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Thank you all for being here! I am super happy to be able to come to Boulder to chat with you all today.
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First off, I would really love for us to all thank Spike and the other organizers and volunteers. Planning and organizing a conference is hard work.
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The Ruby community was the first technical community that I really felt a part of. In addition to loving the language, the people who form this community are just such an enjoyable group of people.
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These small regional conferences are so much fun, and I'm so glad that Spike is rebooting Rocky Mountain Ruby.
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Let's all meet people, chat with each other, share knowledge, and just have a lot of great fun together.
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Almost all of my slides have been generated by DALL-E. I decided to hop on this AI train and make the computers do all my work for me. I hope you're entertained by some of the interesting choices that AI made on some of the pictures, and hopefully you're also impressed by some of the really beautiful images it was able to generate as well.
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So back to the talk at hand: A Blueprint for Making Scary Choices. Let's first start with a bit of background. So I'm Davy; I've been part of the Ruby community since about 2008. I've spent the last decade in engineering management and leadership.
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I've been lucky enough to work for a number of successful startups, a few of which you may have heard of. Now I work as an adviser for startups, serving as a fractional VP of Engineering and a leadership coach. If you look at my life on paper, it seems like I've done very well for myself, and in many ways, that's true.
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I've been pretty successful in my career, I've worked at some very successful companies, traveled all over the world, and spoken at a lot of conferences. But despite all the success, it didn't make my life happy. Something was missing that kept me from feeling as happy as I wanted.
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I had focused on building a career, but I had always thought that I would build a family as well. So let's set the stage: It's the end of 2020, our favorite year. The world is shut down, we're gripped in a global pandemic, and no vaccines have appeared yet.
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In my life, another promising—or what I thought was promising—relationship had fallen apart. I was now single, turning 39 in six months, and for some reason, turning that corner and staring down the last year of my 30s made it feel obvious that I could no longer claim I'm in my mid-30s.
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That was a trigger point for me. I needed to decide how important having a child was for me and, if it was, I had to take matters into my own hands. We all know that a woman's fertility drops with age.
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I was worried that I had already waited too long. It became painfully obvious that I was not going to find that hypothetical partner to have a child with. Was I going to be okay with the reality of what my life was becoming? I had to make some big, scary decisions.
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This is not a talk about parenthood. I made an unusual and still pretty uncommon choice in my path of parenthood, but I'm not here to say this is the way to do it. Instead, this talk is about how to make scary choices.
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Many of us grapple with decisions of this caliber throughout our lives across a wide range of areas. There may be similarities to the questions we ask ourselves—whether it be professional decisions about our career, such as whether we're in the right field or if we want to continue on our current path, or whether we want to be bold and start our own company.
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It could also involve decisions about going back to school, furthering your education, or it could be personal, such as where you want to live or who you want to have as part of your life moving forward.
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Okay, maybe not all of the questions are the same, but there may be times when we have a scary choice in front of us and it feels overwhelming.
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We might feel paralyzed by this choice and perhaps even decide to ignore making a decision because we're not ready yet. Maybe there's something on the other side of that choice that we desperately want but just don’t know how to get there.
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Sometimes we allow ourselves to stay in a state of unhappiness for long periods because we're unsure about how to decide what path to take in life. There can be many reasons driving these choices. Maybe you're feeling something is missing in your life, or perhaps you want to build more happiness into your life.
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Maybe you crave adventure, seeking something to give you more energy and excitement, or perhaps you want to prove something to yourself or to others.
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Now, about three years after making my own scary choice, I am happier than I have ever been in my life, and my 14-month-old son brings me more joy than I ever could have dreamed. Reflecting on my own process for navigating my scary choice, I have identified a couple of key steps that were critical to my experience.
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I hope that by sharing them, it might resonate with others and help them with whatever choices they are facing in their own lives.
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I'll go over six steps on the path for making scary choices. Depending on your personal situation and the choice you're grappling with, some steps may resonate more or less with you. I'm not claiming these are the six steps to make in order; that's not my goal.
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I would also love to hear which steps resonate with you, so if you see me later in the hallways, feel free to talk to me about it.
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Here’s the crux of my talk: We are all faced with scary choices in our lives. What choice is right for us? The first step is identifying your grief.
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When you have a scary decision in front of you, it likely comes with other emotions tied to that choice as well. You might experience fear, anxiety, or nervousness. There could be yearning, hope, or excitement about what you want your life to become.
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There might even be some sadness or denial about something in your life that's forcing you to make this choice. For me, I always thought that someday I would find the right partner. Partnership was something I deeply wanted.
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I spent all of my 20s and 30s dating, trying to find that person. When relationship after relationship ended, I felt numerous emotions surrounding my worthiness. What could I do to be more successful in this aspect of my life?
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I wondered whether or not I would ever have a family or build the life I wanted. So when faced with the choice of having a child without a partner, I first needed to take a hard look at my expectations surrounding partnership.
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I had to deal with my grief of knowing that I would probably have to put that goal and that path on pause, perhaps permanently. To even rationalize the decision in front of me, I had to spend time grappling with all of those emotions that were surrounding the idea of not finding a partner.
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Dealing with feelings of sadness, inadequacy, and failure meant that while I was still caught in the middle of those strong emotions, I was not in a position to move forward on a successful path to build happiness in another way.
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Not all scary choices are rooted in grief. If that doesn’t resonate with you particularly, there might be aspects that fit your situation better. Maybe it’s more about anxiety or fear, or maybe it involves a sacrifice that you have to make or a hope that feels almost too much.
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Many of us face a very real fear of rejection or failure. Is that fear of failure creating a wall, preventing you from moving forward? Many scary choices also have a monetary component, as the fear of living without often accompanies sacrifices necessary to change your life.
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Other losses can include time, freedom, hobbies, community, friendships, and relationships. All of these might contain elements of grief or sacrifice within them. Facing those fears and feelings and understanding the sacrifices that might be necessary is a healthy step that will prepare you for whatever path you decide to take in the future.
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Another mistake people can make is believing that moving forward with a choice is going to magically resolve their grief. This is a common misconception. We've seen tropes around this, right? For example, getting married will fix your relationship problems, or moving locations will solve your core unhappiness.
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Unfortunately, it is not that easy. The consequence of not dealing with your grief could lead to paralysis or procrastination in making your choice, or in making meaningful progress toward your goal.
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For me, I can look back and see that ignoring the realities around not finding a partner kept me in stasis for a long time. It took time for me to start dealing with my grief and sadness surrounding my situation.
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It was only when I'd reached a point of acceptance—if we're being honest, around 75% acceptance—that I was able to move forward with the choices in my life.
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Identifying and beginning to deal with your emotions will help clear your head and your heart, setting you up to make better choices and better experience the joy that might be coming into your life.
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You may not need to completely resolve these underlying emotions, but being able to move the needle a bit is a good litmus test. If you've worked on step one, here are some results you might begin to see in your life.
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You may no longer feel as frozen in your decision-making, recognizing that your grief or other emotions are independent of your choice. You might feel emotionally prepared to move forward.
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Step two is to embrace nonlinear paths. Society teaches many stories about how life should unfold. These narratives usually follow a linear pattern and influence our ideas of success.
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For personal life, think about milestones: meet, date, marry, have kids. Partnership plays a critical role in the measure of personal value.
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There are strong societal norms regarding single motherhood or having children out of wedlock. This linear thinking also affects our careers: we're often told to climb the corporate ladder, to progress in title.
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Moving into management is seen as a sign of success and we’re coerced to think that working at big tech companies means that you've made it. Or if you're a founder of a startup, you must secure VC funding.
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These linear paths can restrict our thinking about the potential for our lives. They may make us feel that if we're not following a particular path, it means we're failing.
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But I'm here to say that our paths are not linear. We don't need to restrict ourselves to a rigid plan for our entire lives.
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Stepping outside of these predefined paths does not mean you have failed. If your goal is at the end of one of these paths, it doesn’t mean you must go down every step in order to reach it.
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You can get creative with your path to reach your destination. I remember a conversation I had with my best friend when I was about 34 or 35.
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After yet another relationship ended, I was expressing my fears of never finding a partner to start a family with. She very kindly mentioned that I didn't have to find a partner: I could choose to have children by myself.
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My initial response was that I really didn't want to have a child by myself; I wanted a partner. This reflects not only my grief, but also how deeply I was tied to that linear thought process.
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I was clinging to a societal narrative around partnership and children, which prevented me from seeing other successful paths for building a fulfilling life.
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Taking the time to look at our lives from a different perspective is a valuable exercise that we should all do regularly. We often follow paths blindly without considering if they're truly what we want or if the destination is aligned with our desires.
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Are there societal expectations preventing you from expanding your view of happiness?
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These statistics I found online indicate that just because something is uncommon doesn't mean it isn't possible. You might find that you are less alone on your journey than you thought.
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This step is about opening yourself up to possibilities and letting yourself dream. After doing the work to release my feelings of failure, I was given the time and space to rethink what I wanted my personal life to look like.
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Did I want children? Would having kids—even doing it alone—bring me happiness? Biological children have a time limit, so this was useful for me; it encouraged me to explore options outside of the standard path.
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In the end, I figured I would regret never trying to have a child, and that realization set me on my path.
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If you're applying this step, you might start identifying societal expectations around success or failure that limit you. You can also start giving yourself creative permission to imagine broader possibilities for your future.
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Step three is about committing to yourself. It’s easier to make big, scary choices when we have someone beside us. However, it’s vital to consider if you’re willing to make that same choice even if alone.
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Spending time to think about what it means to take on the entire load of a choice can help clarify whether you’re fully committed. Having a child is a lot of work, and many people say I'm brave for doing it solo.
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And they’re not wrong. It is a lot of work, but it wasn't as challenging as I feared at the start. I believe this was partly because I committed 1000% to the decision.
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I had nine months to prepare myself mentally for the challenges and knew what I was signing up for. I'm not alone—my family is very supportive, and I have a wonderful father and engaged grandfather.
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My sister, in particular, deserves a shout-out for watching my son while I attend this conference.
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Committing 100% to this decision helped validate the choice and made me more open to celebrating joy in my life.
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In situations like marriage or founding a startup, where your choice inherently involves another person, it's still wise to contemplate what it would be like if you needed to take on more responsibility than expected.
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While we hope for balanced contributions, they may not always work out that way. For example, marriage isn't always 50-50; sometimes, one partner must carry more of the load.
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This step encourages you to consider the times when you may be completely alone while handling a significant task. Do you find you have the same commitment and understanding of the potential load? By contemplating this, you'll be better prepared for the natural ebbs and flows of life.
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Unexpected situations can arise—teammates might be sick, partners might be away, or circumstances could shift. Being prepared for those loads could set you up for more sustainability and awareness.
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This step may feel hard as it involves contemplating being completely alone, but taking the time to confirm that this is truly the choice you want to make can help ease your thoughts about the decision in the long run.
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Step four is about focusing on reciprocity. When you have many choices, you might worry about whether you're making the right one. How can you feel more confident that the path you choose will lead to personal satisfaction and happiness?
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One method is determining what provides you with energy, love, and inspiration, and focusing on spending more of your time and energy on those things. Love the things that love you back. Invest in what commits to you.
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This applies not just to love and friendship, but also to work, hobbies, and where you live. Early in my life, I committed myself to relationships that didn’t provide me the same level of commitment back.
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I thought if I gave all of myself, it would encourage someone else to reciprocate. I did the same in the corporate world, dedicating everything to companies that wouldn't acknowledge my efforts.
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However, experiencing reciprocal love from my son shifted my happiness and mental health positively. Even though my daily life became more challenging, I found myself happier overall.
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It's tough to fill everyone else's cup while your own remains empty. Now, my capacity to balance my energy needs for less reciprocal relationships has grown tremendously.
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Having a larger source of incoming love and energy makes a difference. However, each situation can vary due to late-stage capitalism. True reciprocity from employers may be asking too much.
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Reciprocity doesn’t always have to come directly from your employer. You might find satisfaction in making a difference, working in a field that interests you, or learning new things.
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Basic respect, advancement, continued learning, and responsibility should exist in an ideal working environment. We should be pushing for that as employees. Yet, there are circumstances beyond our control that make that difficult.
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If your personal choice does not involve reciprocity, evaluate your internal battery. Do you have the energy to take on a new endeavor? If not, what changes can you make to fill that battery?
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Will this choice create new positive energy in your life? It can be a personal experience—some people gain energy from hobbies, while others are influenced more by their environment.
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Human partnerships certainly play a significant role in our happiness. To make informed choices, validate whether they add energy or drain it. By neglecting this aspect of decision-making, we risk decreasing long-term satisfaction.
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Incorporating this step will enhance your awareness of your internal battery, channeling your focus toward creating positive energy while fostering confidence in your decisions.
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Step five involves uncovering hidden benefits. When faced with a scary choice, it can be paralyzing to focus solely on the challenges tied to that choice.
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I had to reconcile dealing with significant medical events and all that comes with raising a child. However, once I pushed past that initial wave of fear and uncertainty, I started to discover the various benefits of my choices.
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Some benefits were practical: having sole legal authority, not stressing about custody issues, and eliminating major stresses related to relational dynamics.
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Furthermore, I had unexpected perks: I've developed amazing sleeping capabilities due to necessity and found it easier to obtain a passport for my son as a single parent.
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Others remarked on my child's patience—I believe it's because I wasn't always available to respond immediately, leading him to develop resilience.
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When I finally released my attachment to dating, I recognized just how much negative energy it had drained from my life.
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I'm not here to tell you that you'll find enough benefits to outweigh the challenges of any choice—there will always be work involved.
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Looking for hidden benefits will help cultivate a more positive mental state. By mentally cataloging those benefits over time, even minor benefits can compile into significant positives.
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Recognizing these positives as they arise can help counterbalance any negatives you face with your choice. Understand whether those benefits align with creating meaningful impact in your life.
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This process shouldn't minimize the challenges involved; it aims to encourage you to see beyond the struggles.
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Finding the silver linings in any given experience can become a valuable coping mechanism.
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Instead of focusing on what you’re missing out on, try instead to appreciate what you have. Build your collection of joyful moments as a counterweight to life's difficulties.
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You have the power to build your own happiness, an ongoing effort—discovering those hidden benefits over time will help you maintain a positive attitude.
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Finally, step six is about taking that leap. At this point, you've spent considerable time evaluating your frightening choice. You've dealt with potential grief, allowed yourself to open up to alternative paths, and are ready to accept the risks of going it alone.
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You’ve also dedicated effort to identifying hidden benefits along the way, preparing you to leap. For some choices, this might not be as clear-cut as seeing two pink lines, but you begin to realize you've crossed the line from potential to actual.
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At this moment, you might feel calm and confident about your decision. Alternatively, you could experience anxiety, negativity, stress, and all those emotions that can derail your happiness.
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Constant exposure to stress can have physical effects on your wellbeing. If you tend to overthink situations, consider learning the art of surrender—to let things unfold naturally.
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Having gone through the previous steps equips you for success in your decision-making process. Now is the time for that preparation to pay off.
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The journey of starting a family through a fertility clinic can feel like you're performing magic tricks with several hoops to jump through. Managing timelines, appointments, and procedures isn't always easy; you may face delays due to circumstances outside of your control.
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And even when everything goes perfectly, there's no guarantee of success. I spent a year navigating this process, honing the art of surrender.
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Taking it step by step, I focused on each thing that needed doing, embracing setbacks gracefully while being attentive to my needs.
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Life is a journey, a climb towards a more hopeful and enjoyable existence. We can focus on the immediate steps and trust our preparations, making us more successful in that journey.
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To recap: by navigating through these steps, creating your desired path, and executing that plan, you can be amazed and proud of your accomplishments.
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We’ve made it to the end of my talk. I want to highlight that this was inspired by my personal experience, rather than any studies or science.
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I am looking forward to Dustin’s talk on happiness to hear what research says about building a happy life. My hope is that this talk sparks new thoughts for you regarding life choices.
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Thank you for your presence here. Keep your heart and mind open as you navigate through the rest of this conference and everything to come.
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