10 Lessons from 6 Months of Working Independently

It has been 6 months since I left my job at Macalester College as the Director of Campus Life to work on my own. It has been both wonderful and totally weird. I’ve given up stability for freedom. I’ve learned a great deal about myself through the transition. Here are some of those reflections so far.

1. Free from External Structure…Now What?

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Our family had been planning a trip to Hawaii for my in-laws 40th wedding anniversary for 5 years. Fortuitously, this 2 week trip to Hawaii came just after I ended my time at Macalester. The physical and cultural distance of Hawaii helped me to completely disconnect from my job, role, and lifestyle at Macalester. Without the benefit of that trip, I likely would have continued doing what I had been doing at Macalester; I just would have been doing it from home. We all want to be free from externally imposed structure on our lives. Once I was free from that external structure, I needed to figure out what structure I would create to replace that. There aren’t a lot of alternative models out there. I am still figuring that out.

2. I Still Have a Boss


Although I work for myself now, I still have a boss – me. I’ve realized what a luxury it was to be able to externalize my frustrations about deadlines, projects, tough decisions, political realities, and more. Tough decisions still need to get made. I just have to make them. When I need to put in some extra time on a weekend, I have no one to blame or be annoyed with other than myself. When I need to take on a project that I have less enthusiasm for, it is me that has to tell me to buckle down and suck it up. Don’t worry about me and my new boss. We’re actively working on our relationship.

3. Productively Distracted


A friend who has been doing freelance work for about 10 years shared this concept with me. Productively distracted happens when you are spending your time on a totally justifiable distraction. For example, you see an article about anti-racism posted on Facebook and check it out. From there you find three links to other great stuff you’ve never read before so you open those tabs too. Next thing you know you have spent 90 minutes being productively distracted. I don’t waste my time watching cat videos, but I am the Jedi Master of being productively distracted. Facebook and Twitter are my enablers at being productively distracted.

4. Quality Output Over Time on Task


I’m a pretty disciplined person. Previously my discipline has been directed to being on task. I would focus my energy to sit down and really grind it out. I’ve learned that this isn’t always a good idea. For example, I recently was working on a grant proposal that had a 400 word (2 paragraphs) question. I spent 2 hours working on this one day and then another 2 hours the next day. My answer was still terrible. I finally gave up and went for a walk. I got 3 blocks from my house and had the whole thing figured out in my brain. I went home and typed up that good thinking in 5 minutes. My goal each day is to produce the best quality and quantity of output I can. My challenge is to figure out how to structure my day so that it leads to the best writing, coaching, presentations, research, proposals, connecting with clients, social media, and more. Some times a walk, workout, or even a nap could be the best thing I can do to help me to do my best work.

5. Sharpen the Saw

This is Steven Covey’s 7th habit of highly effective people. You’ve got to perfect your instrument. If you invest the time in sharpening your saw that you can actually save time overall as you cut down the tree. My instrument is me. I find that I am totally capable of grinding it out, which doesn’t always payoff. On the other hand, when I take time to really take care of myself, that time invested is always returned to me with clearer thinking, better priorities, and more quality output. For me, sharpening the saw includes getting enough sleep, meditating each morning, exercise, eating well, drinking lots of water, 26 minute nap, avoiding distraction, and making time to learn.

6. Productive Over Busy

When you work for someone else and get paid a salary, you generally would like to be as un-busy as possible. When you work for yourself and need to generate income, you want to be as productive as possible without being needlessly busy. There is a delicate balance between having a full schedule that keeps you productive and earning to meet your financial responsibilities and too busy with more work and commitments than you have time to meet.

7. Essentialism


I’m a big believer in setting priorities. Working for myself means that I get to set priorities based on my values. There is no shortage of pulls on my time, sometimes even more “to do” than when I had a full-time plus job. I can’t do it all. So I need to invest time in figuring out what will have the greatest return on my investment. The book Essentialism outlines the value in doing this and is one of the best books I’ve read in the past year.

8. Other People’s Reactions

Most people respond to my transition to working on my own with the same phrase, “Good for you!” but with totally different meaning. I regularly get a wistful “Good for you!” followed by an explanation about how they always wanted to do that and how great it is that I am take the risk. I also get a resentful, “Good for you!” through gritted teeth and walking away with the hidden subtext being “What the hell makes you so special?”

9. More Presence


I’ve been very surprised at how much more present I am able to be in my life. I thought I was pretty present previously, but I had no idea. I no longer live for the end of the semester, the next break, end of training season, or summer. I also don’t live for the weekend and the end of the week or for 4:30 and the end of the work day. I usually want each week and day to last just a bit longer so I can get a little bit more in. My weeks and days are full with a variety of different work that I am generally fully invested in. I enjoy what each one offers and am not surviving just to get through it. I’m more fully present and able to focus on the uniqueness of each week, month, and season. I’m also much more present and patient as a partner and a parent. Not only does this allow me to be a better parent but I also enjoy it a great deal more. This mindfulness means I am able to appreciate each stage rather than just hoping that we move on to the next stage more quickly.

10. Being Alone Is Not Necessarily Lonely

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I’m alone much more than I ever have been, but I’m generally not nearly as lonely. Being around others and not having the kind of connection we feel we should have is lonely. It’s been great to connect with colleagues via technology (Facebook, Twitter, LinkedIn, Skype, and Google Hangouts) and building relationships with new collaborators and clients. Deepening and expanding my relationships, friends, and community in this way has been a real benefit.

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