wracking.

Aoife O’Brien [00:04:32]:

This is how people feel all the time. Maybe you can’t relate specifically to the car, but, you know, we’ll talk about that in a second. You know, maybe it means something else to you. But when I was saying earlier, by upgrading the car, I had access to maps, so that was a fantastic tool that I had. I didn’t have to rely on looking down on my phone, taking my eyes off the road, which I definitely didn’t want to do. I definitely was gripping that steering wheel really tightly. And if you’ve ever been in that neck of the woods, and I certainly hadn’t, but if you’ve ever been in that neck of the woods and you know the stories that people were telling me, it’s a windy mountain road. I didn’t realize.

Aoife O’Brien [00:05:11]:

Now, I pictured windy mountain road as something that you might find in Ireland where only one carp can pass, but actually it’s two lanes each way, and it’s just that the locals drive super quickly, and so you feel like everyone is going fast and they overtake you. And it is quite windy and it is on a mountain. So you kind of go over this mountain to get to Santa Cruz. I won’t say that I wasn’t nervous. I was still nervous the whole time. I was too nervous even to put on music in the car. I could have listened to a podcast, an audiobook, put on some Spotify tunes, and I just thought, I just don’t want any distractions whatsoever. I want to focus on being on the road.

Aoife O’Brien [00:05:46]:

So that’s my story from yesterday. Generally, what I found is the reception. In the US People have been so open to meeting up. Even if I’ve never met them before, even if I’ve literally just connected with them on LinkedIn, even if we’ve just met in person, they’re so open to being helpful. I will say any Irish people who have had that level of support themselves when they first arrived in the US are so open to helping other Irish people as well. But it’s not just the Irish people. It’s everyone has been so, so helpful. How can I help? What can I do? How can I spread the message? Who do you need to meet with? Who do you need to talk to while you’re in the U.S.

Aoife O’Brien [00:06:24]:

so, generally speaking, I feel like I’ve had much more access to senior leaders here, and people have been so open to meeting, which I think is a little bit different to my experience in Ireland and Europe generally. So I thought that was kind of an interesting kind of cultural difference between the two places. The other thing that I wanted to share is that story about the car. The way my brain works. I make these connections all the time, and I was thinking, this can be anything. It doesn’t have to be a car. And people feel like this all the time, and they let those things hold them back. Oh, the credit card didn’t work.

Aoife O’Brien [00:07:00]:

Oh, well, then it’s not meant to be, and I’m just going to turn around and I’m going to do something else or I’m going to set up something on Zoom instead. We hold ourselves back in this way and I do this as well. I could have let that be the excuse. And I kind of, like I say every fiber of my being wanted that to be the excuse for why I didn’t have to drive on the wrong side of the road. So think about what that means for you. Is there something that’s getting in the way even with every fiber of your being? Like, this is not what I’m supposed to be doing. I’m too nervous. It could be a job, it could be a promotion, it could be a difficult conversation that you want to have, but what does that mean for you? And then what tools can you use? So how can you make things easier for yourself? Do you need to upgrade the car so you have access to maps on the screen rather than having to rely on your phone? What can really help you achieve what it is that you want to achieve? Or maybe you’re happy where you are.

Aoife O’Brien [00:07:51]:

Although if you’re listening to this podcast, I would imagine that in some capacity, you want to make some sort of change. I will leave that with you. For today’s podcast episode, I’m sure I’ll be sharing more about my us trip on social media, so if we’re not already connected, feel free to reach out to me there. I’m most active on LinkedIn, and as always, if you have any questions or comments, feel free to reach out to me on podcast@happieratwork ie. And I’ll be back again soon with another interview episode and no doubt with another solo episode as well.

Previous Post: « 306: Redesigning Workplace Culture Without the Contract with Matthew Cook

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