The Best 4 Lessons I Ever Learned From My Boss

Truth time: I’m not good at social media. Not in the go viral and connect with thousands of strangers on the internet kind of way. I’m halfway decent at scouring Mombook or LinkedIn feeds, seeing something interesting happening in the life of an acquaintance I’ve lost touch with, and commenting something like: “Miss you! It’s been forever. We should grab lunch/dinner/schedule a phone call.”

Recently, a former boss of mine commented on one of my LinkedIn posts, and I suggested we have lunch. It was lovely to catch up after six or seven years. He was my first boss at my first full time job, where he made a significant impact on my career and my work habits going forward. I’ll always be grateful for the support he showed me in some truly wacky circumstances. Nonprofits can be wild, ya’ll.

As I drove back to my workspace after lunch, I reflected on various lessons I’d learned from the handful of bosses I had through the years. I strongly believe that managers have a major impact on quality of life in a workplace, but there’s lessons to be learned from both good and bad bosses – and all those bosses that fall somewhere in between.

I also realized that I no longer have a boss, and aspire to never have one again. But I’m not sure I’d have had the skills or the courage to strike out on my own and succeed at supporting myself without the lessons learned from the men and women who managed me throughout my more traditional careers. Here are a few lessons that resonated.

Don’t Let Email Control Your Day

I’ve written before about the importance of discipline and habits. People often compliment me on my self-discipline and desire to focus rather than multitask. I may be overselling myself a bit. Rest assured that I can and sometimes do procrastinate like the best of us.

But I did learn a lesson quite early in my first full-time job that has stuck with me ever since. And that lesson has helped me prioritize my workload and focus on tasks that are actually important instead of whoever’s screaming the loudest.

I do not let email control my day. That’s since expanded to texts and social notifications as well.

Both of my previous careers were very email-intensive. I had volunteers, and later customers, who needed answers from me, and they wanted them before they’d even sent the email.

Eager to please, I’d start my day as most professionals do, by opening my inbox and diving in. Before I knew it, it was quitting time and I’d answered a lot of emails and done little else. To add salt to the wound, my inbox probably wasn’t even empty.

Sean Covey calls that “the whirlwind.”

For months I lived in the whirlwind. I was providing pretty excellent customer service, I thought, by getting back to folks quickly. But I was not doing great at achieving the goals my boss and I had set together. You know, the income goals that would actually fund the programs that moved our mission forward. Because I was not spending any time deliberately trying to achieve those goals.

My boss asked me what was happening. So I explained about the inbox and the emails and everything the volunteers needed and how I just couldn’t get ahead of it, and there was no time for anything else.

I will never forget what he said to me.

“Is email really the most important part of you job?”

Well, no. But keeping my volunteers happy was. So, yes! I wanted to scream. Yes! Yes! Yes!

The correct answer, of course, was no.

With a few rare exceptions – my second job in customer care/inside sales perhaps being one of them – answering emails quickly is not THE MOST important part of a job. Even in that inside sales role, things like following up on large quotes or taking the time to actively go after big opportunities should have been more important than answering day to day requests, but rarely happened at all because we just drowned in our email for eight hours straight.

But email is so easy. It’s right there. You might get a little buzz every time you answer one and file it away. It’s like an automatically replenishing to-do list that provides Type A people with the chance to prove that they are SO BUSY and accomplishing SO MUCH.

Also, we now live in a society that expects instant gratification in every aspect of our life. So there’s even more pressure to drop everything and answer immediately, because that might legitimately be what’s expected.

The problem is, when you do that, you drop everything. And if you never have the time to pick it up, you will never do anything but what other people have decided is important.

If you want to take charge of your life, you have to take charge of how you spend your time and wrest back at least a little control.

My boss asked me to try an experiment. For the first hour of my day, I was not to open my inbox. I was to do something else on my to-do list that would be easier to accomplish without interruptions. I was, to use a word my writer’s group would consistently remind me about ten years late, to reclaim my agency.

I was skeptical. But it didn’t take long to realize my boss was right. During that email-free hour, I was getting stuff done. And I ended each day feeling less behind rather than more so. My volunteers survived. They didn’t even notice, until my email-free time stretched to two or three hours. By the time I left that job, I didn’t check email all morning whenever I could help it. And guess what: the sky didn’t fall. I warned my volunteers, explained why I wasn’t looking at email, and told them if something was urgent they should give me a call. I don’t remember anyone seriously complaining. Maybe because if what they needed was truly important, I was getting it to them before they asked.

After I unchained myself from my email, I hit goals more often then not. I created programs that incentivized goals for our volunteers. I had space to be creative and have fun while achieving what I was paid to achieve.

That was much more beneficial to myself, my volunteers, and the organization than if I responded to every email instantly (which I was not doing anyway!)

If you’re struggling to get something done, carve out some time every day to do it without distractions. I recommend first thing in the morning, before you open that inbox and get sucked in. Even if the rest of your day goes sideways, you can feel good that you accomplished something.

Perfectionism Isn’t Always an Asset

This lesson didn’t land at the time, but about a decade later I’ve come to accept that my boss was 100% right.

It was summer, and the whole region had traveled to a centrally located patch of wilderness for a staff picnic. To justify that we were going to spend some time during the work day socializing and were being reimbursed for mileage, we had to complete a workshop.

I don’t remember the point of the workshop, but I do remember we all had to answer this question: Perfectionism can hold you back, true or false?

My answer was immediate and unwavering. False. Being a perfectionist made me awesome at my job. I didn’t understand sloppy people who didn’t care when they made mistakes.

I was shocked when my boss stood up and declared that perfectionism wasn’t ideal. In fact, it was often a detriment and not an asset in the workplace.

I vehemently disagreed. Not to the whole group. But on the car ride home, as a few folks from my local office debriefed about our day. Perfectionism got you ahead, I swore. It didn’t hold you back.

About ten years later I’d listen to Craig Groeschel talk about the concept of GETMO – Good Enough to Move On. Just like my old boss, he asserted that if your top priority was being perfect, you reached a point where you were putting in a lot of extra effort for only a small amount of improvement. Truth be told, you might never act at all because you’re paralyzed by the fear that something couldn’t be shared until it was perfect. The trick was to recognized when something was good enough. At that point you had to do it and move on. Forward momentum was more important than perfection.

I’m not sure when I started to believe this. But sometime between that picnic and my first Global Leadership Summit, I lost most of my resistance to Craig’s idea, which was basically my boss’s idea just with a acronym and a productivity chart. I’m still proud of the quality of my work, and I flinch every time I notice a typo in a published book. (One day that will be my book, and I will learn to flinch and then let it go.) I still don’t know how to do something I know isn’t great. But I’ve accepted that perfect is a mirage and an excuse. There’s a bell curve on quality, and there’s a point where putting in more effort isn’t worth any minor improvement.

I’m imperfect, my work is imperfect, and that’s okay. It still contains a ton of value.

A lot of anxiety falls away when I’m able to embrace that.

I wish I’d listen to my boss sooner.

Self Care is Important (But Hard)

This was another instance where it took some time for me to really absorb something that in hindsight seems obvious.

I loved a lot of things about my nonprofit job. The mission, my volunteers, my coworkers. The type of work I was doing, and how good I was at it.

I did not love the schedule.

Working primarily with volunteers means you need to be available when they are available. And since most volunteers have full time jobs, that usually meant after 5PM, when your work day would otherwise be over.

All our team captain and committee meetings happened in the evenings, starting anywhere from 6 to 7 and usually lasting until around 9PM. Since I then had to pack up and drive up to 45 minutes home, I often didn’t get home until 10PM. This typically happened two, sometimes three times a week. Sometimes I also had weekend fundraisers to attend. In May and June, those fundraisers were typically 24 hours plus setup and cleanup time (i.e. at least 30 hours, maybe a few of which were spent passed out in a sleeping bag on the press box floor if my body was exhausted enough to shut down).

All this to say, it was not an 8 to 5 job.

I started this job relatively fresh out of a college that had been full of overachievers like me. After four years of conditioning to GO, GO, GO, I slid right into a job where there was endless work to be done and the stakes were literally life and death.

There was a sick sort of pride that I could probably trace back to high school – but definitely to college – in pushing myself more than one should be pushed. More work + less sleep = greatest potential achievement. Or so I thought. I know now that math is VERY flawed. (I was an English major anyway.)

Even though I was salaried and didn’t get paid more for working always, I had to track my hours. And the closer the number edged to 60, the more self-satisfied I felt. Sure, I was perpetually exhausted, my apartment was a disaster, and I had no social life whatsoever. But I was COMMITTED to my career.

My boss at the time scored frighteningly similar to me on a personality test we’d taken during another one of these regional “celebrations”/trainings, and it was very clear in his similar pattern of overworking.

So I was not expecting it when we were sitting down for an annual review and he told me he’d seen my hours, and he wanted me to work less.

Just like my knee-jerk reaction to being told email wasn’t everything, I thought my boss was talking crazy. How could I work fewer hours? There was so much work to do. But he insisted my health and wellbeing were more important than a few more hours on the clock. He even theorized that I’d be better while I was working if I worked less. Which science has actually proven, by the way. After 50 hours of work, productivity seriously declines.

But I was willing to go along with it – if my boss did too.

So began a very strange era when my boss and I held each other accountable for working less. We’d email each other every Friday to brag about how we’d done. My goal was to work fewer than 50 hours every week. Which was a significant improvement, even though technically I was only required to work 37.5 hours.

This was my first real experience dipping my toes into the waters of self-care. Now I absolutely shudder at the thought of working that much. After learning how much better it feels to work a reasonable number of hours and get a proper amount of sleep and not push my mind and body to its limits, I cannot fathom going back.

In most instances, it’s not necessary to be exhausted all the time – unless you have a new baby or a new puppy, in which case – hang in there until they grow up, I guess? But it’s certainly not an ideal to strive for. I absolutely hate the current focus on hustle culture. I get it, but I hate it. Working like a machine may be necessary for a time, especially if you’re starting a business or trying to launch a new endeavor, but when it becomes a lifestyle, that leads to a broken body, broken relationships, poor mental health, and crippling burnout.

Cutting my hours to 50 a week wasn’t drastic enough to save my nonprofit career. As much as I love helping people and want to make a difference in the world, I can’t fathom putting myself through working at a nonprofit again. Which is sad, but I’ve come to terms with it.

But I did learn an important lesson.

We’ve only got one body. Take care of it!

I Believe in You

I fell into my second career largely out of desperation. Burned out without a backup plan, a found a sales job at a manufacturing company through a few personal connections from that nonprofit job.

That company took a major chance on me. While I had acquired a ton of soft skills at college and my nonprofit job, my only real business experience was doing bookkeeping for my father and my post-college side-gig selling peafowl.

There was so much about that job that I enjoyed. It was a safe place to land as I learned that the work week was only supposed to be forty hours long and success shouldn’t always be viewed in terms of life or death. Everyone there tried their best, but I’d often hear people remark, “It’s only plastic” after – or during – a bad day. At my former job, no one had ever said, “It’s only cancer.”

I wasn’t emotionally invested to the same extent, which was what I needed at the time, but also probably what allowed me to leave for my third career chasing my true passion. But I did have a heart for making things better at my workplace. Cultivating teamwork, creating tools, improving systems. Helping both my colleagues and my customers. I worked with a lot of great people, and when it was time for me to announce I was leaving to finish my novel, I felt guilty about leaving them behind.

As I’ve shared before, I was terrified to tell my boss. Not because I thought he’d be upset, but because I thought I was letting him down. I felt like I was abandoning him and his entire team in the middle of a crisis. The supply chain was such a wreck, y’all, and we were right in the middle of it. And I didn’t think he’d see my departure coming.

I kept imagining how my boss would feel as a manager. I’d had volunteers quit unexpectedly on me when I was the one who’d have to replace them, and it was not a fun time.

But in the moment, my boss reacted as a person first, and I’ll forever be grateful for that.

“You’ll always be welcome back here,” he said, after I explained what I was leaving to do. “But I know you won’t come back, because you’re going to be successful.”

Top notch managing, right there. He could have very well made the conversation about how he, the team, and the company would be impacted, and he would have been justified. Instead he told me that he believed in me, and wished me the very best on my new journey.

That encouragement helped sustain me through the rest of my goodbyes, and bolstered me up as I built my new routine and later figured out how to run a business.

It’s so easy to get wrapped up in our own problems that we only see how circumstances affect us and not the others involved. I hope I never forget that people are individuals, not obstacles, even if our intentions don’t align.

A little encouragement can make a lasting impact.

A Good Manager Makes All the Difference

There we have it. Two companies, three bosses, and four important lessons that have shaped me into the worker – and person – I am today.

I’d love to hear the best lesson you ever learned from a boss. And if you are or have been a boss yourself, what lesson have you tried to impart on your team?

And if we haven’t seen each other in a while, shout at me in the comments or on social media. Chances are I’ll suggest we grab lunch.