The Reality of Self-Employment

Growing up, my dad was an entrepreneur. He built several businesses, starting from scratch again and again without hesitation. His cycle was to climb a ladder, only to jump right off, and climb up all over again. Once I asked him why he didn’t get to the top of the ladder and just relax there for awhile… he said, “Because I don’t climb to get to the top – I climb to feel the resistance.” In other words, it’s the feeling of the climb itself, the challenge, effort and reward in doing something hard with nothing propelling you forward but yourself, that he was after.


As a kid, his career path seemed so brave to me. The thought of putting myself out there in that way, stating, “THIS IS WHAT I’M DOING” made me want to crawl under a rock. There was something that seemed so impossibly exposed with trying to succeed publicly like that. Although my dad is known to worry just a tad, I think his overall attitude toward life is, “What’s the worst that can happen?” It seems that has given him the freedom to turn his ideas into realities. Some of that must have rubbed off on me because here I am following in his footsteps as an entrepreneur.

How did the shift happen? It certainly didn’t happen overnight, but I think the fear of not trying to create the business I dreamt of eventually became scarier than just doing it. I also shifted my definition of success from “Success = X Result” to, “Success = Just Going For It.”

By taking the leap, I now know what he meant about the ‘ladder’s resistance.’ I like making it up as I go, having full control over my time, and feeling creative on a daily basis. That said, working for myself isn’t all ‘sunshine and rainbows’ or ‘days off and dollar signs’ – there are real challenges that come along with it. Despite having an entrepreneurial father and marrying someone who is self-employed, I didn’t really understand the challenges until I was the one experiencing them.

Top 3 Self-Employment Challenges I Experience:

1. Drowning in ‘time freedom’

I know this problem might come across kind of like “Wahhh, my diamond shoes are too tight,” but the struggle is real. When no structure is imposed, how do I really know how to spend my time?

2. No sense of when enough is “enough” 

It’s difficult to know when I’ve done enough in the course of a day, and even harder to know how and when I can give myself permission to be “off the clock” and relax.

3. Being a ‘shell-less’ lobster 

I recently learned that lobsters need to shed their shells when they get too big for the one they are in, and for a period of time, they seem “shell-less,” exposed and vulnerable. This is how I would describe the leap to self-employment, just wandering around the ocean-floor, gradually growing a new harder, thicker shell.


In response to these challenges, I’ve experimented with several systems, routines and strategies. Below are the ones that have proven most effective so far and are the basis of the coaching work I do with fellow self-employed artists, entrepreneurs, and those who manage their own time.

Top 5 Self-Employment Strategies I’ve Learned So Far…

1. Get Crystal Clear

I was asked the following questions a few years ago and they were game-changers for me…

If you had no worries about money, how would you spend your time? What would propel  you to get out of bed in the morning? Describe your ideal life in excruciatingly clear detail (what would you be wearing, what would you eat, where would you be, who would you be with, how would your hours be spent?) How much would this ideal life cost?

For me, the answer was wayyy less $ than I’d expected, given my main joys in life are pancakes, reading, trying to be genuinely helpful to others, learning, exercising, traveling, making homemade food, and laughing at jokes told by my family members (despite my husband’s belief that I’m overly generous with the term “hilarious”). I also realized I LOVE being productive and useful, so even if I had all the money in the world, I would still seek opportunities to try to help others. This exercise helped me get clear on what kind of business I wanted to create, why, and what its goals and measures of success would be. This clarity of purpose has become my roadmap.

2. Keep a Macro To Do List

I use OneNote. I love it because it’s free, syncs my laptop and phone, and is organized like a binder with dividers and separate pages. It holds all the little things that clutter up my brain (i.e. work tasks, ideas, errands, birthdays, book lists, etc.). It’s a comprehensive place to store absolutely everything so my brain doesn’t have to.  Some people think a macro list like this will make them feel overwhelmed, but generally, the opposite is true. By externalizing the tasks to a list, it reduces mental clutter and the “overwhelm” of trying to keep it all at the forefront of your mind. I do this by sorting all my tasks into “buckets” (or categories) and choose a handful to tackle each week. If I’m in the middle of a task but something pops up that I need to remember or act on later, I simply drop it into OneNote – that way my brain knows I won’t forget, and can go back to the task at hand.

3. Some Structure = More Freedom 

This is counterintuitive for most of us, but I’ve found putting some structure into my days makes me feel much more free. I decide at the start of each week what needs to happen. Then using my long-term goals and ‘Macro To Do’ list to guide me, I create clear priorities for the week. After that, I assign those “must-do’s” to specific days. My goal is to feel free yet productive, room for inspiration while also strategically working towards my long-term goals at a healthy, sustainable pace. Each day has priorities identified and answers the following question:

Ex: “Today is successful if these things happen… “

  • Coaching session with Lisa
  • Coaching session with Mark
  • Finish/post blog
  • Send contract to Beth
  • Yoga class
  • Drop off dry cleaning

With these decisions made, I have complete freedom to figure how and when to complete the tasks for the day, giving me a huge sense of accomplishment, increased productivity, and more focus while working. Plus, my “free time” feels earned, and can be enjoyed without stress or guilt.

4. Make Your Time Visible

It’s hard to set realistic daily expectations for ourselves. We tend to overestimate what we can accomplish in a day or week (and underestimate what we can accomplish in a year). Many people struggle with ‘to do’ lists because they expect to be able to do more than what’s realistic in the course of a day, and end up feeling defeated or that they’ve failed when they eventually fall short of their expectations. To combat this, I’ve found it helpful to write out my plan for the day, in order, with times associated. This makes it difficult to get overly ambitious, and instead, helps me to stay realistic with the time I actually have available (so my “daily priorities” can be aligned with my true capacity). The goal is to get as accurate as possible (by accounting for all the “extras” we do throughout the day, giving ourselves buffer time for the unexpected, and also giving ourself breaks so it doesn’t feel like a sprint). Accuracy takes time, so don’t be discouraged if you are only 50% accurate at first –  just try to improve day by day.

Example: Daily Plan

  • Wake up (7:30am)
  • Breakfast, read, meditation (7:45-9am)
  • Quick email check (9-9:15am)
  • Shower, get ready (9:15-10am)
  • Writing block – finish blog post (10-11am)
  • Coaching Call with Lisa (11-12:30pm)
  • Lunch break and check for urgent emails (12:30-2pm)
  • Coaching Call with Mark (2-3:30pm)
  • Break (3:30-4pm)
  • Send contract to Beth, *Order dishwasher tablets! (4-5pm)
  • Get ready/travel to yoga, drop off dry cleaning (5-6:15pm)
  • Yoga (6:15-7:30pm)
  • Dinner and relax!

5. Foster a Bias Toward Action

With tasks that are challenging or unclear, I’ve found waiting until I “feel like” acting doesn’t work. (Plus the energy it takes to avoid tasks ends up being more exhausting and anxiety-producing than just going ahead and getting started). I’ve found it more helpful to ask myself, “What is the smallest possible action I can take?” Then, I do that and reward myself for it. We tend to avoid projects and tasks that feel tangled or muddy in our minds, and/or are extremely large undertakings.  Try not to think about ‘everything that eventually needs to get done’ because if you do, your small action will seem insignificant and you may get overwhelmed and talk yourself out of doing anything at all. Instead, trust that taking ANY small action will make you feel better and lead to momentum over time. Starting a new task requires “activation energy”, which is a much bigger “energy withdrawal” than the energy you need to continue a task. I try to use this knowledge to my advantage and take baby steps until the pathway becomes more clear. Many things I need to do feel daunting and are not yet “figured out,” so in the moment, I definitely don’t “want” to act – but once I take ANY action, I feel more inspired and motivated to stay in it, and the solution or pathway inevitably reveals itself.


With self-employment there can be uncertainty, lack of stability, an ongoing ‘hustle,’ and yes, you’ll wake up some mornings asking yourself, “What the heck am I doing?” But I don’t think any job is without discomfort or unpleasant aspects. The truth is, we can choose what we are willing to ‘suffer’ for. Not all aspects of running my own business are easy or fun, but I genuinely like the problems I have now, and that makes all the difference.

(If you are interested in learning more about 1:1 coaching with me, click here.)

Thanks for reading!


2 thoughts on “The Reality of Self-Employment

  1. I LOVED this post. Thanks so much for giving a real glimpse of the entrepreneurs ‘day to day’ Kailea.
    I really loved seeing your map of a day, because it really made me feel less alone in how I lay out my day as a self-employed musician.

    I love the ‘quick check’ of emails in the morning. That was a big ‘aha’ for me. I tend to leave checking email until the afternoon, but by that time, I really only have a couple of hours to reach people, which makes me a bit stressed. I’m going to incorporate that into my day.

    Here’s how my day typically looks. I finally have a solid healthy routine in place for my mornings, but tend to just “WORK” from 1pm to 8pm. I don’t like it, and I’m going to try and put some structure into there. Any tips?

    Meg’s Day:
    8:30 am Wake up, brush teeth and set a pot of coffee
    9:00 am Meditate for 15-20 minutes
    9:30am Get coffee and read a good book on the ‘comfy chair’
    10:00am Creative music time (play around on the guitar/songwriting)
    11:30am Prep lunch and listen to podcast
    12:00am Go into office space (I really don’t like the ‘vibe’ of an office, and work better in a library. So I actually have to force myself into my office every day now that we live in the country).
    1:00pm-5pm wildly answering emails and laying out plans for 2018/2019.
    5:30pm Make supper while watching Bob’s Burger’s/MADMEN
    6:30-8pm Stress that I didn’t get enough done during the day haha.


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