Self-Employment: Three Things I Wish Someone Had Told Me

November 4, 2013   |   62 Comments

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The other day I received this text from a dear friend who had recently started her own business: “When you started your own thing, did you spend any time hiding under the covers?” Only the first three years, I replied.

There are particular inner difficulties in working for yourself. No matter how carefully your plan has been researched, how market-ready your idea is, how deep your faith, and even how much money you have, certain issues seem to arise. I began working for myself close to a decade ago and I’ve experienced them over and over. During this time, about 2 gazillion other people I know have started working for themselves and I’ve seen it in them too.

I applaud you, brothers and sisters! Please live your dreams. Please untether yourselves from the status quo. Know that you are extremely brave. And try to remember these three things.

1. Allow your daily schedule to arise over time and then have faith in it. When I first started working for myself, I tried to implement a schedule that mimicked as closely as possible the work I had just left (working for The Man in the entertainment industry). I sat down at my desk dining room table at 8a. I planned to “work” (on what??) as if I had a predetermined set of responsibilities. I broke for lunch at around 1. I planned to knock off around 6p.

I did it this way because I couldn’t imagine doing it any other way. Month after month, I forced myself to stick with this schedule because I thought that if I did not, I’d end up watching TV all day. Without a firm structure, I feared, I would not get anything done so I tried to replace the discipline of accountability to The Man with the discipline of…beating myself up.

It takes awhile to remove the harness of indentured servitude, so please be patient with yourself. Working on your own after years (or decades) of working for someone else often leaves an imprint of fear, lack of imagination, and self-judgment. Even if you revered your boss/company/mission, someone else has set the context and that “someone else” provided you with the safety and constraints of an other-referenced work setting. Thinking you can simply transfer that work ethic to your new situation is not only nutty, it is not good enough or big enough to serve your brilliance.

I tried to shoehorn myself into my old schedule for about 18 months when it dawned on me that I could do it another way. Instead of forcing myself to do this or that, I wondered, what would I do if left to my own devices? Would I watch TV all day? Would I sit at my desk, twirling a lock of hair and gazing into space? Would all my plans and dreams disappear into slothfulness?

Yes. On some days. But those days don’t trouble me as much as they used to.

This experiment was scary at first because I took away the net of predictability to find my own natural structure. I dropped what I was used to and also stopped listening to “experts” and their theories about productivity to see what my intuition told me to do. For some months, I experimented and it was from this that I learned to trust in my own crazy, circular, bumpy, odd process.

Here are the very loose parameters of the schedule that arose when I let my day unfold rather than hog-tie it to something external:

Do creative work in the morning, as early as possible. Try not to schedule anything, anything before noon. Safeguard this time. Even if I sit there twiddling my thumbs, sit there. Exercise before lunch. After lunch, do what takes the least amount of brain power. Towards the later afternoon, try to do some project planning. If I feel like working after dinner, I do. Sometimes I work on the weekends, sometimes I don’t.

This is what works for me, not you. You have to discover your own rhythms and this discovery comes only when you relax and allow your creative wisdom to guide you. It takes time. Throw in some good old-fashioned pragmatism and a couple of hard core reality checks and you’ll do fine.

Expect this to go fairly well about 30%-50% of the time. I know, that’s not a great percentage. But that’s how it is. Travel, loved ones, fatigue, and loss of heart can all interfere. That’s okay. It’s just you and you can figure out how to adapt.

This may always be a bit of a struggle but not because you lack discipline—because each day possesses so much possibility and so much richness that it is hard to figure out where to start.

2. Watch out for the roller coaster. The emotional ups and downs of working for yourself are extraordinary and have the power to dictate how you feel about your entire life. Someone sends you a positive email and you think, “This is working. I’m good at what I do!” Three people cancel their subscription to your newsletter and you think, “I’m such a fool, this will never work. People hate me.” You see a news headline predicting growth for your industry and you’re all, “It’s a sign! I’m on the right track.” You log on to Facebook and see someone doing exactly what you do but making beaucoups of cash and you fall into despair. “I’m such a fool, this will never work. People hate me.” Seriously.

It seems you are only as good as your last email or phone call. Don’t worry about it. These thoughts are only meaningful if you believe them. So when despair dawns (for the zillionth time), try to say something like this to yourself: “Oh, there’s that thing again that is pointing out to me how deeply I long for success in fulfilling my mission. I long for it so much that I’m incredibly sensitive. But every other time I’ve had such thoughts, they’ve eventually gone away. I’m going to assume that this current batch will too.” And when great hope arises, try for a mindset akin to this: “Things look awesome and I’m so excited.” Yay Cheering Back Slapping Celebrating Jumping Up and Down Congratulating Self for about 60 seconds. Then go back to work and enjoy how much you love the added energy that comes from faith in yourself.

PS If you have a book for sale on Amazon, never read your reviews. EVER.

3. Get away from your desk. I can be having the most down-in-the dumps kind of day and then go for lunch with a friend whereupon I return to work vastly energized. Even if you don’t talk about work, taking time away from your (necessary, useful) focus on yourself creates perspective. When you’re on your own, it’s very easy for that perspective to becomes twisted. I often say to my husband that my main job is managing my own moods. Connecting with others for a meal, a chat, a walk, a yoga class is more stabilizing than anything.

And of course, don’t be afraid to hide under the covers from time to time. We all do it. I might be doing it right now.

*Special thanks to Seth Godin for continual reminders and encouragement. If you’re making the leap to working for yourself, his books and daily newsletter are a must.

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62 Comments

  • Posted by:  Maia Duerr/Liberated Life Project

    Awesome-ness. Thank you, Susan.

    • Posted by:  susan

      You’re so welcome!

  • Posted by:  Angela

    YES. Thank you.

    I’d love for you to write more on this topic. You are right that a gazillion of us have gone to work for ourselves in the past decade….

    • Posted by:  susan

      It is such a strange ride. Happy to try to write more. Any particular aspects of interest to you?

      • Posted by:  Angela

        I left an academic career to start a yoga school in 2011. It was all pull factors – I was far more comfortable in the institutional environment of academia and the identity of an intellectual. But I loved yoga teaching too much, and finally (gratefully) I gave in to it.

        In these these first 3 years as a business owner, I have found it very helpful to trust that teachers get the students they deserve, and vice versa. This enables me to support the students I have with conviction, and also enables me to set boundaries when it comes to “the marketplace.” I don’t need to try to influence the market too much – the market will sort itself out.

        This is a hilarious coming from the mouth of an ex-economic sociologist (whose head is full of critiques of “the invisible hand.” But, there it is. I trust that the people I’m supposed to serve will find me, and I will find them. Without much effort.

        So, that’s my approach as a relative beginner.

        Susan, do you have a perspective on markets? On how you and students or readers find each other? Or on how to work with your own mind in this regard?

        • Posted by:  susan

          I loved reading this! And let me think on the market issue…am about to head out to a yoga class! Back at you soon. xo S

  • Posted by:  Amy VC

    Hello fellow Shambalian! I found out about you from Seth’s daily postings and now you both nourish my self-employed self. Another fantastic resource for those just beginning the self-employed ride, and for those who need reminders not to lose our minds, is Pam Slim. She has a great blog/newsletter and her book “Escape from Cubicle Nation” is a must-read. Practical and inspirational.

    Thanks for all you do, Susan!

    • Posted by:  susan

      So glad you mentioned Pam. She is wonderful and her work is practical and inspirational, just as you say. I’m looking forward to her new book, “Body of Work” is the title, I believe. Ki ki so so! Susan

  • Posted by:  Alex

    Thank you Susan!

    Nail on head indeed. I also find it helpful to trust time. Great success doesn’t happen overnight, and often our initial idea of great success doesn’t happen at all. But occasionally our ideas evolve into even better ideas and those eventually lead to something really important that maybe we weren’t ready for in the beginning. Tenacity is a magical thing. Hakuna Matata is also a great moto when I find myself hiding under the covers. Cheers!

    • Posted by:  susan

      Love this! Hakuna Matata it is. Warmly, S

  • Posted by:  Andrew

    People like to boil everything down to money – I guess because it is measurable – but what the last six years running my own business has shown me is that you also need time and energy. Meditation creates more of both.

    • Posted by:  susan

      Agreed on all counts. The energy bit is particularly important.

  • Posted by:  Ash Faith

    WOW.
    I was literally just pondering all those thoughts you listed above.

    Thank you soso much for posting this. Working for yourself & sharing writing seems to be such an unexpected obstacle I’m encountering. I can think of a few things that led to me shying away from sharing my writing, but they’re just excuses in the end. Excuses that can be re-Cognized with understanding & reformatted towards evolving–

    honoring process in present presence.

    Thanks again Susan.

    • Posted by:  susan

      “Honoring process in present presence.” I love that. Glad to be on the journey together, Ash.

  • Posted by:  Vegemitevix

    I’ve worked for myself for over 20 years in three different countries in both hemispheres and in all that time I have never read anything that says it so perfectly. Excellent. Vix x

    • Posted by:  susan

      Thank you!

  • Posted by:  Shelly Drymon

    Great advice and timely. Newly self-employed with two new jobs on my desk I appreciate the advice “Allows your daily schedule to rise over time and have faith in it.”

    The comfort of a regularly dictated schedule from the days of my desk job are now gone. And like you stated I find myself trying to mimic those days.

    Your advice noted and taken!

    Thanks!

    • Posted by:  susan

      Wishing you the best, Shelly.

  • Posted by:  Jennifer Brilliant

    thank you. I needed and love this.

    • Posted by:  susan

      xxoo, big hug, Jennifer.

  • Posted by:  Devra

    yeah, very good ideas.
    thanks for telling me
    🙂

    • Posted by:  susan

      Glad!

  • Posted by:  Fiona Redshaw

    Thank you Susan.

    I am going to keep this and re-read it and re-read it! Not (yet) being self-employed but at home studying my passion and doing some work-on-the-side towards self-employment, I can completely relate to all you say. You have a beautiful knack for putting what feel like confusing, complex and emotionally charged issues so succinctly into words with a magnificent human touch! Ahh…thank you so much xo

    • Posted by:  susan

      You are so very welcome, Fiona. And thank you for the kind words. xo S

  • Posted by:  Mykel Dixon

    And there it is.

    I’ve spent all of this year living in a geodesic dome I built on an isolated beach in Cambodia. My intention was to explore and experiment with my creative process to uncover my optimum working conditions so I could pump out quality content forever.

    All year I’ve been coming at it from what I thought I ‘should’ be doing. What ‘the man’ says I should be doing. Or what I thought ‘the man’ thought I should be doing. Rather than listening for and trusting my own intuition.

    This post just sings for me. I can’t thank you enough. It puts a years worth of work in perspective and has opened up a whole new vibe for me. Really thank you!!!

    I’m not even sure how I ended up here and I never comment on blogs but you got me! I’ll be sticking with you for a while yet! Brilliant stuff.

    • Posted by:  susan

      I am so thrilled to hear this, Mykel. It is so good to know you’re not alone, isn’t it?

      Your experiment sounds amazing–and very difficult in the sense that it is full of space. Once, when asked what our biggest fear was, Tibetan meditation master Chogyam Trungpa said, “space.” When you’re self-directed, that makes total sense!

  • Posted by:  Susannah Conway

    “My main job is managing my moods” — I’m hearing you on that, sister!

    • Posted by:  susan

      Right?!

  • Posted by:  sirena

    Can’t thank you enough for sharing this. Thought I was ungrateful or a little insane. Now i see its “normal”.

    • Posted by:  susan

      Glad!

  • Posted by:  Anne

    Love it! I recognise & sympathise & smile with every single sentence. Thanks.

    • Posted by:  susan

      Right?!

  • Posted by:  susan

    This is such a strong post. I’m going on my 19th year of self employment and all of it rings so true. Like everything, feelings of success or failure ebb and flow. One of the most difficult aspects of working for myself is not taking those ups and downs personally–not so easy to do when you’re a one-woman team. 😉

    • Posted by:  susan

      I relate…

  • Posted by:  Faith Presley

    Thank you for this encouraging post. It can be difficult to break away from old routines and ideas. Your encouragement is welcomed.

    • Posted by:  susan

      You are so welcome.

  • Posted by:  DrDC

    Self-employed for 18 months, and was slowly going crazy trying to stick to the “standard office schedule”. Your point #1 made so much sense to me, and made me realize that I’m not alone on this. I’m in technology, but the practice of quietly being creative has brought on new spaces for exploration in the business. Thanks so much!

    • Posted by:  susan

      You are so welcome. It is so freeing to realize there is another way.

  • Posted by:  Debbie

    Wow, I wish I had read this 3 years ago! So great of you to share Susan. Most people put on the happy face, and we can feel that we are the only ones struggling. I am finally learning to trust the unpredictability of working for myself, but still have days that are a challenge. Good to know that I am not the only one that wants to hide under the covers sometimes!

    • Posted by:  susan

      You are definitely not alone!

  • Posted by:  Mopsa

    Wow. I couldn’t relate more to what you wrote. I don’t have a business, but I’m working to finish my PhD thesis.
    With time, I also found my ‘natural’ schedule, and I also feel like it’s a lot about managing my own moods.
    It was great to read this 🙂

    • Posted by:  susan

      So glad to hear this.

  • Posted by:  Marian Knowles

    Thank you for this post. It’s so good to know that it’s not just me struggling with my internal critic. After reading this, I feel like I have “permission” to break from the past and not default to the corporate approach that worked pretty well in my previous career, but don’t serve me today.

    • Posted by:  susan

      Wonderful.

  • Posted by:  beachmama

    So it’s not just me?! People tell me their writing/painting schedules and I think to myself, “I am such a freeking loser . . .” Thanks for pointing out there is more than one way to skin . . . well, you know . . .thank you!

    • Posted by:  susan

      It’s definitely not just you!! There’s at least you and me… 😉

  • Posted by:  Ana Isabel

    Loved it! I could totally relate to it.

    Thanks for the honest cheer up talk!

    🙂

    • Posted by:  susan

      Definitely.

  • Posted by:  Kayla Dawn Thomas

    Thank you for this post! I got serious about my writing schedule when my daughter returned to school this fall, and am currently trying to alter my schedule and increase my hours. This post helped me to remember my natural rhythms and why I chose to work for myself. If don’t stay true to those things, it’s not going to work.

    • Posted by:  susan

      You are so welcome! Wishing you well.

  • Posted by:  Michelle

    I love this post. So very true not only if you work for yourself but if you work from home for someone else. I have a lot of flexibility in my schedule, but shifting to work from home had me feeling all of the things you mention above. I love the tips.

    • Posted by:  susan

      Glad!

  • Posted by:  Bruce Hopkins

    I am a brand-new reader. And a recovering Type A. As a small business owner with 15 employees I was making myself crazy with piles all over my office, lists of to-do lists, and an impulsive, idea-a-minute mind. A zen counselor advised throwing all the piles and lists in the trash and practicing doing what struck me when it struck me. But, I had to complete a next step in the project, big or small, before moving on. Her logic was that the things I thought of most often were the most important and would get the most single steps and therefore get done first. It worked beautifully for the last 10 years of my career. (I did also designate a solid employee to be the one to remind me when something urgently needed my attention.)

  • Posted by:  Eileen Burns

    Rule # 1 for me was….In the morning there is NO SUCH THING as laundry or a washing machine. There is only breakfast and the workroom….and whatever might be going on outside the windows of the workroom….There is NO PHONE, NO E-MAIL…..you know the drill. But washing the kitchen floor in the middle of the night is perfectly fine, because Georgia O’Keeffe once said that she’d do it to clear her mind…..!!! I guess the rule is…there are no rules.

    • Posted by:  susan

      Excellent rule…

  • Posted by:  Mo

    Might I dare….
    4. Sleep on it….. Breathe deeply, stay in the moment, and then exhale……One’s inner self keeps working to cleanse, calibrate and clarify….. All while we sleep. When one awakes, the horizon is met with a replenished self, able and open……..
    Ok….dared….

  • Posted by:  Lisa Harris

    Susan – I just saw this. Perfect and awesome for me now!

    Thank you!
    Lisa

  • Posted by:  Patrick Leclercq

    Thanks Susan,
    Your words remind me of the 2002-2004 discipline I compelled myself to in an attempt to be responsible of my own activity after what I felt was a cruel dismissal.
    I feel I am about to experience once more being made redundant in spite of the care I put and the success I get in the shrinking tasks I have been sidelined to. If this does not indeed constitute an unshakable asset, I have however 5 years of ingrained daily discipline of noticeably stabilizing meditative practice. (managing my own moods is also my main and by far my most rewarding job). Similarly as you mentioned in the relational domain, I might well soon feel a truly devastating “heartbroken experience” (33 rd job and as much moves across France to make a living which, thank God, makes more and more sense)
    As Jon Kabbat-Zinn very roughly told at a recent Wisdom 2.0 talk : We really should first take care of our way of “being” before considering engaging in some new service to the human community (“doing” a new stuff).
    But who knows, my dark thoughts might be wrong, and the next interview with my two managers might turn positive ? But, to prepare this interview, as JKZ concluded one of his retreat : You really want a mantra ? OK, here is one : “Just fucking do it” (meditate). I hope I’ll stick to that whatever happens : “Meditation is nothing less than preparation to your own grand finale” (Löpon Chandra Easton, Wed 22nd Feb 2017 at Against the Stream)
    Take care Susan

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