Self-Leadership: The Key To Achieving The Good Life With Lenny Richardson
There probably isn’t one person on this planet who doesn’t want a good life. It might mean different things to different people, but ultimately, we all want what we think is good for us and what we think we deserve to have. How does that happen? Today’s guest believes that it’s all about self-leadership. Lenny Richardson argues that to achieve “eudaemonia”, you have to hold yourself accountable for setting a vision, having a destination in mind, and guarding yourself against the temptation of procrastination. Join the conversation as Lenny dishes out piece after piece of wisdom that you will surely be able to apply, no matter what industry you’re in and what stage of your career journey you’re at. Tune in!
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Self-Leadership: The Key To Achieving The Good Life With Lenny Richardson
Welcome to Episode 26 of the show. This is the show where you hear the real stories of normal people like you who have become extraordinary leaders. You’ll learn some valuable lessons from their lives. Lessons you can apply to become the best leader that you were created to be. When you become an intentional leader, lives are changed. I’m your host Sean Olson. I’m an Executive Coach, Business Owner, Author and Speaker. Thank you for joining us.
For all of you joining us, our readers, you’ve read before through all of your favorite platforms, but this is our first ever video episode also running through on YouTube. Welcome to the video portion of the show. Our guest is Lenny Richardson. Lenny is a productivity coach. He has an incredible story and he has an incredible leadership lessons for us. Lenny, welcome to the show.
I appreciate you for having me on. This is a this is pretty cool to be the first video episode so I’m excited.
I’m glad to have you and have you as the first video one. This is a stretch for me because I’ve always said, “I have a facement for radio,” but now we’re going to expand a little bit. We’re in the video side into it. Lenny, you know our show and you know that we begin every show at the same question and hearing your professional journey. What you have learned in that journey about leadership and we’ll have a great conversation. I know your story is a powerful one. Fill us in on, Lenny.
A Powerful Story
I’ll try to not be super long-winded about this. To go back, to start off, Penn State as a student. Initially, it was more or less a typical college journey. Eventually, one day I got this letter in the mail and it said very nicely, “Don’t come back. You’re not allowed to come back to school and take classes here.” I got kicked out. It wasn’t for anything super bad. I’ve seen kids who get kicked out for things like drugs and academics things of that nature.
It was nothing like that. It was just finances. I owed a few grand for tuition and the school said, “You don’t have the full balance paid. Come back when you do.” That was a bit of a struggle at the time. The most jobs I’ve had was I was a volleyball coach in high school for 8th graders, but I never had an actual job. I didn’t know anything about budgeting. I knew nothing about finance and even paying my own rent at the time because I had been living on campus with loan money and my parents paying for it.
To have to leave school so abruptly. I got the letter in December of maybe 2013 or 2014. It was abrupt. I ended up doing a bunch of different jobs to pay rent. I worked at a gas station, movie theater, and Walmart for a brief period of time. I worked as a dishwasher and a busboy at this Irish pub called Kildare’s, which no longer exist in Penn State, but if for anyone that’s reading that may have gone to Penn State years ago. I think they got knocked down years ago. They’d be familiar with it.
I did that and that’s what started. It helped me think about leadership because when you work so many different jobs, in my personal opinion, you get to see what a good leader is and sadly, a bad leader is sometimes. I’ve had some jobs where you get a supervisor and to put it bluntly, they don’t care about you as the individual working with them or working for them. You get some bosses or some managers or supervisors who are fantastic. They’re very accommodating and supportive. That’s the first step. That’s me trying to make a long story short. Hopefully, that answers the question.
Self Leadership: When you work so many different jobs, you get to see what a good leader is and, sometimes, what a bad leader is.
That was a huge shock like you can’t get back to school now. I was laughing because you talked about, “I did this, this, and this these jobs,” but you’re grinding in and out. There’s a lot of people who would take that shock to their system of being kicked out of school because of finances, play the victim, sit back and complain about it. You picked yourself up and started doing the grind. What was that?
What was it as far as?
In you that made you go that way.
I didn’t have a choice because my parents weren’t paying for my rent. At the time, my rent wasn’t even that high. I think it was about $500 a month because I had roommates but I didn’t have a job. I went out and found the first few things I could find. The first job that hired me was a gas station called Snappy’s but they’re paying $7.50 an hour. The sad thing about jobs like that sometimes people don’t consider is if you work one of those low-wage jobs. You don’t always get full time. Sometimes they give you 20 hours a week or ess than that. Maybe sometimes more than that.
By the end of the month, you see your paycheck. You’re making $7.50 and worked 20 hours a week. You’ve made about $500 once taxes takes it all away. It’s like, “I need a second job because this isn’t going to work and I need to eat.” I truly think it was necessity. I don’t think I had much time to think much about it. It was just I need money now to pay for rent. My parents helped me with the down payment to start renting but they weren’t helping me pay the monthly rent. That was on me.
You got those jobs started working through. Now pick up to what’s the rest of the story? What brought you to what you’re doing now?
Eventually, I graduated and started working at the suit store. It was a suit store called Brooks Brothers, if anyone was familiar with that franchise. Again, it didn’t pay that much and at this point, I have to pay for student loans. You have to pay for rent outside of college because I moved to Northern Virginia, which is very expensive area.
I didn’t know about the time but it’s a very expensive area. From Brooks Brothers, ended up getting my real estate license. I did real estate on the side. While doing real estate, I also got hired at a law firm which I can’t take any credit for getting that job at the law firm. The most I did was apply because I needed more money because Brooks Brothers wasn’t paying the bills. They liked me and I had a website at the time from back when I was in college. I had a small business called College Conqueror that I tried to get up and going didn’t go as well as I’d hoped.
They saw that and they liked it. They liked me and hired me. I did the law firm full-time and the real estate side. One thing led to another, I started my own business called Affinity with a business partner. We did that for a few years. It was going well at first then differences between me and the partner cause it to split up. We split up and end of the business.
Leadership And Self-Leadership
From doing real estate, I started to do personal branding because I thought it was effective for real estate agents to market themselves, but I didn’t want to just do real estate personal branding. My marketing philosophy with this is people like people and you have to talk about just your philosophies. My main philosophy was this idea of eudaimonia, which is the good life. People strive for health, wealth, and relationships.
This is a concept that stumbled on back when I had first got kicked out of college. In my opinion, it’s a concept that’s always pushed me to want to do more things. It’s helped me maintain focus when it comes to my goals, dreams, and vision. That’s the thing I started to talk about more. Ultimately, I figured real estate is good but the downside about real estate, at least as an agent, is you’re stuck in one location doing real estate. I figured, “Let me try to help more people with this idea of eudaimonia.” I tried doing that and doing coaching with that.
I had a few clients, but the issue with it is that it was too many different concepts. I tried to get people to do all three into two short periods of time. The thing that everyone needs, at least what I found to get to you eudaimonia, is you need time management. You need productivity. You need to know how to manage yourself effectively. Once you learn how to manage yourself, then you can work on your fitness if that’s your priority or then you can work in your finances or your relationships.
Let’s break that down a little bit. That’s eudaimonia for those you think about eudaimonia. It means the good life. You talked about the three elements of that health, wealth, and relationships and we’ll get to that. Let’s focus first on what you said before you get to health, wealth, and relationship. It’s about you in perspective and that self-leadership. Talk about that a little bit what that means for you and how you’ve coached other people to that.
For me, self-leadership is that the idea of being disciplined with oneself. I’ll put it this way, to be an effective leader, you have to know where you’re going. You have to have a plan. I like to study history and what I think about history, the best leaders people like. I know people get a bad rap. People like Napoleon and people say like Alexander the Great. They’re leaders but the thing that makes some such compelling leaders and such influential leaders is that they have a vision.
They know where they’re going. They can manage themselves, but they can also manage others to help them get whatever it is that they want out of life. If you’re one of Alexander’s followers, what you wanted out of life was to be known as someone that supported Alexander on his goal. Fair enough, that’s your goal. If you work in a business, I’ve heard this a lot from people my age. People who are Millennials.
“What sets influential leaders apart is that they have a vision. They know where they’re going, they can manage themselves, but they can also manage others to help them get what they want out of life.”
They’ll say they want to work at a job where it’s not always about the money. The money is necessary, but it’s not feeling like you’re making an impact or you’re achieving something or doing some greater good. As a leader, you have to figure out what people want and know what you want. It’s simultaneously get people to do both because the reality is to be a leader, especially an effective leader. It’s not east, but it’s not common. It’s very rare to be a leader.
I like everything you’re sharing there. This is called the Intentional Leader, so what you’re talking about there's got to be intentional about it. It’s not going to happen for you. There are a lot of people that sit back. You’re describing, you’ve had good bosses and bad bosses. We’ve all been there. If you’re with a bad boss now, it’s very easy to sit back and say, “What was me,” versus, “I’m either going to keep doing the best that I can here in spite of that boss or find a different place to go and get a good one.” Everything’s intentional with it. That’s where I even like your story, the grind of going after job then real estate and Affinity with a friend and developing that. You didn’t sit back and say, “Why isn’t everybody helping me or what’s going to happen?” You said, “I got to go.”
It sounds weird but that idea of doing things and trying to push forward in life, have at least some destination in mind. At its core, that’s what makes someone a leader. This might sound controversial, I don’t think most people have that. Most people do, if they were to try to admit it or sit there and think about it. They allow everything else around them to push them to do something. I’m not saying that’s a bad thing.
That can be a fantastic thing, but most people are probably more followers. There are few people that are leaders. You have to figure out which one would you rather be, because to be a follower is a bit easier. That’s just me being biased. To be a leader is difficult, but there’s more responsibility. There’s more effort, work and more you have to keep in mind when you become a leader. You have to pick and choose. It’s like being a CEO or a boss of a company. There’s more risk, but there’s more reward if things go well.
Self Leadership: Being a follower is a bit easier. Being a leader is difficult. There's more responsibility. There's more effort. There's more work.
What I like them about your sharing there is, I don’t know if you meant to do this now, but I was hearing two different things. Even if you’re a follower at work, if you don’t have a leadership position, you still need to lead yourself. You take the reins and control because no one cares about your career as much as you do. No one cares about your health, wealth, and relationships as much as you do. Self-leadership exists whether you are an individual contributor or a leader at work or not. You still got to jump on and be intentional about yourself.
You have to be a leader of yourself. There’s a saying. I’m going to completely mess up the saying. It’s something along the lines of, “If you don’t give yourself a purpose or a vision, society will give you one instead.” You have to be a leader of yourself, give yourself a vision, a plan and a destination that you want to go. Otherwise, you’ll either not go anywhere at all, which I don’t think people would want to do. Most people want to go at least somewhere positive. The other outcome is that society or things around you will give you a destination. It might not be the best destination for you.
“Be a leader of yourself. Give yourself a vision. Give yourself a plan. Give yourself a destination. Otherwise, you’ll either not go anywhere at all, or society will give you a destination, and it might not be the best destination for you.”
Getting The Good Life
That spans a lot of different realms, too. You talked about personal brand a little bit. You have a rant no matter what. The question is, are you creating what that brand is? Are you going to let them create it for you? When we work with organizations, the organizational culture. If you don’t intentionally create the culture for your company, they’re going to create it for you because it’s going to exist no matter what. Those things play out.
Let’s talk about eudamonia for a minute, the good life and the three key elements. Those three words of health, wealth, and relationships sound self-explanatory. It sounds to me like it’s not an order. You have to take it in the order that’s best for you but go a little bit deeper on all three of those elements and what that means for the good life.
When it comes to eudamonia, first of all, it’s this old Greek philosophical concept. I believe people claim Socrates came up with it, but Socrates never wrote things down. He dictated to a student and Aristotle coined the term for Socrates. He began to write it down, but basically, it’s a framework of how people or at least how Socrates believe people should live their lives to have the best quality life possible.
Health, you need to be in good shape. If you hear health, it’s not just looking good because people will assume health is like aesthetics and that’s not it. It’s mental health and being in decent shape. Good enough shape. You want to be functional. You don’t want to be someone who maybe struggles to walk or someone who is sickly, if you can help it.
Genetics things play a role in that but if you can help it, you don’t want to be in that position. Wealth, you don’t need to be rich but you want to live below your means. You want to be financially secure. You don’t want to be in a position where you have to do things that you might not want to do like me back in the past with the jobs that I didn’t particularly like just because you need to pay the bills.
Part of that too is financial education. You have to know a little bit about finances to make sure you’re not a bad position. Relationships is the romantic part of it too, which when people hear relationships, that’s what they default to. A relationship between a partner, but it’s also your social relationships. Do you have a good circle of people that uplift you, positive, or interested in the things you’re interested in? Do they support you? Once you combine those three things, as far as Socrates was concerned. The combination of those three things is what will give someone a higher quality life, the good life, so to speak.
I like that. It plays out. As a productivity coach, give us a glimpse at what you’re doing with your clients. Are your clients people that are feeling like they’re at the bottom and they need to be picked up? Are they clients who are doing well, but they want to do excellent? Talk about who your clients and how you are coaching them. What’s that look like?
It’s a bit of a mix. I haven’t had anyone yet that feels like they’re at the bottom. Usually, it’s young professionals or people who are just getting into the professional world and they feel scattered. I’ll give you one example. I had someone, he’s starting a real estate development company. He also wanted to get in shape. He felt like his daily structure wasn’t there. He was already doing things but he wanted to tighten it up and make sure that he was getting in enough time to go to the gym, to work on his business, and to be different.
In his case, real estate agents because he thought real estate agents would help him sell some of these, I don’t say units because they weren’t units but buildings that he was to develop. It depends. I haven’t had anyone that’s low. It’s usually people who feel that they don’t have a lot of structure in their lives and they want to create more structure.
Most of them, it’s more structured toward the financial side. I think that’s completely fine. I’ve had no one yet that’s been super interested in the social aspect, which I find interesting now that I’m talking about it. It’s usually young professionals that want to get more done every single day. They feel like they’re procrastinating or not focusing enough.
You’re finding common themes that’s holding them back.
The number one thing that I always see is procrastination. People procrastinate and I get that. That’s a normal thing. I find that a lot of times they come in and they want to do A, B, and C but they’re not doing A, B, and C. The very first thing I do, we sit there and figure out what are your long-term goals. The first practical thing I make them do is get a planner and try to get into the habit of planning things out the night before. That’s just my personal suggestion.
The main reason is if you plan things out by the hour from the moment you want to wake up and from the moment you want to go to bed. If you do that and you do that the night before, you wake up knowing exactly what you want to do that day. I found and this is what they’ve also claimed when they try to do this, you feel guilty if you don’t get those things done.
Usually, what I tell people if you’re brand new to this, don’t try to put like a thousand things in your planner. I don’t think that’s the best way to go about it if you’re brand new to trying to structure your day. What I tell people is figure out what the top 1 to 3 things are that you believe or that you know will help you get to whatever goal you have.
Plan your day out so that way at least that top one thing is on the planer. The very first thing or as early as you can get it in on your schedule. If nothing else, make sure that one thing is done. That’s it, because a lot of people they struggle with procrastination and organization. When it comes to the whole procrastination, I usually find that the top two reasons people procrastinate is because they either don’t know how to do something or afraid of the outcome. That fear of the outcome keeps them from starting or getting things going.
Self Leadership: The top two reasons people procrastinate is because they either don't know how to do something or they're afraid of the outcome.
The planner solves that. If you don’t know how to do something, that’s easy. You can go look it up or you can talk to someone who has done something. If you’re afraid of the outcome or afraid to start because you don’t know how things are going to go. Putting it on the planner forces you, “I need to get it done because if I don’t get it done, it’ll feel worse to reflect on it and realize that I’m not making progress.” Objectively, the planner will show you made no progress. You put one thing on your planner and you didn’t even do it. Now you have to do it. The terrible guilty feeling and it’ll be in your face. You can’t ignore it because you’ve written it out.
I like both sides of that feeling, though. I like the fact you’re saying doing daily, so at night time. Read it out for the next day. You’re not saying write out the next two weeks. It’s write out the next day. What I like about that is, if I don’t accomplish it at the end of the night, I might feel guilty and unfulfilled. Whatever word you might want to use.
I’m also then sitting down to write out the next day and I can put it back on there. It’s like, “Maybe today was not a failure. I just didn’t get it done. I feel bad about it but tomorrow’s a new day. I can go after it.” That feeling doesn’t have to linger with me. It’s not going to pull me down. I’m like, “I got to go after it get it done.” You said a lot of us around the financial piece. They’re obviously struggling to get a hold of their finances and whatever realm. What are you finding are some of the common tips you’re giving these people to get a grip on their finances?
Usually when it comes to the finance thing, it’s more so they’re maybe someone trying to start a business. They’re trying to go from here to here. I’ll give you an example. I had someone, he’s a copywriter. He’s been trying to get different agencies to hire him as a copywriter. We went through a schedule. I remember for months, I told him based on what he’s discussed with me on how he’s acquired agencies to work with. The thing he needs to do the most is reach out to more people. It’s just a pure volume thing, which sounds simple to a lot of people. It is simple and yet, most people when told you know, “If you need more leads probably just reach out to more people.”
They don’t do it because there may be afraid of something. It depends on the individual. In his situation, it wasn’t that he didn’t have any money. He wanted to get more agencies, but he’s also comfortable. I remember, we sat there and I said to him, “What you need to do is do nothing else for the next week besides outreach. Don’t do it all day. Take two hours and only do outreach. No YouTube. No music with lyrics.” He did it.
The first week he tried it, he got 2 or 3 new agencies he worked with. This is after about eight months of him not making any progress. For a lot of people, it’s simplifying what they’re doing. Probably finding the few things that are going to get the progress then just doing it. It sounds so simple and it is simple, but I don’t know. It’s one of those things where a lot of things in life to me are very simple, but people just don’t do it.
It’s procrastination. There’s a lot of reasons behind it. It’s interesting it made me think of a conversation I had with the person. They basically looking back at their past year and they didn’t accomplish everything they wanted to accomplish and just simply said why. They’re like, “I sat down and I was thinking about it. I just waste a lot of time. I’ll jump on social for a while then I’ll go do this for a while. My neighbors outside, so I go talk to my neighbor for a while.”
It’s a work from home situation. There’s in some senses more distractions that are present there. I said, “What are you going to do different?” He goes, “I got a buckle down and just realized that I’m wasting time on those things. I can be more productive.” He’s in a commission world, too. If you’re not doing it, you’re not going to get paid for it. It comes back to that idea and you said this word the very beginning of our episode about discipline.
Self-Discipline
The Intentionally show, I call it intentionality too. You have to be intentional about all that you’re doing to be disciplined in it. When we have discipline and we’re intentional, that’s when we get the fruits of our labor. It’s not just going to happen for us. You’re doing a lot of different things so. How does Lenny keep himself disciplined to be doing things he should be doing?
“When we have discipline and when we’re intentional, that’s when we get the fruits of our labor. It’s not just going to happen for us.”
I do the exact same thing I share with clients. Every night, I sit there and I plan my day. I try and this might be a little bit different than what I would share with the client. I try to pack in as much as I can because I like to work as much as I can throughout the day. Once I start to feel tired, that’s when I stop. Over years, I don’t feel guilty about not getting certain things done. As long as I get the main things done, I’m happy.
Over the years, I’ve built up a habit of being relatively disciplined. There’s some days where I fall off and I intend to do A, B, and C and I get nothing done then you have to reset there. I feel the guilt, too. The next day, get back on the wagon and try again. As far as discipline, it’s a habit now. I try my best to do things and not make excuses for myself. Stick to the planner and try not to overwhelm myself.
Personally and other people probably have felt this, if you overwhelm yourself too much or if you get to that burnout state. You create this negative association with things like work or trying to accomplish a goal. That’ll also prevent you from doing it or trying to do it. I’ll give an example. Me and some friends were talking about this.
I like to work out as well and a friend of mine wanted to get in the gym. He’s asking me about a workout routine and how I can help him. I said to him, “I’m not a trainer but I’ll give you what could help.” I gave routine and I worked out with him just to show him the workouts and make sure he’s doing it correctly. He wanted to work out for about two hours and this is someone who does not work out at all. It’s a very long time and he was excited.
He’s like, “Let’s do cardio. Now, let’s do it. Let’s lift this.” I said to him, “You don’t want to do too much too quickly because you feel enthusiastic now because it’s brand new. Maybe you see a vision of yourself where you’re in super good shape and that’s fine. That’s fantastic but the issue is that if you do too much too soon, you’ll burn out.” This applies to productivity and discipline as well. Physically, you’ll burn out when it comes to weightlifting. In about 2or 3 days if you keep the same pace, you’re going to feel too fatigued and too exhausted then your brain is going to associate this negative feeling with you working out.
Self Leadership: If you do too much too soon, you'll burn out.
The next time you go to work out, you’re going to think to yourself, “The last time I worked out it sucked. I was sore. I couldn’t walk well. I felt super sick.” I’ve seen some trainers when they work their clients too much, the point where they throw up. I don’t know why people do that because now, in that person’s mind are thinking, “The last time I worked out I threw up.” I don’t think anyone likes throwing up. They’re not going to work out anymore because they’re going to associate exercising which can be good for you with throwing up which is usually not a good sign.
The same applies to trying to be more disciplined or getting more done. You don’t want to do too much too soon. You want to take things easy enough. Over the years, to shorten this up, that’s what I learned to do for myself. I created a habit because I don’t push myself to do too much. I do enough or what’s moving me in the direction that is a good direction and I stop. I allow myself to feel good about what I have done.
I like that. You use a word habit a number of times and that’s one of the keys to it. Even with the nightly planner, I don’t remember the exact thing. They say, “If you do something 28 days in a row, it begins to become a habit.” A month of that develops that habit and if it’s putting out what’s a modest goal for the day, what are things I want to accomplish, then I start developing that rhythm of feeling good about it. It’s like, “I can do this. This is going to work out well for me.” I love those things. Lenny, it’s been good to have you today. We finish every episode with the same question. That question is, what is something our readers can do intentionally now to lead more effectively?
I don’t know if it’s going to be well received or not but the thing most people can do to become a more intentional leader and a lot of people don’t do this. I’m guilty of this myself, is listen more. I know that might sound strange but when I think of the word listening, there’s a difference between hearing, which a lot of people do and listening, which is there’s more aspects of listening. You can take this if you have a girlfriend or boyfriend or you’re in a leadership position of any kind. To me, listening is you hear what the person saying.
You tailor what they’re saying based on who the person is. You’re also watching out for the way they say something. An example I like to think about when about listening is, I use my own girlfriend as an example. Sometimes, my girlfriends talkative. She likes to talk a lot, which is the good thing. She sees this. I’m not saying that in a bad way but I can tell when something’s wrong with her.
If I hang out with her for a day and she has said nothing or very little. I say to her, “Babe, what’s wrong?” She says, “Nothing’s wrong.” Meanwhile, she doesn’t want to look at me. Her arms are crossed. She hasn’t been talking the entire day. To me, that’s listening because she verbally said nothing’s wrong. If you were to only hear what she said, you’re going to miss the nuance of everything where she hasn’t been speaking all day. Clearly, something must be wrong because that’s not normal for her.
She said, “I’m fine or nothing’s wrong,” and yet she barely wants to look at me. She’s turning to the side. She’s mumbling the way she says it. That’s, to me, with listening means. I feel like I’ve worked with people or I’ve had managers where an employee might say, “I don’t like how this is working out.” That’s a more blunt thing to say, but the manager or supervisor might hear it and say, “Work on that,” then nothing gets done.
“Listen first. Listen to understand.”
You don’t listen because now the persons vocalizing that they’re upset. They want you to do something and maybe they’re more upset than they’re letting on but you’re not listening. You’re just hearing them. Maybe you do something small to maybe you think that makes them happy in the short run but you haven’t solved the problem. You haven’t investigated to figure out what the problem even is because you’re not listening.
I love it. great tip. Listen first and listen to understand. Lenny, it’s been great to have you on the show. For listeners, there will be some links if you want to go to Lenny’s website and follow up with him on some of his social. Lenny, I pray you have a blessed good life.
You as well. I appreciate you having me on. It was a good time.
Important Links
Lenny Richardson - LinkedIn
