9 Steps to Self-Employment Success

Friday was my last day at the office. I had a final meeting with a colleague, put my last “out of office” message on my work email, uploaded my last post to the company blog, and packed up my personal items to take home. After fourteen years on various payrolls, I’ve set out to return to the life of my early twenties, full-time freelance writing.

The reasons for this leap off a cliff are many and varied. The final kick for me was motivation from the inspirational creatives I interviewed this summer on my cross-country road trip across America. But like many creatives who are driven by a bit of self-deluding mania, I believe I can actually make a go of supporting me and my family by putting my right brain into hyperdrive. I need to at least give it a shot.

The left side of my brain will have to work neuron-in-neuron with the right for this to succeed, however. So I’ve created 9 practical steps to success I intend to follow going forward. I invite in the comments section below thoughts on the wisdom and merits of these steps, and also other suggestions and observations.

  1. Set Reasonable Expectations: I could sit around and wait for a Random House editor to read this post announcing my self-employment and ring my doorbell with a seven-figure, multi-book contract in hand. Or I could beat the bushes for actual paying work that might not be high in prestige but would put food on the table. Over time I hope to be a bit choosy, but work is work. Brian Fitzgerald, the photographer I interviewed in Portland, Maine, has thrived in self-employment by taking occasional work that might seem mundane and bringing his creativity full-force to the project to make it less so.
  2. Follow a Schedule: In theory my days will be wide open. In practice I will be needing to write, to market, to handle back-office business matters. I’ll have periods where I’m highly creative and times where I’ll be lucky to be able to alphabetize my file cabinet. To stay disciplined and productive, I’ll need to create a schedule that maximizes my efficiency and then hold myself to it.
  3. Stay Connected: It will be easy to hole myself away in my basement home office, writing and dreaming. That won’t do professionally. I’ll need to get out of the house. I can go to professional gatherings. I can schedule lunch or coffee with former colleagues who I should really stay in touch with. Serendipitous professional opportunities won’t find me if I’m not easily found.
  4. Embrace the Interwebs: I have long been resistant to social media. I launched my Twitter account and this blog only a few months ago. I’m still not on Facebook. I remain in learning mode as far as how to grow from the connections I’m making online. I see little utility in turning my Twitter account into a recurring plea for work, but social media can be an extension of #3 above, staying connected and waiting to see what the universe manifests from that connection.
  5. Self-Promote: I have experience in marketing and communications, but I’ve generally promoted other individuals and organizations, not me as a self-employed creative. But done in a tasteful and considerate way, it only makes sense to let people know what I’m capable of offering them professionally.
  6. Keep Up the Business Side: This is something else Brian Fitzgerald talked about. Self-employed creatives need to do the things they hate, like calculating quarterly tax payments and keeping a ledger of expenses. They need to pay bills, send invoices, follow up with those who still haven’t paid for work. They need to send queries, and keep up their professional web site. I will do those things. And I’ll try to bring creativity to those tasks as well (but no “creative accounting”).
  7. Make Time for My Own Creativity: I knew I had to pursue self-employment when I realized I was giving all of my creative energy to my job. I loved my job and had no regrets about being “all in” with it, but my hope with this move is that at least some of the fuel in my creative tank can go into projects that may not have immediate yields. An analogy would be performing a bit of basic R&D in addition to project-specific R&D. Some of the most amazing inventions have come from scientists being free to tinker with no specific goal in mind.
  8. Embrace the Positive: I will face a lot of setbacks. Queries will go unanswered. Manuscripts will be rejected. To stay motivated, I’ll need to seize on the small victories and hold them tight.
  9. Show Gratitude: I can pursue this new adventure because I have a wife who is, while nervous, full of encouragement. I have two kids who know next Christmas might not have the volume of loot as the one we’re about to have but aren’t complaining. I need to remind myself of the support I’m receiving, and let those people know how much I appreciate their support.

We’ll see how the New Year progresses. I may find this summer that this list was completely misguided. But at least I have a plan, and I’m excited to move forward with it.

23 thoughts on “9 Steps to Self-Employment Success

  1. Patrick, you’re right on the money! Great steps. As a life/creativity coach you’d thinki i’d have it all figured out! Well HA! not. I have to have tricks to keep myself sane as an independent freelancer — coach thyself!!! My challenges are the rabbit trails i go down on a daily basis… i have to work to not get mired down by the details of the biz, and forget about the creativity that I love so much!

    So, here’s one of my tricks to make sure i don’t forget why i’m doing this! I use a bright yellow highlighter to color in Mondays in my daytimer. Monday us my creation day! I don’t do anything but create on Mondays. No appointments, no QuickBooks, No clients. Nothing but creativity, writing, journaling, whatever gets my juices going.
    The Yellow makes me happy when I see it. But if I don’t color it in in the calendar I forget and schedule stuff (works on Google calendar too!)…

    so, there, that’s my quirky trick. Onward, Patrick! You’re joining a great tribe!


  2. Kelly, thanks for the encouragement! I really like the idea of a creativity day, and making sure it’s marked down. You’ve also managed to turn the day most people find least enjoyable — Monday — into one that can be quite enjoyable!


  3. Congrats on embarking on your new freelance career!

    I’m really excited for you. From what I’ve seen on your blog so far, you have the makings for success. Not only with an abundance of creative material and creative thinking, but with your personality. You’re a “writer who’s good to work with.” That can mean just as much as writing skills, sometimes more.

    I love your list. I’ve been working from home for 10 years and I can testify that all nine points still apply. Here’s what I’d add in support of what you’ve already said:

    #1 – You probably know this already, but beware of getting trapped in low-paying writing gigs on the Internet. If you’d like to explore that topic as a cautionary measure, I can put you in touch with a friend who went down that rabbit hole and lived to tell the tale. Your plan to remain open to taking side jobs (I’m assuming you mean jobs unrelated to writing, such as temp work or unrelated freelance work) sounds practical.

    #2 – I agree, planning and scheduling is essential. I use a combination of Writer’s Digest Weekly Planner (highly recommended; great format) and Google Calendar to keep me on the path. I still get side-tracked (esp. by Twitter) but my lists and reminders help me get the critical stuff done on time.

    #4 – Embrace the Interwebs. Absolutely. I’ve offered work and other opportunities to writers I’ve met online. For example, several of my course presenters for the Fear of Writing Online Course were found by (a) reading another writer’s blog or (b) by meeting a writer on Twitter. All of these writers are also now good friends, so networking online is also precious when it comes to #3 – Stay Connected. It doesn’t all have to be business. Friendships with other writers keep me sane and fulfilled.

    #5 – Self-Promote. Here’s a Tweet I found reassuring, whether you’re selling a writing product or just yourself as a writer of interest:

    @trkravtin (Teresa Rolfe Kravtin)
    Some people are loath to “sell” anything. I understand. However, we all want to be “sold to” when it’s something we want.

    My biggest cheer squad hollers to you, Patrick, for a successful and happy life as a freelancer!

    ~ Milli


    1. Milli,

      Love your input as always, those are great points, and thanks for your kind words. I’ve heard some warnings about these Internet writing jobs. When I worked FT freelance in the early 90s there was no such thing, but I did get trapped by some unscrupulous folks in ripoff jobs when I first started. The scoundrels go wherever the suckers are, I guess.



  4. Congratulations on once again taking the leap, Patrick, you’ll do great. I love what you said in #1, about occasionally taking on a lesser job and bringing the full force of your creativity to bear on it. That’s a wonderful way to look at it. I got stuck with some low-paying jobs when I started out but following that theory I was able to turn them into great experience and move on up the rung.


  5. Congratulations Patrick on your brave move to living a life you want to live. You’ve got a good handle on what it takes to succeed. I’d add: do at least 5 new things and 5 follow up things each day, 5 days a week that will lead you to making money. They may be small, like a phone call, but the combination of persistence and consistency will get you where you want to be. It’s a great time for people who love to write -I look forward to following your “wins.” And those include great times with your family and doing the things you love, as well as bringing in plenty of money!


    1. What a great tip, Ann. I hadn’t really thought to quantify it like that, but it’s a way to know that I’m proactive every day, and if I write them down beforehand, I’ll get the satisfaction of crossing them off! 🙂


  6. Congratulations, Patrick, on taking the leap! I wish you the absolute best.

    I still have a part-time day job, but I can say from 3 years of self-employment on the side that your list definitely covers the basics. I really like the way you included embracing the positive and showing gratitude. Those are huge for keeping morale up and momentum going, and they make you more attractive to potential clients as well.

    The hardest part for me has been staying focused on what’s important. That’s really an ongoing practice and much like a muscle that needs a regular workout. 🙂 It’s worth the investment of time to get very clear on what is the best use of your time. I have it written out and posted so I don’t get led astray by the 100,000 distractions out there.

    Looking forward to hearing how it’s going!


    1. Sue, thanks for the encouragement and for your wisdom. My mind has been working overtime, telling me all of these writing and income avenues it wants to pursue, so my focus now is on the scheduling and the task prioritization. It should be a fun New Year!


  7. Patrick, I, too, want to wish you the best on your new journey. I think one of the hardest things to do when you embark on a life of self-employment is keeping a schedule. It’s really easy to slip out of it, make excuses or put things off that you initially set out to do on a regular basis, as well as achieve longer-term goals. Sometimes the balance between the creative interests you want to pursue and the business you need to keep going can shift. I’ve gone through periods where the phone wouldn’t stop ringing with job offers for great assignments and it was during those phases that I’d lament not having enough time to myself. The reverse would happen, too.

    You’re lucky to have a supportive spouse and understanding kids. I think you’re going to be alright. And I look forward to finding out more of what you do.

    Happy Holidays and best wishes for the new year. cheers, mari


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  9. Mari, thanks for your thoughts. As I just mentioned to Sue, the schedule is where I’m really focusing now, making sure I have one that maximizes my efficiency and is easy for me to monitor. Of course, I am also telling myself to stay flexible, because from week to week, day to day, hour to hour, I might need to change things up.

    The good news for me is that after a decade of short-deadline journalism writing, the last six years professionally I’ve had much longer deadlines on larger projects. Project management doesn’t come naturally to me but I’ve got some skill sets there that will be helpful that I didn’t have when I first left FT journalism. We’ll see!


  10. Patrick,
    I’m so glad to have found you as you start this new phase. I started with the same big bang just this time last year. I love your ideas and those of your readers as well. Best of luck with this.


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