7 lessons learned in two years of self employment


As of this month, I’ve been working for myself for TWO WHOLE YEARS.

(Queue all the cliche things coming out of my mouth: where did the time go? I can’t believe it! It doesn’t feel like that long! etc. etc.)

The last two years have also, incidentally, been two of the most tumultuous years of my life. I’ve weathered the passing of family members, worried over loved ones in the hospital, experienced massive anxiety in myself and the people around me, along with entirely new levels of personal challenges that are, apparently, unavoidable and inevitable symptoms of being human (I know that for sure. I tried really hard to avoid all of them).

Today, for your reading pleasure, I will share some of the things I’ve learned from being my own boss.

Lessons learned in 2 years of self employment

1. I’m not a perfectionist….but I am a control freak.

When you leave the stability and structure of a day job, you uncover a world of uncertainty that will test you to your core. I hesitate to even say I’ve gotten better at accepting uncertainty, even though I like to imagine I surely must have, right? But I’ve truly become aware of how much uncertainty there is in simply being a human on this planet. And that my own inclination is to try to control it all.

God grant me the serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference.

2. The thing that works right now doesn’t have to work forever.

I mentioned this idea in a post about treating everyone like a toddler, back when I was freshly struggling with trying to find a new routine in the absence of my old structure of life that was provided by my job. The lesson has come up over and over and over again in the last two years…there’s no such thing as normal. There really never was. Life is a series of experiments, and if you find a tool or a tactic or a mindset that serves you well, embrace it. And if it doesn’t work two weeks from now, you get to tweak it or  let it go to adjust to a new set of circumstances and needs. This is true in business, in relationships, in keeping your house clean, in habits and in health, and it makes me more passionately devoted to creating flexible systems for home and work, that can keep up with what life throws at me (and you).

3. You get to teach people how to treat you…and it’s extraordinarily effective.

One of the chronic sources of stress at my day job was constantly being asked to handle “urgent” emails, put out fires and accommodate deadlines for projects that needed to be done yesterday…but I just found out about it today.

For a while, I thought that was just part of being in business. But since working for myself, I’ve learned that actually, I can create (and have created) a business with very few “urgent” scenarios to deal with. This lesson—and how I arrived at it— could be a blog post all on its own, but I will sum up to say:

Clear, loving boundaries are MY FAVORITE.

4. The journey from day job to dream job is more internal than external.

Before I started this journey, I thought I was just changing jobs. In reality, I was changing the way my insides worked—the thoughts in my mind, my attitude, my perspective, my beliefs about myself and how I fit in to the world. It became quite mind-blowing, actually. My journey toward being my own boss has actually unraveled a lot of patterns and internalized beliefs that weren’t serving me anymore, to uncover a more pure version of what is actually true for me, and my life.

I can’t tell which is the cause and which is the delightful side effect—the new career or the new, more authentic self I’ve become in order to achieve it.

5. Patience is a virtue.

This is a lesson I’ve seen in play both in my own journey and with the clients I work with who are building their businesses and working towards their own ideal career in self-employment. You start with a dream, but you don’t get to see it actualized immediately. The part between now and the hazy, dreamy “then” is a practice in patience. There’s no wishing away this phase of the journey. As much as you want to “arrive” at the end, there’s truly no way to rush your vision, or the time it takes for your path to make itself clear. (And, actually, in the end, that’s exactly as it should be.)

I’m not so great at patience most of the time. Which leads to my next lesson.

6. Frustration with where you are can be fuel to where you want to go.

About six months before I quit my job, I experienced a really frustrating disappointment. After a series of stressful months, I had an opportunity to work for someone with a sizeable freelance contract, which would financially allow me to quit my job immediately and have the time to start really building my business.

The opportunity fell through. I would have to stay put for longer. I felt a familiar rush of anger, resentment and frustration at facing a reality I no longer wanted—but this time, I channeled the energy and anger into a useful activity. I swore I’d never be caught unprepared again, and set to work making a website to promote my freelance marketing services. I couldn’t make it live to the world yet, but I could design it and write all the words and get everything ready. Because another opportunity WOULD come up.

To this day, that action marks the moment when my vision of self-employment truly became an inevitable reality. The day I left my day job, I made that website live. And in the six months leading up to that day, I knew my new job and new reality was just a click away, as soon as the right opportunity arose.

7. Everything changes when you keep promises to yourself.

This might be the lesson/accomplishment I’m most proud of over the last two years. More accurately, this lesson started about five years ago, when I realized I wanted a different life for myself than the one I was living, which felt like auto-pilot, and accepting the hand I was given. I wanted a life that was intentional and fulfilling and a dream, in essence, of living exactly how I chose. The progress I’ve made toward making this dream a reality can be attributed to developing the skill of first knowing what I wanted, and taking the action necessary to make it happen.

Maybe it’s not quite as easy as I’m making it sound…but I’m pretty sure it actually is that simple. And once you get good at it…things really start to get dreamy.


These lessons are nowhere near all the things I’ve learned about self-employment. In fact, I could probably fill a book with the lessons I’ve learned only thus far, and I’m quite sure I’ve forgotten some really important ones. But there you have it, friends. A snapshot of my journey.

Over to you—what resonates with you from the lessons I mentioned here? Have you come across similar ones on your own journey? Leave a note in the comments below!

// Photo via Unsplash