Bet on You: How to Win With Risk

Angie Morgan: Great question, because the first two books... we really did want to focus on these fundamental leadership principles that we learned in the Marine Corps and help translate to the private sector. So professionals everywhere could really understand that leadership isn't about a job title: it's about action and behavior.

And in "Leading From the Front," we really wrote that book toward women, to help them, because most women don't go into the Marine Corps: it's a really significant minority. So, we wanted to expose this curriculum to them.

And "Spark" was our second book, and we wanted to really distill seven leadership principles that we think would be valuable for anyone, at any stage of their career, to develop.

When we came together to write "Bet on You," we wanted to take a different tack with our work. We wanted to really dig deep into one specific subject that we felt could benefit everyone if they just really understood risk taking – what it is, and how it can help them benefit in their life to help them achieve their aspirations.

What's interesting, as we spent a lot of time leadership coaching, we talked to the most successful, intelligent men and women around the globe... and even the most confident individual still struggles with taking risks, [around what's] most meaningful to them.

Whether it's a career transition, whether it's making decisions for themselves outside of their business... it's opening up that Etsy business to dabble – if you will – to sell your jewelry that you've been making, into an open market. Or even if it's getting a secondary income, like investing in a rental property.

Those are the types of risks that we want professionals to get more comfortable taking.

Rachel Salaman: One of the reasons we don't take risks is that we're often scared of what could go wrong. In fact, that's, I guess, almost the definition of risk. What's your advice for how to push through that fear, or even dissipate it?

Angie Morgan: We write in the book about the two what we call "f'n cousins" [that is, a play on two related F-words or expletives]: fear and failure. And they're not the same thing, but they sometimes hang out together. Like the fear of failure, and that fear is amazingly powerful, and [is] paralyzing us from pursuing our dreams.

I have a friend of mine: she was at one point an executive director of a non-profit here in the United States, and she had really wanted to go into the independent contractor mode so she could have a little bit more freedom, a little bit more flexibility, a little bit more opportunity for her to earn. And her fear of making that transition was pretty powerful.

She said she had an easier time imagining herself homeless on the streets of Chicago, if that dream didn't pan out, than doubling her salary in two years. And that, to me, is the fear that many of us have. We can catastrophize what failure looks like: we don't spend enough time thinking about the glories if things could go right.

And so, we should have a healthy fear. I don't think anybody is purely fearless. So, we should appreciate our fears, but we should give the opportunity for success equal playtime.

Rachel Salaman: Mmm! And near the beginning of your book, there's a discussion about confidence and experience and how the two things interconnect. Could you share some insight about that in the context of risk taking?

Angie Morgan: Yes. Absolutely. I think a lot of people want to do and pursue these dreams but they feel like they lack the experience. And, in the face of experience, they also don't feel like they have the confidence to do what it is that they want to do. And so they over-value the experience, which diminishes their confidence.

And so, it's kind of a "chicken and egg" question that we often ask professionals: does experience give you confidence, or does confidence give you experience?

Well, we can't always accelerate our experiences: we are one person, right? But we can always build our confidence, and we can acquire what we like to call "second-hand experiences."

So, if you don't have the experience, talk to somebody who is out there doing whatever it is that you want to do. That can give you confidence, and those two things can fuel each other.

Rachel Salaman: Could you share a story, perhaps, from your own experience, that illustrates this?

Angie Morgan: I think about various times in my career – like going into the Marine Corps. I, obviously, had no prior experience of going into the military, but my dad had been a marine and that gave me confidence to see that I could do it. And so I always sought mentors or champions or people who are doing the things that I want to do and just asked about their experience. I'm entirely curious about that.

Even in 2004, writing a book, I reached out to a few people who I'd known [had] written articles for magazines. I didn't really know any authors but I just tried to acquire as much insight as possible into what the journey would entail.

Same with going through being a parent and the process. I didn't obviously... the first time I had a child... I didn't have any experience with children. But I babysat, I talked to my mom friends, and gained the second-hand experience to give me confidence for those moments.

So, I think, for those listeners out there, there's somebody doing what it is that you want to be doing, so talk to them. They can help bolster your confidence to see the possibility of it being pursued.

Rachel Salaman: Yeah, and, in fact, in your book, you include a whole chapter about what you call "guides": the importance of having people to support us in our work and life, and guide us. Could you tell us about a guide who helped you take a risk you wouldn't otherwise have taken?

Angie Morgan: In our book, we write about how success can be easier achieved when we have guides in our life. And we have three types of guides.

We've got "champions" – the people who support us.

We have "big stagers" – those influencers that we can access through podcasts (through the work that you're doing!) and just people who are building communities of like-minded individuals that can help them bolster their confidence that they need to do whatever it is they want to do.

We also have "no-choosers" – people in our life who are just there. Our friends, our colleagues; maybe we haven't had a direct hand in picking [them] but they may support us, they may not.

And so we have to have a strategy for either embracing and engaging or managing these folks in our life. And I will say that, all throughout my career, I have been very active in reaching out to people and just getting their perspective and insight. I love hearing people's stories.

In the book, I write about one particular guide of mine: he's the former Secretary of the Navy, Richard Spencer. He was very successful prior to going back into the Department of Defense. He was very successful in business. I reach out to him all the time with what I perceived as stupid questions, but he perceived as a really great honor to help mentor and champion a young businesswoman in her career.

So, I think about the early stages of building my company: he was just very influential on helping me avoid the pitfalls and navigate the environment to help accelerate my success.

Rachel Salaman: At this point in your book, you offer some great advice for "making the ask" when you want to enlist the help of a guide, which is something that stops a lot of people, I think, reaching out in the way you've described. And you say that we should be "sincerely curious" about that person. So, could you flesh out that idea?

Angie Morgan: I think, when people seek out mentorship, they think about it as a really formal opportunity for both parties. Like, it's almost like a marriage proposal: "Will you mentor me?" And that's not a realistic way to perceive it.

My way of looking at it is that there's a lot of people out there who would love – love, love, love! – to share their advice with you. So go honor them by being curious about their life and their success. People love to share their stories!

So, maybe another way to look at it is going to someone and saying, "I'm really impressed by your success. Can you give me 20 minutes? Can you give me 30 minutes? Just to share with me your story and some of the key decisions and what you were thinking at the time." Indulge people like that: people want to share their success stories with you.

And if somebody says "no" – it's probably going to be one out of every 10-20 people who say no – just respect the fact that they're probably busy. But most people would be honored to tell you their story in an effort to pass off lessons learned.

Rachel Salaman: Your book is full of lots of really great personal stories and metaphors, and one of the most striking, I thought, was the metaphor of the kaleidoscope. Could you explain that idea?

Angie Morgan: We're trying to help folks reimagine where they can take risks.

I think, oftentimes, people think about it as a career proposition, but we want to "widen the lens," if you will, because that's not the only place where we need to be taking risks.

I think what the pandemic has taught us is that having multidimensional pursuits in life can help us feel more balanced, more fulfilled, more harmonious with our lives. So we're advocating a "kaleidoscope approach" to risk taking.

And by that it means... if you think about the kaleidoscope, what makes the kaleidoscope so unique is you look in and each chamber of it has perfectly balanced chips in it. It makes a beautiful picture.

So, when you think about your kaleidoscope, think about, certainly, your career – because that's probably where the decisions you make are going to help you earn, achieve, find fulfilment in your professional life – but there's also your life.

Think about your family. Maybe it's something for physical fitness; maybe it's something for mental health or wellness, that you can take risks in. That could look like carving out 30 minutes each morning and doing yoga or breathing exercises or doing some sort of physical fitness. Or 30 minutes spending more time with your friends.

There's also areas in our life like service. I know a lot of folks, during the pandemic, really dialed down their efforts to be with their community, just with all the restrictions. But we're part of cultures. What makes cultures unique is when we all commit to serving them. And so there might be areas of your life where that's very important, especially this time in your life.

The final way is for fun. I can't tell you how many people I connect with who just don't invest in their fun. And, by "investment," it's not necessarily a financial investment, it's a time investment. They don't do things purely for them and their own joy.

Rachel Salaman: If someone was thinking, "Okay, I'm going to use this metaphor of the kaleidoscope in my life and I'm going to start tomorrow," what would that look like for someone using this for the first time?

Angie Morgan: To start, like, put a simple diagram on your paper: so, like a four-quadrant chamber.

Look at your career, ask yourself, "Am I happy? What would make me more fulfilled?" And just start writing down what decisions you could be making to help you feel more satisfied in that endeavor.

Or in your life, ask yourself, "What outside is working?" Maybe, "What isn't working?" and, "What type of choices could I make in pursuit of something more fulfilling?"

Same with service, and the same with fun.

I think about the "risking for joy"... I'm a mom, I've got two kids. I spend a lot of my time meal prepping, carting kids around, doing things that they want to do: maybe not enough of the stuff that I want to do. "Risking for fun" for me is going to concerts or live music with my friends: the music that I want to go hear, not the ones that they want to go hear.

And so, just start plotting out areas and opportunities where you feel like your life would be enriched through risk taking.

And that's a really great opportunity right now: just to talk about what risk truly is. I think, again, we think about it as this big word, "Risk," versus "Reward," like it's a downside of choice. Risk is really just a decision that leads you into uncertainty.

And we take risks all the time. So, if we take risks all the time, why not take risks intentionally to add to the fulfillment of our lives?

Rachel Salaman: You talk about fun there, but success is also about hard work, and I really enjoyed the chapter called "Do the Work," which reminds us that success doesn't come without effort.

And, here, you offer practical tips on creating the time and headspace to make that effort, which includes saying "No" to some requests. And that often feels risky in itself, doesn't it? So, could you talk about that?

Angie Morgan: We want to advocate for folks. It's not just "dream it!" You actually have to do it. You have to do the work. And, if there are things that are really important for you to pursue, you have to find the time. I think most of us do feel that we're time starved: we don't have enough minutes in our day to pursue the tasks, the goals, the dreams that we want to. You have to make the time.

And the best way to make the time is to start saying "no" and I was reading an article in The Wall Street Journal about this – in actual fact, this morning – that "no" can give you… It's one of the best mental health tools we have!

It can create time and space for us to take care of ourselves; it can create time and space for us to take risks on ourselves. And we call it the "Gutsy No" in the book because it is a risk in itself: telling people, "No, I'm not going to do that" or, "No, I'm not going to pursue this activity" or, "No, I'm not going to volunteer on Saturday."

It feels a little selfish. Yet, at the same time, it's your life, and we have to have the sense of freedom to be self-directed: that's very important for our own sense of wellbeing and satisfaction. So, saying "No" can feel gutsy, but it could be the one thing that gives you the space to actually do the work.

And that was the other point: when you create the space to do the work, make sure that's the space where the work gets done! Don't multitask; don't do laundry and pay your bills and "Oh, yeah, I'm going to get my business license right now" at the same time. Focus on whatever it is you're trying to achieve. Honor yourself with effort and action.

Rachel Salaman: And a related idea to this, which comes up a fair bit in your book, is "working in the margin of our lives." What is "our margin" and what's your advice around that?

Angie Morgan: The margin is our white space: so, no different than a piece of lined paper. It's that space that we're not supposed to write in but it's that buffer area where we can actually go over, if we have to.

So, I like to think about "margin" as... if you feel as if you don't have two hours in any given day in the week, that might be an alert for you that you need some more margin in your life. Margin is your space.

So, for me, it's often in the morning. My margin is from five to seven in the morning: really before my kids are up and go to school. That's when I do my most important work; that's when I do the work that I feel connects most to the risk that I'm seeking to take because it's quiet. It's just me. There might be a dog in the background but it's not too distracting, but that's when I get to do the work.

Rachel Salaman: So, we should... part of our sitting down with a blank piece of paper is thinking, "Where is our margin?" and, "If we don't have one, how can we create a margin?"

Angie Morgan: So, if you're a young parent, sometimes, it's putting a Disney movie on for your child – or whatever fun movie you want to play – and using that as your margin. Something that is uniquely a time for you. And maybe it's negotiating with your spouse, "If you could take the kids Saturday morning, here, I can use this time to focus on this." Or maybe it's in the evening.

You know you best. You know when, maybe, there might be opportunity to carve some time out in your life. Maybe it's forgoing evening television shows with the family to find the time.

I've always been amazed that the busiest of people find the time to do what's most important for them. You've heard the adage too: "If you want something done, ask a busy person." They just figure out how to get it done. So, treat whatever risk that you're contemplating with that same level of priority, and work to find the time to get it done.

Rachel Salaman: Classic advice! And another piece of really solid, classic advice that comes through in your book is to just do things properly. I think you use the words "Don't half-ass it!"? Could you give some examples of when we should heed that advice particularly?

Angie Morgan: Well, think about if you know somebody... we all know these people who cram for a test and fail. And they say, "Oh, I guess I'm not meant to do this." Like, if you're studying for... If you want to become a realtor and you don't really prepare for the realtor's license test and you bomb it, you might say, "Hey! I guess that wasn't meant for me." It's like, well, no. It probably was meant for you but you half-assed it. You didn't give it the attention and commitment, and now you're saying it wasn't for you: you're drawing a very invalid conclusion.

So, before you determine whether or not something is going to be successful or not successful in your life, don't half-ass it: fully commit to it.

So, if you do want to start a side hustle or you want to be an influencer or you want to get your blog, really commit the time and the effort. Take it to what we call a "choice point" to see if this is really something that could be viable. Because, if it's not, then that's great: then you know. At least you tried it. It may not work out. But, if it is, you can move forward because you have a lot of data through your experimentation that gives you confidence to encourage [you] to move forward.

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Rachel Salaman: That brings us to the idea of planning now, because you have some great insight in your book about how to plan and how to use a plan: slightly different thing. For example, you talk about "reverse planning." What's that tip?

Angie Morgan: This is the classic Stephen Covey: "Begin with the end in mind."

It was a tactic that we often used in the Marine Corps. When you create a plan, start with the day that the actual event is going to be taken. And, what you discover when you start in that way, versus going forward, is that you might be low-balling your goal.

So, you start to realize, when you reverse plan, that the task that you're seeking to cover is not only more achievable than you thought, but you might have a little bit more "higher ambition" with it. And you can start to anticipate, too, things that you wouldn't otherwise anticipate with a forward plan. And so, planning is important.

We also talk in the book about the one-third-two-thirds rule, where planning is great but don't seek to perfect your plan. If you've only got a limited amount of time, spend one-third of it on planning, two-thirds of it on executing.

I went to business school, and I remember my professor saying that there's practically virtual vaults of business plans that are perfect in design and concept but nobody wanted to do the work. And that's where, again, the adage of, "You've got to do the work: don't half-ass it"... If this is something you really want to do, put the effort and intention and action into it to see what type of results you can achieve.

Rachel Salaman: And taking action is the bit that a lot of people find difficult: especially the first step on a plan. How does a sense of risk play into that first step, and what advice can you offer there?

Angie Morgan: Yes. So, my husband and I, actually, last year – 2021 – we bought a café in our hometown – Traverse City, Michigan, here. So, it's a café and bakery.

And we started by conceiving the idea that we wanted to own a business, and this was nine months before the purchase. And we put together Excel spreadsheets to assess the viability of the type of business that we wanted to make. We talked to friends; we talked to some of our colleagues; we talked to fellow business owners to talk about the viability.

So, when the opportunity came to buy this business (it was already established), it was really exciting because, not only had we done the work, but we were ready to take that first step. And we are not baristas; we are not, necessarily, bakers. But, because we had done the work, taking that first step gave us a lot of confidence in the arena.

And, every day is a learning game for us, especially for us here in northern Michigan: we're approaching our tourist season. We're excited for the onslaught of tourists to come and frequent our business!.

But, at the same time, it starts somewhere. And that first step is scary. But, if you've done the preparation for it – and this is why we advocate for a responsible risk, not reckless risk – risk done right isn't a leap into an endeavor. It's planning, it's preparation, it's getting the courage, and then it's, of course, taking action.

Rachel Salaman: Wow! That sounds like a wonderful business.

Feeling safe makes a massive difference to whether or not we take a risk, and you address this in the book with a discussion of finance, talent and judgment: three things we need for a strong safety net. So, thinking about finance first, what are your tips for creating financial safety?

Angie Morgan: For most people, they have the resources they need to take the risk that they want to take. Yet, sometimes, for a lot of people, they never feel like they have enough money.

So, first and foremost, making sure that you get infinitely familiar with your financial picture before you take a risk. And these are especially with the risk that could be investing in a short-term rental or getting a business license and starting that type of endeavor. Or maybe it's transitioning from one career to the next, knowing that it's going to be a cut in salary but a major increase in life balance.

So, just making sure that you understand your financial picture, but don't over-strength on thinking you need – this isn't a financial term! – "gobs of money" to be able to make those decisions. I think, sometimes, we have to feel more than enough secure in our finances to make these decisions. So, we've got some guidance in the book.

And then we also talk, too, about your talent. That is your safety net, really, if you think about it. It's not necessarily your retirement plan or your employer: what makes you secure in anything is the hard work and the talent that you bring to it.

So, for right now, in your job, it's not just that you have a job that makes you secure: it's how you approach and engage in that work. And we've been building our talent our whole life. That should give you the confidence.

I know I talked earlier about a friend of mine making a career transition to become an independent contractor. She had the talent for that opportunity, she had the financial security, but what she needed to realize was that her talent was going to catch her. Her talent was going to... if this didn't work out... "I could pivot into something else."

And, finally, our judgment. This is really our decision-making skills. We write a lot about reaching out to people and helping build our judgment through those second-hand experiences of other people. That was one of the most important things I learned in the Marine Corps... is that how to develop my judgment, just by learning from others. By reading, by researching, building my perspective so I could trust my gut when the time was to make those decisions.

So, your finances, your talent and your judgment: that's your safety net. That's what's going to help ensure that, when you take those risks, that, if anything negative were to follow, you'd have something to catch you that would allow you to build from there or bounce back.

Rachel Salaman: Yeah. I was really struck by an anecdote in the book about your father, who was a school principal. And he used to talk about two types of teachers: those with 20 years of experience and those with one year of experience, repeated 20 times. The difference being the ability to learn and develop.

So, I think that's key to this, isn't it? If you're developing your talent, your judgment, and even your ideas about finance, it's about learning all the time from your mistakes and from what you can observe.

Angie Morgan: Rachel, you said a word earlier that was really important to this piece. It's "curiosity." It's approaching every single day as a learning opportunity.

And, while we don't go deep into this in the book, we certainly do in the leadership work that we take on through Lead Star, is [to ask]: "What are you reading? What are you listening to? Who are you talking with? What questions are you asking the amazing men and women around you?"

You can learn from anyone. And just making sure that you're reaching out and hearing people's life stories. Again, that can help expand your perspective. So much so that, when it is time to take those risks or make those big decisions, you have so much judgment and perspective that you're not even aware of.

Rachel Salaman: So, if we do position ourselves well to take risks and we do take the leap, but then we feel like it's not working out, how do we know when the smart thing to do is to quit?

Angie Morgan: So, Courtney, in the book, writes a really wonderful, poignant phrase: "You quit when it sucks!"

If you make the decision and you take the risk and you're just not finding the joy and satisfaction, you don't have to stay on that path! You've got the experience: you can make a "graceless pivot" as we call it – "graceless pivot." [That is, knowingly not graceful.] I've done this plenty of times in my life.

Thinking about the things that Courtney and I did earlier on in the business: somebody had approached us about taking our workshops on a cruise ship. We thought it was kind of tongue-in-cheek funny because it was the leader-ship, if you get it. Very, very profound!

And we started selling these tickets to this cruise and our event and it just wasn't working. And so, we thought it was a really brilliant idea until, actually, it wasn't working. So, we stopped. And the people who purchased, we gave them the money back: "This was a really bad idea. Sorry, we brought you into it but, hey, it's just not going to be working out."

And you move on: you learn from it. It was a wonderful learning experience. Believe me, next time somebody approaches me with a cruise ship opportunity I'm going to think twice. And it was, again, awkward and clunky, but we learned and we grew from the experience.

I also think, too... I'm a runner. There's plenty of times that I've signed up for races and things just get busy: I don't have the time to train. Suddenly, training is more stressful than it should be. And I'm just like, "You know, this is just not the time to pursue this activity," and you back out. There's nothing wrong with that.

I don't think of it as "quitting" in any of these endeavors. I think about, "Well, this didn't work out; I learned something; I can grow from the experience."

We put so much pressure on ourselves around the word "failure." I don't think of things that don't work out as "fails." I think about things as wonderful experiences that I learned and grew from. And I think that's the "shiny penny" in me: the person who always sees the optimistic opportunity in everything.

But, to me, it's a better coping mechanism than a "beat yourself down." Yes, have a moment where you're like, "Uh! Maybe I'm slightly embarrassed about that... " but dust it off your shoulders and move on.

Rachel Salaman: In the book you also point out that it's important to step back and acknowledge wins as and when we do achieve them. So, why is this important, and what are some ways to do this?

Angie Morgan: When I talk to a lot of professionals about the concept of winning, they tend to see it in these epic "mountain top" moments, or when they're battling something and triumphing. And I think, in our society, we kind of celebrate those moments too. Like, that eagle soaring through the sky or that climber on top of that mountain with their arms spread open.

But winning happens all the time. We have to be present for it. And the reason it's so important is it fuels us, it gives us inspiration, it ignites our confidence, it makes us find satisfaction.

So, there are wins around us every single day. It could be... even if it's just finding that margin in your life and finishing an Excel spreadsheet that was going to be your P&L [profit and loss] for the business. That is a huge win.

You have to take the moment to pause, pat yourself on the back, and just stand there for a second. Winning could be having a cup of coffee in the morning by yourself, reading a book: that's a winning. And being able to say, yourself: "This is what winning feels like to me."

Being present for our wins is a great reminder that we have success in our life, and we can use that to fuel, again, our confidence, our inspiration, our day-to-day.

Rachel Salaman: Well, we've covered a lot of ground in this discussion. What do you think are the top take-aways?

Angie Morgan: I hope people leaving this start to reimagine risk in their life: that it's not this big, scary, pitted-against-reward activity, "risk versus reward." That they see risk as the path to reward. That they take some time to reflect upon their personal risk disposition, and they take some time to think about where they could be risking in life to find greater joy, fulfilment and satisfaction.

And take that first step. It doesn't have to be that leap. It can be just that first small step to pursuing whatever is on their heart and in their mind, and just taking it each day, forward.

Because that's really how success happens: it's in increments, it's not in those leaps. And it's possible and achievable for everybody.

Rachel Salaman: Angie Morgan, thanks so much for joining us today.

Angie Morgan: Thank you so much, Rachel.

Rachel Salaman: The name of Angie's book, again, is "Bet on You: How to Win With Risk" and it's co-written with Courtney Lynch. You can find out more about their leadership consulting firm, Lead Star, at leadstar.us.

I'll be back in a few weeks with another Expert Interview. Until then, goodbye.