In 2017 when Dave Barry and I were making the “Dream Out Loud” documentary, we met a wonderful human named Aaron Govern. We initially talked to him because he was a big U2 fan, but when we finally met him in Vancouver, we knew he was so much more than that. I still think back fondly of walking through the city, stopping for tea at a café, and having one of those great conversations that are all too rare these days. He was English, so of course he was very particular about his tea, and I hoped he wouldn’t judge me for choosing a green variety. He didn’t. He was one of those people who just seemed to get it. And by it, I mean life in general. Over the course of that year, he became somewhat of a trusted advisor at times. And one idea he made clear, and one Dave and I still reference often, is a simple thought: If you don’t ask, you don’t get. It’s an obvious sentiment, but one that seems to be overlooked. If you want something, ask for it. Otherwise, how are people supposed to know? This comes into play so often in business. Someone has been working hard and wants a raise but doesn’t ask for it. Another is hoping to get promoted to a position that has recently become available but doesn’t tell anyone she’s interested. A new company wants a big client but doesn’t reach out because they don’t think they can get it yet. A podcaster wants big name guests but assumes his show is too small to get a yes so he never tries. Whether they don’t want to ruffle feathers, are afraid of rejection, or worry that if they ask for something and it isn’t well received, they’ll lose what they already have and end up worse off than before, there are many reasons why people talk themselves out of going after what they want. But if you don’t ask, you don’t get. I remember in 2004, my boss at the time got annoyed because I couldn’t read his mind. He actually said that. “The girl before you could read my mind. I need you to do that.” Umm. Okay. I can do a lot of things, but unfortunately that’s not one of them. He probably shouldn’t have let her go if that’s what was going on. But he did what so many people do. Instead of communicating and being direct, he expected things to happen on their own. Like he could think it and it would somehow come to fruition. Rarely does that mindset pay off. It’s usually fear-driven, or that sneaky imposter syndrome creeping in telling them they can’t get or don’t deserve what they want. So how do you build up the courage to ask for it? Keeping in line with my usual advice, let’s take the emotion out of it and think about the situation logically. First, what happens if you don’t ask? You probably won’t get it. So by not asking, you’re actually taking the bigger risk because that means you might not move forward, might not get that thing or experience that’s going to make your life better, or who knows what else. Then, realistically, what’s the worst that can happen if you ask? They say no. Okay, so you can accept that and move on, or in some cases figure out a better approach to ask again. Maybe your feelings will get hurt, or you’ll be disappointed, but isn’t that better than being constantly frustrated? Maybe that no will show you that it’s not the right job, client, or project for you after all, because the right one would align with your goals. In any case, if it’s a definitive no, that gives you information you need to move on, change direction, or set a new goal. In my opinion, working towards something new is always way better than wondering what if. Through that lens, hopefully it’s a little less scary already. If you ask and don’t get, then you have more information to help you decide what to do next. Even if it’s not what you initially wanted, maybe your new direction will be better. Trust in timing. Everything works out when it’s supposed to. It might not always feel like it will at the time, but one closed door might be leading you towards a better open one. Yes, I am still and will always be an eternal optimist. How do you get the confidence to ask? Nerves are normal. Doubts are normal. Hesitation is normal. But you have to push yourself through that. Preparedness is the biggest solution. Before you ask, you’ve done your research. You know what you want and why. You know why it’s the right thing for you, and hopefully why it’s good for the person you’re asking, too. You’ll go into the conversation armed with what you need. If it’s a job interview, you know your accomplishments and why you’re a good candidate. Tell them why you connect with the company and what you can offer them so it’s not one-sided. If you’re asking for a promotion, let them know what you’ve accomplished in your current role, how you could improve the company in the new role, and why you’re the best fit. If you’re going after that big-name brand as a new client, be ready to explain your vision for them and what ...
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