Finding Alignment: The Journey from Corporate to Personal Fulfillment

When Saara Lampwalla left her corporate role to build something of her own, she entered a season defined by visibility, vulnerability, and the courage to be seen in a new light. In this episode, David and Saara explore what it means to align your inner values with how you show up in the world — and how that alignment shapes both your fulfillment and your freedom.Key TakeawaysVisibility is a double-edged sword — it can both empower and intimidate.Aligning inner values with outer expression builds authentic leadership.Transitioning from corporate to personal work takes courage and experimentation.Being seen and being perceived are not the same thing.Redefining success on your own terms leads to fulfillment.Chapters00:00 – Exploring Visibility and Authenticity01:56 – Transitioning from Corporate to Personal Paths05:04 – Balancing Public and Private Selves07:04 – Aligning Internal and External Values09:10 – Embracing Authenticity in Professional Spaces11:51 – Redefining Success on Personal Terms13:57 – The Power of Being Seen17:12 – Navigating Professional Growth19:39 – The Journey to Personal Fulfillment26:53 – The Courage to Be SeenCredits & LinksHost: David SherryGuest: Saara Lampwalla

I spoke with someone recently who was *really* stuck. I’ll call him Joe. Joe was not just stuck professionally, but with his relationship (on again off again) and with his work (not sure if he should change careers or Not just professionally.When some people get stuck.. they get really… really… stuck. They find that multiple areas of their life start to feel stagnant. They can’t choose where to live. They can’t decide if they should quit their job or leave a relationship. They seem to be caught oscillating between these decisions, never moving forward.The good news is that if you can start to make progress in one area, you can start to make progress in many. All it takes is a little momentum, and suddenly the damn will burst. If you aren’t feeling like you’re making progress, the good news is the worse it gets, the more likely that it will get painful enough to break the tension.Tension is what you feel when you get pulled forward and backward or left and right with no progress.The trick that’s being played on you is that you think it’s about deciding. Being so focused on a decision, such as “Should I quit my job or not?” Or “Should we break up or not?” Is actually the wrong focus. It’s not the decision that is the problem, it’s something deeper which is preventing you from trusting yourself and hearing yourself enough to make natural decisions that move your life forward without so much effort, thinking, overplaying, and pain.What we’re really talking about here is our energy, and whether or not it is flowing or whether or not it is trapped and stagnant. We stop our own energy from flowing, and that keeps us stuck.The trick to breaking the damn is to get your energy flowing again, and that involves trust. Trust is needed to move forward, because decisions we feel are important require us to take a leap into something unknown. No matter how much you want to predict your future, or how much you think you can even project the future, you can’t. Ultimately it takes a leap of faith to move forward.The good news is you can start small. You can domino small decisions into larger ones. What’s one thing that has been put off due to your inability to decide or take action? What’s one small thing you can clear from your backlog?A client of mine, a CEO of a $30M+ company, he realized that he was prone to letting his metaphorical “Desk” get messy. It was so messy with so many problems and decisions and moments of not saying how he truly felt that it was covered with so much it was hard to work.The trick was to start clearing his desk. One thing at a time until he finally started to get some space again. Then, in the future, it was about being proactive enough to clear things before they became a problem for him.Your energy unlocks when you let tiny decisions compound into bigger ones, and when you let your energy flow instead of stopping it by trying to predict and protect yourself from the unknown.

Join David Sherry in this episode of Founder Therapy as he discusses the crucial distinction between intuition and fear in decision-making. Learn how to recognize whether your decisions are driven by genuine intuition or by underlying fear, and discover strategies to navigate discomfort when stepping into unknown territories. David shares practical insights from his experience working with successful entrepreneurs, including a real-life example of a challenging executive hire decision. Watch now to gain clarity on making the right choices for personal and business growth.

One of our earliest photographers at Death to Stock was Patrick Chin. Patrick had built a business in the luxury hotel and fine dining space. This meant that Patrick had to fly around to take photos at beautiful beachside hotels, or snap images of Michelin star Chef’s beautiful creations…getting to taste the dishes afterwards. Poor Patrick.Patrick showed me that who you choose as your customers matters. And that if you’re going to choose someone to serve, choose someone great.I had another friend who was a photographer for new startup retail businesses. They had very little money, fast turnaround times, and often burned through the images quickly. This other friend was constantly struggling with business and was frustrated. Given that you can choose your customers, who are the best customers worth choosing?

One of the compliments I receive most often in my work is something along the lines of:“You ask such great questions.”This probably comes after I ask someone some questions that I’m curious about. You get better at asking questions when you begin seeing them as a tool to have better and more valuable conversations. Questions set the frame of the discussion, and so leading someone is often about questions rather than making statements. Questions can be used for a variety of different purposes. Today I wanted to outline 5-levels of value oriented by particular questions that people ask of me and ask themselves. If you want to create/expand value, ask questions higher up the ladder.The Value Ladder: 5-Levels of Questions for Leaders1. “What do I do?”When you are working in a new role you’ve never been in before, you get tripped up on the question “What do I do next?” When you don’t know what to do, you don’t act. And so you wait or search for someone or something that can tell you what to do. Most often, this is a way of procrastination. You can’t act until you clearly see a specific, short-term step and action you can take. What do I do is the lowest leverage and least valuable question to ask of yourself or others. But it is often the place we start.2. “How do I do it?”Many people take similar actions, but not all get the same results. Why? When you don’t understand the “why” behind how something works, you lack proper form. Form is “how” you do something. “How” is a question about form. How helps get you to feel/experience the action rather than intellectually understanding it. How is for practitioners seeking to learn how to apply something they’ve learned. How is for doers… in an organization, team, community, or political structure. “How” is, relatively low value. Often, to succeed with how, you sell something at lower price points and therefore must have a large audience.This is why “how” is the most prevalent form of content on Youtube, for example. “How” is also the easiest question to waste your time on. “How” is a great game of telephone. You read someone else’s “how” and translate it poorly to your own situation and then get frustrated by not getting the right results.3. “Who?”When you wake up to the limits of your own “doing” you begin to see the benefit of collaboration, hiring, delegation and managing and leading a team.Who is the first leadership question outside of self-leadership. Who is the shift from Founder-Doer to CEO-Manager, from actor to recruiter. Who marks the beginning of systems-level questions. Before you get to “who” you focus on your input into the system.When CEO’s come to me with struggles for their personal productivity, I often take them out of “how” questions and into “who” questions. I’m less interested in them and more in the teams and systems that support them.4. “Where should we go?”Systems need direction. “Where?” charts the course. “Where” is about the future, whereas the previous questions are more about the present. Where questions are about owning the responsibility of taking people into the unkown. If organizations don’t know where they are going, then everyone is working out of sync and unison. Where is one of the greatest possible filter questions because it completely changes the course of a company or team. Change the where, change everything. A where question for Kodak Cameras was: “Double down on Film, or Enter the Digital Camera Space?” A question for NASA is: “Moon or Mars next?” As you can see, asking “Where” is risky. This is why “Where” is the CEO's question. With “Where?” there are consequences, or regret. Aligns a system to a destination, puts resources on the line, and creates definitive direction.The trick of understanding organizations, communities, and political parties is that they crave direction. They ask, “Where are we going…together?”5. “What does it mean?”The final level of value is in meaning questions. When you’re so distracted by the doing of things, you try to ignore lives deeper questions around meaning or meaninglessness.The good news is that we are meaning-making machines. Meaning making is about how we interpret the events around us, and how we contextualize every other question listed above. The highest levels are about context.In meaning questions, you are playing with the container, not the contained. You start playing with the rules, the stadium, the field, not the game or players on the field. You start working on the museum rather than the art sitting in it. Meaning is about creating context, and context is how we come to understand ourselves and the world. Context creators, meaning makers are storytellers. This is why Steve Jobs didn’t say, “The most powerful person in the world is the doer, the creator.” He said,“The most powerful person in the world is the storyteller.”Stories write and create invisible scripts and lines of action. Leaders working at this deeper level are playing a more invisible game of power and creation that comes from generating systems without being stuck inside of them. These leaders allow, encourage, and generate the success of others without being seen or heard.“A leader is best when people barely know he exists, when his work is done, his aim fulfilled, they will say: we did it ourselves.” Lao TzuThese inventors challenge our current frame of reality. They see outside of the container. If Tom’s Shoes invents “Buy one pair of shoes, donate one pair of shoes” as a way of making our consumption, and then other companies follow suit, eventually forgetting the original creator of such an idea or protocol. Tom created new meaning.Climb the Ladder of Your Own QuestionsThe next time you feel stuck, I want to offer a little challenge:Don’t immediately look for a better answer.Ask:Am I even asking the right question?What level of the ladder am I playing on right now?What happens if I climb one rung higher?

“What are the levers that I can pull that are going to help me create more value?”Say you want to charge more, be more known, get better testimonials, get more respect from others… the simplest pathway is to expand the value you create for others.Value creation is often thought of as a skillset, but what if how you think about value shifts your potential for creating more of it? Here are some ways I think about creating more value…1. Make Their Vision BiggerWhen I meet with a client for the first time, my gut reaction is often to ask, “Are they thinking too small?”They might say they want to launch in one market, and I’ll ask, “What would it look like to launch in five markets this year?”Thinking bigger increases excitement for projects. You want to increase excitement only to the point of slight impossibility so that the discomfort isn’t too strong. We’re not here to merely make happen what is expected, we’re here to help make the unexpected occur. In teams, 2+2 = 4, or 6 or beyond. That is the beauty of working with others.Each person adds new capability, new insight, or possibility. Even if you’re an employee, thinking this way can expand the value you bring to whoever you work with. You’re not always going to follow through on every huge idea you propose, but at least you’re expanding the potential reality you can help create.You want to move beyond assumed value or possibility for how well things can go, and contribute your part to create a greater whole. 2. Multiply Value by OverdeliveringPeople say, “Charge what you’re worth.” I say: “Overdeliver on the project significantly beyond what you charge.”Whenever possible, you want to add to the “multiple” of value someone receives when working with you. In an ideal world, customers should get 2x-5x+ of the value that they’ve paid. Skewing value in the favor of your customer creates an abundance loop. Ask yourself, “How can I overdeliver on this project?” It might be sending your clients extra resources or even something as simple as remembering birthdays and sending a quick message. Some examples…Send monthly progress recaps, highlight new opportunities that weren’t previously seen. Offer bonus calls to brainstorm and problem-solve.Connect your customer to people you know who can also help them. Share mini “toolkits” of templates, how-to guides, etc. with clients.3. Stay Focused on Transformative ChangeGreat products create transformative change. They transcend beyond what someone “wants” and explore and expand into what someone needs, dreams of, and has never considered before. If you do only what your customer wants you to do, you are creating products based on a view of the world with limited knowledge. The benefit of expertise and mastery is your ability to see significantly more than others in a particular area or subject. It’s hard to say “no” to someone. Doing so, though, create the ability to guide and lead someone through a process that they might not have been able to previously imagine or understand. When you hire a travel agent, you don’t want to just tell them what to do and have them book it for you. You want them to think of what you never thought of, make decisions you might not immediately understand, and recommend what you would never find yourself. Steve Jobs knew, simply, that people wanted to buy the latest CD player, and yet he said no so that he could create something much greater with his iPod.Creating more value isn’t about just having the skills to do so – it’s often understanding what’s possible, having and building confidence to deliver, and being willing to explore unknown territories that may feel uncomfortable at first but help you expand what’s possible for yourself and others.What mindset helps you stay focused on creating more value for others? Or what have you done as a habit that has helped you?

Creating StreaksStreaks have always been helpful to me, building a chain of habits that help you see your own progress. For entrepreneurs, they are especially important because it’s so easy to feel like you aren’t making progress. Many entrepreneurs tell me, “I get to the end of the day and it feels like the scoreboard is reset to zero.” Yikes.Jerry Seinfeld was always a big proponent of this idea, saying that the best thing you can do as a comedian is “Write jokes, every day” and “don’t break the chain!” He uses a calendar and writes a big “X” on the day when he would write jokes.Right now, I’m following “The Way” meditation app, and I’m about 80/100 or so Meditation sessions in. It’s nice when apps track your streak for you, however, I have also been using Excel spreadsheets a lot lately. Simple TrackingI used to be a heavy user of different tech and tools like Notion or Evernote and kept up with my work with more intense systems. Today, I mostly use Excel, my Apple notes, and then one-off Google docs for simple reviews. ChatGPT, of course, is up regularly and is sort of a booster pack to whatever I’m already doing. It’s been fun to track what I’m reading, the comments I’m getting, and what my workouts are for the day. I feel good tracking because I’m able to better recollect progress. I think that when you have ADHD, you do more than most people and feel like you’ve done less. Mostly, what’s probably missing is a sense of completeness of tasks. I notice that even on weekends that there are days when I make a to-do list, I simply feel better and feel more productive. Tracking my WritingWhat metrics do you track?What we choose to track really matters. You probably don’t spend nearly enough time thinking about this. If we track outcomes and external validation, we’re going to be stuck in a terribly difficult loop that we can never get out of. Tracking our effort as an input helps separate who we are from what we do, or maybe it combines it, in a way that makes us feel better when we’re taking action. This simple point; knowing what to track, and then tracking it, while avoiding the trap of tracking things that simply don’t matter – is surprisingly difficult. Social media tracks things on your behalf, they are a default metric that you are forced to care about. On social media, I believe “comments” are the best thing to track. Or you could say you track positive interactions with your community. I think that’s a fairly decent metric as it involves connection. Most other metrics are totally pointless. Even then, I can’t really *create* comments and not all comments are the same. Knowing what to track, and why it matters to you will take your life in completely different directions. Mr. Beast has optimized his entire life around a game that I think is somewhat silly: Youtube’s algorithm. He’s the best person in the world at optimizing for Youtube’s algorithm. Because of that, his choice of what to create is limited by that filter. I don’t look up to someone like Mr. Beast because it’s not something I care about at all. And that’s OK. I’m mostly talking about knowing that for yourself rather than feeling the allure of someone else’s game that actually means nothing to you. If you told me I could have 1Million views on a video tomorrow, but it had to be in the style of Mr. Beast, I wouldn’t do it. That’s obvious because I’m not doing it.The Good LifeTracking what matters to me let’s me stack my good days, good sessions, and good moments together. If you can design your life in such a way that you have many good or even great things happen every single day, that, to me, makes a great life. Feeling successful doesn’t have that strong of a connection to achievement. That’s another false metric we link and track. Typically, people feel successful when they are in pursuit of their dream. You don’t even have to succeed at it. You simply have to succeed in doing the things that you desire and dream to do. Athletes lose most games they play, that’s the essence of the sport. Maybe they will dominate for a while. It doesn’t really matter, they are chasing their own dream.My friend Kristi said something profound that was a great visual and quote,“We watch athletes and sports stars on TV because they are chasing their dreams. Instead of watching them live theirs, what if you lived yours?”Tracking actions related to your dreams is a great start, and you don’t need any fancy software. What streak are you starting or continuing today?Making this your ownSo, how do you apply this in your life?Pick 1–3 Key Metrics – Make sure these matter to you (e.g., meditation streak, pages written, workouts, interactions with your community).Use Any System That Works – Calendar, spreadsheet, or a simple notebook. Apps are great if they help you—but if it’s too complicated, don’t force it.Celebrate Your Streaks – Even a three-day streak is a success. Don’t underestimate the power of small wins.Avoid Comparisons – Don’t let other people’s metrics distract you. Focus on what keeps you fulfilled.

Time to “Buckle Down”I was talking to a client today, and we discussed the opportunity to resolve a major problem in their business that needed attention. The tone of the team and the discussion centered around the idea that now was the time for them to “Buckle down, get to work, roll up their sleeves, and make sacrifices for a little while to resolve the issue.”I questioned the idea that this time was any different than before, and I wondered (with them) about what they were really getting at in this moment. Is it that the team isn’t really working hard? Is it that the team isn’t working on the right things?What makes this time truly different than other times?What does self-sacrifice mean to you? What is your connection between self-sacrifice and success? Are they linked?I cautioned that self-sacrifice, a common trait among entrepreneurs, works to drive towards goals and is also unsustainable. The Drawbacks of Self-SacrificeWhen the setup for success is based on self-sacrifice…You are thinking short term: Your focus is only on immediate fires, and being the hero to save the latest one. You lose perspective for your larger vision in pursuit of short-term fixes. You lose sense of who you are and what you want: Self-sacrifice is based on “giving up” part of you for a cause. Do the causes you truly care about mean giving up yourself in the process? There will always be more things to sacrifice for: There is always a new issue, fire, or problem that needs to be handled, and the more used to using the fire alarm as an incentive to act, the more you begin to rely on it. Self-sacrifice is Unsustainable: It drains your reserves, leaving you to lack the resources for the long game. It only works for so long, leads to burnout or team problems.Crossing the Finish LineIn Olympic Skiing, it’s not just the person who finishes first who wins the race. It’s the person who didn’t get injured and was able to compete that day. You can’t win if you can’t compete tomorrow. Winners win sustainably over the long haul. Ownership, Choice, FreedomYou want to watch for the tone and energy of self-sacrifice on your teams. Other people will try and impose their need for it as fuel. If a team operates under the idea of self-sacrifice, it will create disconnection and isolation, preventing the development of a collaborative team environment characterized by connection, support, and even enjoyment while solving significant issues.You might think back to a time when you achieved something without self-sacrifice. If you can think of one, then maybe these things are not as linked as they initially appear. Desire, excitement, team-work, responsibility, vision… these are all great motivators. When you pursue things from these motivations, you are less likely to put yourself in the frame of mind that this is “hard” and requires you to give up parts of yourself to get it.Yes, there is work to be done. Also, it will take the long-term sustainable path of consistently showing up to work which will help resolve it, not short-term heroism. 

When I talk with clients, there’s always a dance – where is this conversation most exciting for them? Where is my excitement? What is productive? Where are we going?I notice the subtle ways in which my body opens up, or closes down, how certain topics create constriction in me or the other person. This type of awareness can itself be draining; rather than being fully relaxed in a conversation, I’m paying attention to too many different cues.For a long time I was really exhausted by meetings. It wasn’t until I noticed that I had this dual process going on: I was speaking, while also trying to pay attention to how I was being seen while I was speaking.This is surprisingly common – you notice that you’re both trying to pay attention while also worrying about how you’re seen. This is especially tough when you’re leading meetings and you feel like it’s getting out of your control. Now I can get into a pure awareness type quality where when I speak with others I simply direct my focus on them. There’s no more dual track, and when I speak I speak with my own energy going towards them. Dropping the need to “see” how I’m being seen. How do you do that? No Agenda MindsetYears ago, I had a (temporary) podcast that was called No Agenda. The name came from a Tao like idea of having no view about where things need or should go. When you have less of an agenda for others, things can unfold naturally. Having an agenda for someone else, we feel them trying to push us in a particular direction, and most times when we feel pushed we push back and it creates resistance. No Agenda as a mindset is about creating less resistance in conversations. When you drop your agenda (needing to create an impact) you also drop the need to track your impact as much. Of course we all have some type of intention or agenda, but the more you’re in your own being as you speak, without it needing to make an impact, the less you care about the way you’re received.Often the better you feel as you speak, the less you are paying attention to the crowd. See what it’s like to drop the agenda you have with others when speaking and feel the weight get lifted. What lights you up to talk about?One of my favorite questions is, “What is something you love to talk about but people rarely ask you about?”It’s fun for you because everyone has areas and topics that you know way more than you other people. Even if that topic is how to fix an old Mustang or deep knowledge of a board game.My first business partner and I worked together simply because I had enthusiasm that I think they could feel, and this turned into their enthusiasm, which allowed us both to partner together profitably. Creating mutual excitement is underrated as way to move partnership forward. What Coaching IsOn a deeper level, conversations are how we learn about who we are and learn about who others are. If you want to learn more about yourself, have more new types of conversations. This is part of what coaching is, helping people have new conversations with themselves and others.Another hint here is that conversations are more fun when you feel like you’re entering new territory. As part of this, you want to ask questions that people have never been asked before. Some of the best questions sort of stop people’s brains from processing on autopilot. You can ask new questions or ask questions in weird ways. You can feel people trying to give you their stock answer and it’s fun to see if you can help them get into new territory. Some people won’t be open to that and will shut you down or simply pretend they don’t hear you.Sometimes, when I talk with people about certain topics that they are unable to allow themselves to access (due to vulnerability, taboo, belief, etc) I ask them a question ,and they simply just act like they didn’t even hear what I said and keep talking. Here, I don’t push, I take it as a sign that they don’t want to talk about or are not ready to talk about it.Conversations are much easier when someone is engaged, excited, and almost can’t help themselves from telling you more. This only works when you’re spontaneousPeople are incredible at picking up authenticity, so you can only do this type of work if you have genuine curiosity. Even a question like I listed above becomes stale when used as a stand-in question. It needs to be alive in you to be alive in the other person and needs to happen spontaneously. Where do you get the most joy when having conversations? Where are you stuck or held back?

People launch businesses for wildly different reasons…Escape the corporate lifeMake a lot of moneyCreate a meaningful product or serviceHave flexibility in daily lifeBuild relationships and be seenThey’re chasing something that they believe that business, as a vehicle, can give them.But once you're in the midst of creating the business or doing the new type of work, you realize it might not always give you what you are looking for.For one thing, you don’t achieve freedom once and check it off the list. Purpose isn’t something you discover and then never have to think about again. Money comes and goes (often). Running a business isn’t a static experience—it’s a constantly shifting process. And the sooner we recognize that, the sooner we can start to see our business for what it actually is: something that evolves alongside of us, and even changes depending on the day, depending on how we feel, or how we’re choosing to show up.I remember learning a tough lesson about freedom and business.I remember walking down the street on a beautiful sunny Tuesday, heading to get some work done (this was 2018), and then realizing I was feeling completely anxious about the day ahead. On paper, I was free. I didn’t have a boss, a fixed schedule, and no one telling me what to do. But internally, I wasn’t free. I was carrying stress, worry, and pressure with me everywhere I went. I couldn’t enjoy the sunshine, and I was feeling a bit terrible walking into the coffee shop to check my email. I learned that external freedom—no boss, no set hours—doesn’t mean much if you’re not also free inside. I hadn’t considered that I would need to learn internal freedom as much as I would learn about creating external freedom.That’s a tough lesson to learn, and it made me question what I was really after at work in the first place. I had forgotten where I started, or maybe I had evolved and found myself seeking something different. What Do You Want from Your Work?At different phases, our work can provide us with different things. I often find that businesses give you exactly what you need when you need it. Sometimes, I see business owners who really need stability in their business because their home life is having a huge crisis, and it somehow supports them through. Othertimes, a business owner is undecided, and the business forces them one way or another. What we want and need evolves, and maybe now for you, it’s more about your creativity, your relationships or finding financial security for the first time.The best thing you can do is check back in with your current set of needs. What do you want, right now?If you look for it, you’ll find it.Instead of waiting for some distant milestone—freedom, success, purpose—how can you start connecting to those things today?It exists there, however small, and if you recognize where it exists, you can put effort into expanding that part of your work and life to have more of it.Right now, I’m really focused on my own creativity and experiencing my own creativity. My work is giving me these beautiful moments of feeling fully creative and fully alive through my work and writing and video creation. I’m seeking this out, I’m recognizing when it’s there and when it’s not. I’m allowing myself to give myself more of what I want. You’d be surprised at how much of success (in any area) is about allowing and embracing it instead of pushing it away. Can you allow yourself to have the freedom, purpose, or income from your business that you’ve been seeking?What if you already have the freedom or meaning you’re after? Look for it in the small ways, or recognize what your work is telling you about what you’re truly after – like a reflection in the mirror….Your business isn’t going to give you freedom or purpose—you get to discover it for yourself through your business as the vehicle for your growth and exploration.I wish I had been more grateful to have noticed my insecurity and stress in the moment, seeing how my work was telling me what I needed to hear and showing me what I needed to see. It sent me on a path of finding internal freedom after I found it externally. I’m on another type of pathway now – one related to creativity, and I believe that I’m more aware of its gift to me now.