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Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM @Slack)
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Kenneth Berger coaches startup leaders on how to prevent burnout, advocate for their desired lifestyle, and make a meaningful impact on the world. He’s spent more than 20 years in the tech industry, is a former founder backed by top investors, and was the first product manager at Slack. Kenneth’s core mission is to help startup leaders change the world by learning to ask for what they want, living with integrity, and building genuine relationships even with the people they find most challenging. Currently he is writing a book, Ask for What You Want, in which he aims to share his actionable strategies for creating change in the world. In our conversation, we explore: • Why asking for what you want is so impactful • Three steps to effectively ask for what you want • Challenges that arise when people struggle to ask for what they want • Why hearing “no” is a normal part of the process • The “dream behind the complaint” technique for uncovering desires • Kenneth’s experience of being fired three times from Slack • How embracing fear and discomfort is key to getting what you want • Why discipline is overrated — Brought to you by: • Sidebar—Accelerate your career by surrounding yourself with extraordinary peers: https://www.sidebar.com/lenny • Webflow—The web experience platform: https://webflow.com • Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Find the transcript and references at: https://www.lennysnewsletter.com/p/ask-for-what-you-want-kenneth-berger Where to find Kenneth Berger: • X: https://twitter.com/kberger • Threads: https://www.threads.net/@kberger • LinkedIn: https://www.linkedin.com/in/kberger/ • Website: https://kberger.com/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Kenneth’s background (04:31) The importance of asking for what you want (06:36) Challenges that arise when people struggle to ask for what they want (08:09) A personal example of failing to ask for what you want (09:17) Signs this is a skill you need to work on (10:49) How to get better at knowing what you want (15:28) Why hearing “no” is a normal part of the process (17:29) Getting a “yes” vs. a “hell yes” (19:20) Step 1: Articulate what you want (24:07) Doing an integrity check (26:56) Step 2: Ask for what you want intentionally (30:45) Understanding your influence (34:48) Using complaints as inspiration (36:24) Internal family systems (38:00) Giving feedback (41:24) Step 3: Accept the response (45:22) Kenneth’s experience of being fired three times from Slack (57:30) Advice on being the first PM at a company or startup (01:04:58) Contrarian corner: anti-discipline (01:05:52) Lightning round Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.
Segments Timeline
The Journey from PM to Executive Coach
Kenneth Berger shares his transition from being the first product manager at Slack to becoming an executive coach. He emphasizes the importance of sustaining work without burning out and pursuing meaningful goals in startups. This segment sets the stage for discussing the core idea of asking for what you want.
"you were famously the first pm at slack and then you ended up transitioning into Executive coaching for me the impact was about making this work sustain so that we're not burning out or selling out bu..."
The Power of Asking for What You Want
Kenneth Berger explains why asking for what you want is crucial for personal and professional fulfillment. He discusses how integrity plays a role in this process and the consequences of not pursuing what you truly desire. This segment highlights the importance of listening to responses and respecting the 'no's' we receive.
"ask for what you want turns out when you actually ask for what you want out loud you're much more likely to get it you're hired how do you know that this is something you need to be working on if you'..."
The Role of Complaints in Discovering Desires
Kenneth introduces the concept that every complaint implies a dream, encouraging listeners to envision a better future. He discusses how complaints can serve as inspiration for identifying what we truly want, moving beyond fear and frustration.
"Kenneth also shares the story of him being fired three times from slack which is hilarious with that I bring you Kenneth berer after a short word from our sponsors and if you enjoy this podcast don't ..."
Introducing Kenneth Berger
In this segment, the host introduces Kenneth Berger, highlighting his extensive experience in tech and coaching startup leaders. Kenneth's mission is to help individuals learn to ask for what they want, a skill that is often overlooked but essential for overcoming challenges in life and career.
"or YouTube it's the best way to avoid missing future episodes and it helps the podcast tremendously let me tell you about a product called sidebar the best way to level up your career is to surround y..."
Integrity and the Stakes of Asking
Kenneth discusses the importance of integrity in the context of asking for what you want. He explains how many people mistakenly believe they are pursuing their desires while actually fooling themselves. This segment emphasizes the high stakes involved in asking for what you want and the potential consequences of not doing so.
"sidebar ethos when you have a trusted group of peers you can discuss challenges you're having get career advice and just gut check how you're thinking about your work your career and your life this wa..."
Recognizing Stuckness in Your Career
Kenneth identifies signs that indicate a need to work on asking for what you want, such as feeling stuck in your career or experiencing interpersonal conflict. He emphasizes the importance of recognizing these patterns to initiate meaningful change.
"93% of members as sidebar helped them achieve a significant positive change in their career why spend a decade finding your people when you can meet them at sidebar today join thousands of top senior ..."
The Impact of High Stakes on Asking
In this segment, Kenneth explains how high stakes can create fear and hinder effective communication. He shares his experiences as a founder, illustrating how the pressure of success can lead to rigidity in asking for what you want.
"it should be a dynamic part of your strategy that drives convergence that's business 101 but here's a number for you 54% of leaders say web updates take too long that's over half of you listening righ..."
Understanding What You Truly Want
Kenneth addresses the challenge of knowing what you want and offers insights on how to clarify your desires. He discusses the importance of moving beyond people-pleasing tendencies to identify what truly brings happiness and fulfillment.
"Kenneth thank you so much for being here welcome to the podcast yay thanks for having me I love that yay we should that should be a tradition that everyone goes with I love that so we originally met w..."
The Dream Behind the Complaint Technique
Kenneth introduces the 'dream behind the complaint' technique, encouraging listeners to explore their complaints as a pathway to uncovering their true desires. This segment emphasizes the power of reframing complaints into actionable dreams.
"simply asking for what you want which sounds really simple so let me just start broadly just why have you found that this skill this one idea is so core to so many of the challenges that people run in..."
Articulating Your Wants
Kenneth outlines the first step in the process of asking for what you want: articulating your desires. He emphasizes the importance of clarity in expressing what you want and how this foundational step can lead to more effective communication.
"bit right you know when it comes to are we really pursuing the things that we want in life right and I think to me the flip side of that is is sort of the reason that the stakes around asking for you ..."
Iterative Process of Asking
Kenneth discusses the iterative nature of asking for what you want, highlighting the importance of learning from responses. He explains that the process involves not just asking, but also accepting feedback and adjusting your approach accordingly.
"and if we don't do that well then we're kind of fooling ourselves that we're actually moving towards what we want there tends to be all these sort of unexpected secondary and tertiary effects that com..."
Uncovering Your True Dreams
Kenneth Berger discusses the importance of identifying the true motivations behind what we think we want. He emphasizes the need to differentiate between inspiring dreams and unrealistic expectations, encouraging listeners to articulate their desires in a way that feels credible and achievable. This segment highlights the significance of self-reflection in the process of asking for what you want.
"to speak up a little more in meetings it's like well that's probably that's probably not 100% of your dream like what's really behind that and so I think it can it can that check can help you sort of ..."
The Iterative Process of Asking
In this segment, Kenneth Berger outlines the straightforward steps of asking for what you want: articulate, ask intentionally, and accept the response. He emphasizes that while the process seems simple, the real challenge lies in overcoming the internal resistance and fear associated with asking for our desires. This discussion provides insight into the emotional hurdles that can impede effective communication.
"you do is it you dream about what would make you happiest is it like complain and see what's at the root of it is it just imagine a world where you're really happy and see what emerges for you know sp..."
Embracing the 'No'
Kenneth Berger shares his perspective on the fear of rejection when asking for what you want. He encourages listeners to redefine 'no' as valuable feedback rather than a failure, suggesting that anything less than a 'hell yes' should be considered a no. This segment provides a framework for understanding rejection as a part of the learning process in pursuit of one's goals.
"lot of what tends to be tricky about asking for what you want because otherwise it's yeah articulate ask accept okay you're you're getting into where we're going to go before we get there final questi..."
The Power of a 'Hell Yes'
In this segment, Kenneth Berger explains the importance of seeking enthusiastic consent when asking for what you want. He discusses how settling for lukewarm responses can lead to disappointment and unmet expectations. By aiming for a 'hell yes,' individuals can ensure that their requests are fully supported, fostering a more committed and engaged response from others.
"hell yes as a no right and so it's not a bad thing right mostly the world tells us no it's actually really great data it helps us figure out what are we going to try next what are we going to try next..."
Navigating Startup Challenges
Kenneth Berger reflects on the unique challenges faced by startup founders, emphasizing the need to embrace uncertainty and the possibility of failure. He encourages listeners to pursue their desires despite the risks involved, highlighting that the journey is often more valuable than the outcome. This segment underscores the mindset required to thrive in the unpredictable world of startups.
"ready to do this and this applies to you're giving examples here of just like getting hit like a lying a deadline I imagine the same skill applies to everything you in life like relationship questions..."
Articulating What You Want
Kenneth Berger outlines the first step in the process of asking for what you want: articulating your desires clearly. He discusses common pitfalls, such as downplaying needs or expressing unrealistic expectations, and encourages listeners to tune into their true feelings. This segment provides practical advice for effectively communicating one's wants in a way that feels authentic and achievable.
"let's actually get into the skill of learning how to actually say ask for what you want more effectively you already described three steps so maybe just just describe them again and let's just walk th..."
The Importance of Feedback
In this segment, Kenneth Berger emphasizes the role of feedback in the process of articulating desires. He shares insights on how founders can navigate difficult conversations and deliver constructive criticism while maintaining respect for their team members. This discussion highlights the balance between kindness and accountability in leadership.
"Extreme of this is people who you know articulate these sort of you know wildly unrealistic so this is the founder that just wants everyone to agree with him all the time and to obey him immediately r..."
Consequences of Choices
Kenneth Berger discusses the importance of recognizing the consequences of others' choices in a professional setting. He encourages leaders to uphold accountability while fostering a supportive environment. This segment explores the dynamics of leadership and the necessity of addressing performance issues without compromising relationships.
"right because you know I I I work with a lot of Founders who you know are not the sort of classic control freaks right they're super nice right and their teams love them and they love their teams and ..."
Overcoming Fear in Communication
Kenneth Berger provides strategies for overcoming the fear of expressing one's needs and desires. He emphasizes the importance of integrity and mindfulness in communication, encouraging listeners to acknowledge their feelings and articulate them openly. This segment offers practical tips for fostering a culture of honesty and transparency in the workplace.
"enough that they can deal with the consequences of those choices can even get more concrete there is it like we need to hit this date or there's going to be big problems or is it like I need you to hi..."
Intentional Asking
In this segment, Kenneth Berger highlights the significance of intentionality when asking for what you want. He discusses how individuals often fall into comfortable patterns that may not serve their best interests. This discussion encourages listeners to be proactive and deliberate in their requests, fostering a more authentic and effective communication style.
"suggest people do to help identify what it is they want and articulate what they want so you talked about pay attention to just like oh this would be better if like if this changed I would be I'd be h..."
The Power of Articulating Your Needs
Kenneth Berger emphasizes the importance of articulating what you want as a form of mindfulness. He discusses how holding back feelings can lead to suffering and how expressing needs can alleviate that burden. This segment highlights the significance of being honest about one's feelings, even in challenging situations like meetings.
"something that I just I keep thinking about and I'm just like you know three or four days I'm just like man I really want to say this to this person right at this point you're probably out of Integrit..."
Intentional Asking: A Key to Change
In this segment, Kenneth Berger shares insights on the importance of intentionality when asking for what you want. He explains how many people fall into patterns of people-pleasing or controlling behaviors, which hinder effective communication. Kenneth encourages listeners to recognize these patterns and embrace a different approach to asking.
"vanta when it comes to ensuring your company has top-notch security practices things get complicated fast now you can assess risk secure the trust of your customers and automate compliance for sock 2 ..."
Overcoming the Fear of Asking
Kenneth discusses the common fears associated with asking for what you want, including the fear of rejection and the belief that it's not worth the risk. He highlights the importance of recognizing these narratives and the serious costs of not expressing one's desires. This segment encourages listeners to confront their fears and advocate for their needs.
"for for asking what you want I think the really important tweak here is asking intentionally right because I think a lot of us are kind of stuck on a certain track that's comfortable for us when we as..."
The Balance of Asking with Humility
Kenneth Berger explains the balance between asking clearly and maintaining humility. He provides advice on how to express disagreement or preferences in a way that acknowledges the opinions of others while still advocating for one's own needs. This segment is particularly relevant for individuals in positions without formal power.
"right I think that you know we we sort of tend to tell ourselves the story oh this is fine I'll be fine uh versus owning like I'm gonna I'm gonna be living my life like not not asking for what I want ..."
The Influence of Relationships in Asking
In this segment, Kenneth highlights the often-overlooked power of personal relationships in the workplace. He encourages listeners to recognize that their opinions matter and that expressing them can lead to meaningful change. Kenneth emphasizes the importance of vulnerability in communication and the value of sharing gut feelings.
"outcome we want we say oh well I'm not willing to ever piss anyone off ever and so I'm just going to be stuck at this step because like I haven't figured out what's going to guarantee me and of course..."
Embracing Gut Feelings Over Data
Kenneth discusses the tendency to rely heavily on data in decision-making, especially in product management. He argues that gut feelings and personal opinions are equally important and should not be ignored. This segment encourages listeners to embrace their instincts and share their thoughts, even in the absence of data.
"not going to go I'm not going to say this out loud at all but in fact if you're will to say you know like I really disagree with this product decision and like I I would really prefer that we make thi..."
Transforming Complaints into Action
Kenneth Berger shares how complaints can serve as inspiration for change. He encourages listeners to view their frustrations as opportunities to articulate their desires and seek better outcomes. This segment emphasizes the importance of framing complaints constructively to drive positive change.
"your opinion because you believe something uh because you want something often that's enough right because guess what you're in a relationship with these people you work with like they care about you ..."
Validating All Parts of Yourself
Kenneth introduces the concept of internal family systems, discussing how different parts of ourselves can conflict. He emphasizes the importance of validating all aspects of our feelings, including fears and insecurities, to effectively ask for what we want. This segment encourages self-compassion and understanding in the face of resistance.
"more to me complaints are great inspiration um and so I think the you know to to me you know like I love radical cander for example right you know where where where I try to go a step further than rad..."
Embracing Impostor Syndrome
Kenneth Berger discusses the common fear of being an impostor in professional settings and how embracing this fear can help individuals soften their anxieties. He emphasizes that acknowledging these feelings is crucial for overcoming them and recognizing one's true professional identity.
"they're going to find out and then you'll never work again well of course you'd be scared that makes a ton of sense and by embracing that instead of ignoring that and being ashamed to that that is oft..."
Transformative Learning Experiences
Kenneth shares a profound experience from a Stanford class led by Carol Robin, focusing on interpersonal skills and emotional intelligence. He reflects on how this transformative weekend helped him understand the importance of dealing with others and the emotional depth of such experiences.
"impostor syndrome we've touched a bunch of different podcast episodes but I'll avoid going in that direction something you reminded me of is uh we just had Carol Robin on the podcast who taught this c..."
Effective Feedback Techniques
Kenneth introduces a framework for giving feedback effectively, inspired by Carol Robin's teachings. He outlines a structured approach that emphasizes clarity in expressing feelings and intentions, which aligns with principles of nonviolent communication.
"in Tech is the broader umbrella term and Carol talked about it everyone that has gone through it 100% have told me that it's a transformative life experience for them and so and you had a you had a bo..."
The Importance of Factual Communication
In this segment, Kenneth discusses the significance of staying factual when communicating feelings and observations. He highlights how focusing on facts rather than stories can lead to clearer and more effective communication, especially in professional settings.
"I I teach the same thing and yeah I think you know sort of Carol's approach and nonviolent communication uh DBT teaches a similar approach they call deer man um to to me with CBT uh it's a dialectical..."
Accepting Responses: The Final Step
Kenneth elaborates on the third step of asking for what you want: accepting the response. He explains the challenges of hearing 'no' and the importance of emotional regulation in this process, emphasizing that a 'no' does not mean a permanent rejection.
"three I've been we've been going on this whole tangent of therapy and stuff which is amazing but let's make sure we cover all three steps so step one again was articulate what you want step two is ask..."
Navigating 'No' and 'Not Yet'
Kenneth discusses the emotional challenges of accepting 'no' and introduces the concept of 'not yet' as a more constructive perspective. He shares insights on how to view rejections as opportunities for learning and growth rather than definitive failures.
"again right and that's because they get so scared right but actually no like that's over accepting right the no is just from this person right now in the way that you asked right which doesn't necessa..."
Emotional Regulation in Asking
Kenneth emphasizes that emotional regulation is key when asking for what you want. He explains how managing emotions can help individuals better handle rejection and focus on constructive next steps, making the process of asking less daunting.
"more motivating right if someone says okay no I'm I'm not going to I'm not ready to deliver this on time be like okay well I'm going to give the project to another person right like I'm taking your kn..."
Kenneth's Journey at Slack
Kenneth shares his personal experience of being fired three times from Slack, reflecting on the lessons learned from each incident. He discusses how his initial overconfidence and failure to articulate his goals contributed to these challenges.
"doesn't need to be something so scary or awful easier said than than done in real life is there an example of either a clan of yours I know you can't actually share specific details but I'm just curio..."
The Power of Articulating Desires
In this segment, Kenneth recounts how he learned to articulate his desires after facing multiple rejections at Slack. He highlights the importance of expressing what you want clearly and how this can lead to better outcomes in professional relationships.
"times together so they wanted someone to come in Humble and to kind of earn their trust of this kind of core team that had been together for years and so I you know I just didn't get any of that right..."
Overcoming Impostor Syndrome
Kenneth reflects on the ongoing struggle with impostor syndrome during his time at Slack. He discusses how fear and insecurity affected his performance and relationships, and the importance of addressing these feelings to foster a healthier work environment.
"terrified right of like you know was I going to get fired right was I going to not you know make the most of this opportunity and so you know I went fully into people pleaser mode and so that meant th..."
Integrity and Authenticity in the Workplace
Kenneth concludes by discussing the significance of maintaining integrity and authenticity in professional settings. He emphasizes that being true to oneself and articulating desires is essential for personal and professional growth.
"know and and so you know that what what I think what what I couldn't be with in that moment was was the NOS right because I was getting no after no after no after no you know from from Stuart and the ..."
Lessons from Failure
In this segment, Kenneth discusses the consequences of not listening to feedback and the emotional struggle that ensued during his time at Slack. He highlights how his inability to articulate his needs and accept rejection contributed to a year of personal turmoil. This reflection serves as a cautionary tale about the importance of integrity and self-awareness in the workplace.
"not listening to the nose you know I shouldn't have been surprised when finally the third time it came down and this time it was serious because we had HR so it turns out once you hire HR the firings ..."
Integrity Over Outcomes
Kenneth emphasizes that asking for what you want is not just about achieving specific outcomes but about maintaining integrity with oneself. He reflects on how his past mistakes taught him the value of honest communication and the need to prioritize personal alignment over fear of failure. This segment encourages listeners to embrace vulnerability in their professional lives.
"much a lot of people suffer in these similar circumstances and all you have to do to turn it around is ask for what you want so this is why I'm so passionate about this stuff because it sounds so it c..."
Navigating Founder Relationships
Kenneth shares insights on the critical relationship between a product manager and the founder of a startup. He discusses the importance of understanding the founder's perspective and the emotional challenges they face. This segment provides valuable advice for new PMs on how to foster healthy working relationships and navigate the complexities of startup dynamics.
"so passionate about this stuff wow what a story and I love that it's kind of a microcosm of everything we've talked about you've kind of did all the things that you teach people to avoid exactly and I..."
Asking for What You Want
Kenneth reflects on what he would have done differently during his time at Slack, emphasizing the importance of asking for what you truly want. He discusses the potential outcomes of such requests and the necessity of staying true to oneself, regardless of the fear of rejection. This segment highlights the transformative power of clear communication in achieving professional fulfillment.
"because an early stage startup right like there wasn't a ton of sort of process or structure in place suffice to say and so if I wanted that I needed to create it myself but because I hadn't articulat..."
The Role of Fear in Motivation
In this segment, Kenneth addresses the common belief that fear is a necessary motivator for success. He challenges this notion by suggesting that individuals can find inspiration and motivation through joy and vision instead. Kenneth encourages listeners to explore alternative ways to drive their ambitions without being hindered by fear, promoting a healthier approach to personal and professional growth.
"of the world and I think that mistake we make is pretending that it is right of saying you know going into fight or flight and saying this is like a severe existential threat to who I am and sort of m..."
Contrarian Views on Discipline
Kenneth shares his contrarian perspective on discipline, arguing that it is often a short-term coping strategy rather than a sustainable approach to achieving goals. He emphasizes the importance of intrinsic motivation and finding joy in the work rather than relying on external pressures. This segment invites listeners to rethink their relationship with discipline and consider more fulfilling ways to pursue their ambitions.
"our core topic is there anything that we didn't cover anything that I should have asked you about the skill the art of asking for what you want anything else you want to leave listeners with I I do wa..."
The Myth of Discipline: Seeking Sustainable Motivation
In this segment, Kenneth Berger shares his contrarian view on discipline, arguing that it is an unsustainable approach to achieving long-term goals. He explains that while discipline may yield short-term results, true motivation comes from a genuine desire to pursue one's interests. Kenneth advocates for finding deeper, sustainable motivations that align with personal vision rather than relying on external pressures.
"short of it amazing we I it reminds me we have a chat I had a chat with Matt mashari and we spent a bunch of time on dealing with fear and overcoming fear so folks want to dig deeper there they could ..."
The Power of Asking: A Life Motto
Kenneth Berger reflects on his core life motto: 'Ask for what you want.' He emphasizes the significance of this principle in both personal and professional contexts, encouraging listeners to embrace the practice of articulating their desires. This segment encapsulates Kenneth's passion for helping others navigate their aspirations and the importance of open communication in achieving success.
"you get I I am a broken record admittedly amazing uh Kenneth is there anything else you wanted to share or leave listeners with before we get to our very exciting lightning room no but just thank you ..."
Book Recommendations for Personal Growth
Kenneth shares his favorite book recommendations that align with personal development and leadership. He highlights 'Radical Candor' by Kim Scott, which emphasizes the importance of direct communication while caring personally. Kenneth also mentions 'The 15 Commitments of Conscious Leadership,' which provides actionable guidance for living a fulfilling life, blending deep insights with practical advice.
"recommended most to other people well I already mentioned radical cander I think that is for sure a modern classic um and I think that that whole idea of sort of challenging directly but caring person..."
Finding Inspiration in Tennis and Film
In this segment, Kenneth discusses his newfound passion for tennis and how it parallels personal development. He shares insights from the Netflix documentary 'Breakpoint,' which explores the mental challenges faced by top players. Additionally, he reflects on the film 'Living,' which portrays a man's transformation as he confronts his mortality and seeks to leave a meaningful legacy.
"love the uh 15 commitments of conscious leadership um so I I I'm pretty sure other guests have mentioned that as well but to me part of why I like that is that I think a lot of personal development bo..."
Exploring New Interests: The Journey of Tea
Kenneth shares his recent exploration of tea as a healthier alternative to alcohol. He discusses the benefits of Taiwanese oolong tea, highlighting its positive effects on focus and well-being. This segment illustrates Kenneth's journey towards healthier lifestyle choices and his enthusiasm for discovering new interests that contribute to personal growth.
"everyone is kind of the same because all these people they all know all The Strokes perfectly like they're technically perfect in pretty much every way and so it really is mental right for those folks..."
Engaging with the Community: Building Connections
Kenneth emphasizes the importance of community engagement in his work. He invites listeners to connect with him on LinkedIn and subscribe to his newsletter, where he shares insights on asking for what you want. This segment underscores Kenneth's commitment to fostering meaningful relationships and creating a supportive environment for personal and professional development.
"last months of my life and he he builds this playground for children and that's actually his his legacy sorry actually spoiler alert whoops J uh you mentioned tennis and you mentioned British people u..."
The Journey of Writing a Book
Kenneth discusses his ongoing journey of writing a book titled 'Ask for What You Want.' He expresses his desire to share actionable strategies for personal growth and emphasizes the importance of community feedback in refining his ideas. This segment highlights Kenneth's dedication to making a positive impact through his writing and coaching.
"motto that you often come back to find useful share with work share with friends or family in work or in life I mean I'm pretty sure you can guess weny I wonder what it might be I wonder what it might..."