From Me To You Part 2: 35 Lessons That Have Helped Shape Me

Apr 9, 2021Motivation0 comments

Welcome to week two of our month-long series, where I am sharing the cumulation of some of the most meaningful lessons which have made me a better version of, well, me. 

Some of these perspectives and ideas may resonate with you; some may not. Some you may have encountered long ago, and some may be new concepts to you. Either way, I encourage you to read on and see what you can take away for your journey. 

Lesson #8: We leave behind effects in everything we do and every interaction we have.

The effect of our work is results. In the same way, we leave the effects of our interactions with people in their hearts, minds, and souls. No matter where we are, what we’re doing, or who we’re with, we should always be conscious of the fact that our words, interactions, and actions leave lasting impressions.  

When you approach your work and relationships with this filter, you’re more likely to achieve success. It doesn’t mean everyone will like you. But, others will view you as positive and authentic, two qualities that will attract the type of work, clients, team members, friends, and relationships you can thrive in and with.  

I remember one of the first clients I took on as I started Raine Digital. A friend of mine wanted to introduce me to her boyfriend, who started his own business and needed help with his branding and website. I didn’t know it at the time, but it turned out to be someone I had gone to elementary school with.  

The three of us met over dinner. When I arrived at the restaurant, I immediately recognized this person I’d gone to school with. We had been friends until the fourth grade when his parents got divorced, and he moved away. When he told all of us at school, my fourth-grade self had an outburst. I explained to him that “I didn’t care” and that “he was never really my friend, anyway.” Harsh–I know. I, of course, didn’t remember it quite that way, but I don’t doubt that interaction happened. In hindsight, I can now see that reaction was my defensive, childish response to protect myself from the emotions I was afraid of (or perhaps didn’t even understand). Unfortunately, that hurtful memory of me stuck with this individual for the following two decades. It was the first story they brought up at the dinner table.

That single interaction overshadowed the few years of elementary school friendship we shared and lasted long into adulthood. I, of course, felt terrible and apologized profusely, explaining where my response came from as a child. Thankfully, we were able to laugh about it, and he’s still a thriving client to this day.

My point is this: if an interaction like that can leave an impression for decades, what kind of impressions do you think your day-to-day interactions with others are leaving? Consider your interactions throughout the day. With prospects, colleagues, those you manage, and those who lead you. What kind of remnants are you leaving behind?

Lesson #9: No one is above the power of influence.

You’ve probably heard it said, “Show me your five closest friends, and I’ll show you your future,” or something to that effect. There is so much truth in this statement. Our circle of influence is just that–a circle of people, friends, family, and co-workers that influence our lives and vice versa. 

This is why it’s mandatory to be cautious about whom we let into our lives. The type of people we engage with have a direct impact on our well-being. I believe we should have three groups of people in our lives. The first are people whom we look up to. These are the people who have done or accomplished things we admire, and we know we can learn from them. A mentor of sorts, if you will. They could be authors of books we’ve read or people we have a relationship with. 

The second group of people I believe we should all have in our lives is our peers. These are the people we would consider to be in our inner circle. This would include your significant other, friends, family–you get the idea. The people we do life with.  

The third group of people we should have in our lives are those we teach, share, and give back to. The people who come to us and ask, how did you do that? Can I learn from that? These may be people who are up and coming into a career you’ve already found success in or those looking for solutions to problems you’ve already figured out how to solve. 

Above all, I believe that the people we surround ourselves with should be the kind of people who pour water on the fires of our fears and gasoline on the passions of our dreams. In turn, we should be that kind of person for others.

Lesson #10: Fear is paralyzing. Sometimes you just gotta do it scared.

There are many things I know I’ve missed out on in my career because of some sort of fear. Most of the time, it was fear of the unknown. Sometimes it was fear of failure; other times, it was fear of living up to the demand and expectation of an opportunity. Here’s the thing though, if you let it fester, fear becomes paralyzing. It will keep you from where you need to go.  

Of course, I have to put the disclaimer here that there is such a thing as a healthy fear. The kind of fear you want your child to have about touching the hot stove. The sort of fear that protects us from the things that are guaranteed to harm us.  

If we can learn to identify the healthy fear, we can begin to face the unhealthy fears limiting our potential.

I really enjoy what Will Smith has to say about this: 

“Fear is not real. The only place that fear can exist is in our thoughts of the future. It is a product of our imagination, causing us to fear things that do not at present and may not ever exist. That is near insanity. Do not misunderstand me, danger is very real, but fear is a choice.”

I hit a point in my career where I realized I would either plateau where I was or I would have to face my fears and start doing some things that scared me. The thought of how to take this leap of conquering fears troubled my mind often. 

On one of my travels, I discovered this gem entitled Do It Scared by Ruth Soukup. It’s designed to be a workbook that encourages you to do one thing every day that scares you. Some days, that fear was as small as confronting a team member. Other days it was standing up for myself and my beliefs. Another day it was the first time I had to fire someone. Then came the day I needed to take on my first ever public speaking event (which I was truly terrified to do).  

One of the most significant parts of this experience was that I continued to find I had far more in me and was much more capable than I ever knew. This act of conquering fears day by day was a huge growing experience for me. Sometimes, you just have to muster up the courage to start slaying your fears–big and small, one day at a time.

Lesson #11: Cocky versus confident–it’s a fine line. 

Let’s look at the definitions of these two terms:

Confidence is “a feeling or belief that you can do something well or succeed at something.” 

On the flip side, cocky is defined as someone who is “boldly or brashly self-confident or arrogant.”

Sometimes it can be hard to differentiate between the two, especially when you first meet someone. Confidence and cockiness can look a little different depending on the person and their personality, but here are a few key differences between the two:

  • Confident people tend to let their actions speak for themselves.
  • Cocky people tend to be insecure and try to make up for that by talking about how good they are.


  • Confident people aren’t afraid to own and learn from their mistakes.
  • Cocky people will try to conceal, twist, and cover up their mistakes.


  • Confident people are happy to give credit where credit is due.
  • Cocky people try to take all the credit for themselves.


  • Confident people aren’t afraid to admit a weakness and ask for help.
  • Cocky people often feel like asking for help is a sign of weakness or incompetence. 


  • Confident people are secure in their accomplishments, with or without recognition.
  • Cocky people often require constant praise, whether the job was done well or not.


  • Confident people are active listeners, allowing others to share and explore thoughts and ideas.
  • Cocky people tend to be the talkers that never let anyone else get a word in because they want to convince everyone of the value they say they bring.


  • Confident people relish achievement and enjoy contributing their talents and insights to the world. They don’t feel threatened by others’ successes or ideas but instead try to learn from them.
  • Cocky people need to believe that they are on top even if reality says otherwise. This can lead to manipulative and callous behavior as they focus on defending their power base, no matter how ruthless.

Here are a few questions to ponder: Which side of this fine line do you fall on? Which side would you like to be on? Which type of person do you want to be on your team? Which kind of person do you believe will foster collaboration and innovation? 

Lesson #12: You get what you tolerate.

This lesson applies to just about every aspect of life and business. I believe this is why it’s crucial to set expectations.

For example, in my days of freelancing before Raine Digital, I had a client who was constantly pushing the boundaries. Every project seemed to creep out of scope, and every invoice was met with resistance and post-work cost negotiations. One night, this client called me at 11:45 pm. Why? Because they’d seen an email come in from me around 10:00 pm. What’s worse? I took the call. 

That late-night call involved the client having a full-on meltdown about the product launch that was already set in motion. They changed their mind. They wanted me to stop all the promotions, advertisements, social media posts, website updates, etc. They were slated to automatically begin at 8:00 am the following day. The reason? They got cold feet about putting themselves and their new product out there. That’s neither here nor there. The worst part is, they refused to pay for the after-hours work that occurred that night.

You better believe that situation set a whole new world of policies, procedures, and contracts into motion. Never again have I emailed a client after business hours. If I am working late, those emails get scheduled to send the following morning. My contracts very clearly lay out the terms and conditions and fee structure. Our work (most of it) requires non-refundable deposits or full payments upfront. 

The lesson is, no matter what you’re doing, you’ll be treated with the behavior you tolerate. This is why you have to set expectations clearly. You have to set boundaries. This principle is true in every aspect of life.

Lesson #13: Emotions are a gauge.

Emotions are not supposed to be suppressed and ignored. Emotions should not run your life. They are something to be monitored, sort of like a gauge.  

For this one, I think I have to share a story with you. 

I remember working a job several years ago that had me spread pretty thin. I had been working six and seven days a week for months. My downtime was never really mine. I was always on call. Much of this had been my fault, as I failed to set appropriate boundaries and hadn’t learned how to say no effectively. I remember going through my monthly planning, and I had a month that was fully booked. I mean, fully booked. 12 to 18 hour days, literally seven days per week. I wasn’t sleeping. I was always eating on the go. The guy I was trying to date (understandably) struggled with my lack of availability. My excuse of always working was interpreted as not being that interested. I was losing friends because I didn’t have free time. If I did and went out with a friend, our outing would often be interrupted with work. 

Eventually, after months of this, I hit my breaking point, and it wasn’t pretty. I went into my boss’s office and just lost it. To be honest, I was so exhausted and burnt out that I don’t even remember all the details (but I believe there were both tears and curse words all tangled up in that breakdown). My emotions, which I had buried very deeply, came out in an explosive, uncontrolled, and embarrassing way. 

My boss was shocked. He had no idea I felt the way I did. He had no idea I was working as much as I was. I was given a fair amount of autonomy in my job. He relied on me to communicate what I needed to get the job done effectively. 

Fortunately, my boss was able to see beyond the outburst. Rather than meeting my fit with an equal amount of anger and emotion, he met me with a calm, rational, caring response. He listened. He required me to take some time off, and when I came back, we talked about the state of things. 

We worked through lightening my workload, new hires, unproductive program cuts, and various other aspects of the job. But then we talked about me and my mental health. He said to me, “Lindsey, if you’re ever going to grow past this, you have to learn how to monitor your emotions. Your emotions are a gauge. You’re not supposed to let them run wild and control your life as many people do, but YOU, you’re also not supposed to bury them and ignore them. God gave us emotions for a reason. We’re made to enjoy the good emotions that result from good things in our lives, but we’re also made to take notice of negative emotions. When there’s a constant negative emotion towards something in your life, it means something needs to be addressed. It might need to be fixed. You are going to have to learn to pay attention to your emotions because if you don’t, it will cap you in life.”

The words that boss spoke will continue to live on in my head for the rest of my life.  I understand that there are people on both ends of the spectrum. Those that are driven to act by the slightest whim of emotion in the moment lacking discipline and the ability to consider the repercussions of their actions. Then there are people more like me, who can sometimes just turn off the feels to power through what needs to get done, until the pressure becomes too much and there’s an outburst that may require damage control. 

See, as an INTP on the Myers-Briggs Personality Type Indicator and an Enneagram 5 on the Enneagram Personality Test, emotions have not always been a strength of mine.  My emotions run incredibly deep, but my acknowledgment and expressions of them are sometimes clunky or sometimes a full-on struggle. 

Positive emotions are obviously easier for me to express, especially to those in my close circle. They may result in silly, loud, exuberant, or comical expressions or even the occasional child-like giggle. 

Negative emotions though, those are the real toughies. Sometimes it’s a fear of how they’ll be received. Many times my logic is at war with my emotion, deeming it as irrational resulting in an overwhelming and ongoing internal cycle of conflict until I acknowledge and address the emotion. I’ve become much better at this and those who know me best help me conquer that internal battle often. 

Studying human psychology and personalities is something I find fascinating. It helps me understand people, how they interact with each other, how they see the world differently. This study, in turn, helps me be a better person. It helps me be a better daughter, a better sister, a better friend, a better girlfriend, a better manager, a better leader, and a better boss. To get to this realization, though, I had to explore my own personality, strengths, and weaknesses alike. For me (especially a less mature and less educated me), I used to bury my emotions until I couldn’t anymore. They would come out as a life raft when things were overwhelming or too much. And as such, they typically came out explosively.

I’m not saying that I’ve mastered this quite yet (I told you–perpetual work in progress). However, I have learned to pay attention to emotions more. If I have a negative feeling towards something, I check myself. I ask myself why. If it’s with a client, I ask myself if something needs to be changed. Do I need to set more clear expectations? Do I need to have more clear communications? Are we having a misunderstanding? If it’s with a friend, perhaps I need to be open about something that bothers me about our friendship with the intention of resolving it. If it’s with my job, as it was in the story here, then perhaps it’s time for a change.

Disclaimer here, and it’s an important one, especially concerning relationships–I’m saying emotions are a gauge. They are a red flag that something needs to be checked out. Similar to how your check engine light comes on in your car, you need to take it to the shop to ensure nothing gets worse and fix whatever is broken. I encourage you to do the same with your emotions. When the red flag comes up, take the time to explore it. 

Just because you have a negative emotion towards something or someone does not mean the solution is removing it or them from your life. It means something needs attention. Something might need to be fixed. And sometimes (hopefully, rare times), you may have to separate yourself from that job, that situation, or even that toxic friend/relationship/client. My point is, I’m always an advocate for trying to fix something before burning it to the ground.

Lesson #14: Clarity is a game-changer, and it’s fostered through clear communication.

As Brene Brown talks about this in her book Dare To Lead, clear is kind; unclear is unkind. Feeding people half-truths to make them feel better (which is almost always about making ourselves feel more comfortable) is unkind. Mastery requires feedback. Honest, whole-truth feedback.

If you’re in any kind of leadership role, this lesson is so important. Too often, especially those that find confrontation difficult, we try to sugarcoat the truth to make people feel better. Doing this can create all kinds of confusion for the recipient of that feedback. I’m not saying you need to be harsh and insensitive in your delivery. But if you’ve got people working for you, working with you, and they’re not producing at the level you expect, you have to be honest with them–fully honest.

I’ve found that rather than just telling someone they missed the mark, if I walk them through how they missed it, and then, in turn, how they can fix it, the individual will be much more open to the feedback and often feel like they’ve grown through the process. 

This is one of the differences between a manager and a true leader. A manager alone will simply manage the situation, often with the least amount of effort and engagement. A leader is anyone who takes responsibility for finding the potential in people and processes and who has the courage to develop that potential. A leader will care for the individuals they work with. This style of leadership requires you to get in the boat with your people. It requires more of you, but the results are worth it.

Hopefully, this post will leave you feeling inspired. It is my desire that different parts of my lessons will resonate with each reader. Please don’t hold back any questions or feedback. I’d love to hear your thoughts! 

Drop me a message here or connect with me to get the conversation started!

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