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What I’ve Learned Going Into Business With Myself

April 9, 2012

I’ve been working for myself for four weeks now and I love it. I feel like I’m finally in my true element. But that being said, it’s also been an adjustment. In fact, I learned a few lessons in my first four weeks — some lessons I knew, but were reinforced; and some of that surprised me. Today I offer you the lessons I have learned (so far) going into business for myself.

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1. Develop a thick skin. Working for yourself is kind of like being in sales, you’ll probably get dozens of “no” answers before getting a “yes.” You have to be okay with that and know it’s part of the process. You may feel like you’re pounding the pavement for nothing. But you’ll be surprised where opportunities come up.

2. Don’t take every job and know your worth. As you start out on your own, you’ll be tempted to take every business opportunity that comes your way because you don’t want to pass up income. While it’s important to keep your financial goals in mind, also know what you are willing to do and not do — and stick to it. I believe that if you know your strengths and play to them, soon enough, you won’t have to consider every project.

3. You will lose “friends.” You’ve probably heard that when alcoholics become sober, many lose friends because said friends are not comfortable with the new sober lifestyle. Sadly I’ve found this to be true as I’ve become self-employed. For reasons I cannot understand, individuals I once considered friends are no longer so. It’s a harsh and sad reality, but it has made me realize the true meaning of friendship.

4. Start thinking of money differently. For someone that’s had a steady paycheck every month, it was tough knowing that many months won’t have that same amount in the bank account. You have to be okay with this. A few years ago, the thought of financial uncertainty would have ignited a panic attack. But I am now comfortable with the unknown, and I only focus on the present and moving forward.

5. Your house will not be cleaner when you’re self-employed. I think my house was the messiest it ever was during the first week of being self-employed. Dirty dishes lingered. Toys and clothes were everywhere. Laundry was piling up. It was not pretty. You think because you’re working at home, you will be taking breaks with a duster in hand. No, that doesn’t happen. I just learned to ignore the mess and work, work, work.

6. There is an adjustment period with finding the ideal schedule. And I’m still trying to figure it out. My entire life, I went to an office in the morning, worked until 4:30, left to pick up Sophie and then started my evening at home. When you’re self-employed, that all changes. It’s tough to find the perfect schedule. Give yourself a break if you haven’t figured it out yet.

7. Remember your old work habits that worked. I manage my time and projects the same way I did in my office jobs for 15 years. Every day I start with a “to do” list and work off that list (which includes projects, writing, email, social networking, etc.). And then at the end of the work day, I re-evaluate the tasks and write the “to do” list for tomorrow. It worked for me for 15 years. It will probably work for 15 more.

8. Get used to people thinking you don’t really work. Some people have a tough time understanding that you can sit at your computer for six to eight hours a day and actually work. Get used to those people thinking there’s no way to work from home and just ignore the comments. There’s really nothing else to say. You know you’re working because if you don’t, say good-bye to self-employment.

9. Get the right insurance protections. When I worked full-time for a company, I had all the insurance plans (life, disability, health, etc.). While I still have health insurance thanks to Bryan, my life and disability insurance disappeared as they were group policies. Even before I left my job, I started the process of getting life and disability insurance. I would not be fiscally – or personally – responsible if I didn’t make sure my family and I were protected.

10. Plan downtime. I’m still working at this one, but I’ve already seen that it’s important to plan downtime. Especially when you work from home. It’s easy to work 24/7 since you’re working for yourself and the computer is always available. When you start up, you will likely find yourself working more than you did in a 40-hour-a-week job. But for your own sanity – and the sanity of your family – plan time off for yourself. Take your weekends. Have a fun day with the spouse, kids or friends. You’ll probably find yourself more productive afterwards.

So there you have it: ten lessons I’ve learned while being self-employed. To those of you planning to one day do the same, remember these tips that will hopefully make your transition easier. And while the first four weeks of my new endeavor have been tough, they have been the absolute best four weeks of my life.

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41 Comments leave one →
  1. April 9, 2012 3:25 am

    Wow, you’ve figured out a lot in a short time. I don’t get the friends issue at all! Are people envious that you’re “not working” in their minds? I’ve had that response (from one sister…).
    Keep up the great work! Hey.. an idea I’m tossing around– interviewing bloggers, one a week- what do you think? I’m thinking it might be a way to boost book site traffic (forget about sales…). I’ve been doing author interviews on sites that interview authors and thought the blogger idea might be fun. Also, check out National Women on the Rise.

    • April 10, 2012 10:25 pm

      Great idea for the blogging interviews! Let me know when you want to do it.

  2. April 9, 2012 5:38 am

    You obviously made the right decision Leah as you have learned so much in such a short period of time! I think a lot of it had to do with your wisdom and maturity level going in, but I am so proud of you for making this move and showing mum’s the world over that it can be done. You go girl!!!

    • April 10, 2012 10:26 pm

      Thanks, Elizabeth! I appreciate your support.

  3. April 9, 2012 6:51 am

    It’s wonderful to hear that these four weeks have been the best in your life! I’m so excited for you, what an exciting new beginning. Thanks for sharing the tips — I hope one day I have a reason to revisit them 🙂

    • April 10, 2012 10:27 pm

      You will do it one day, Caryn! I know it and I know you! Thanks for your nice comments.

  4. April 9, 2012 7:16 am

    Good tips for us stay at home workers Leah. The best advice that was given to me was to schedule your working hours the same as if you still had a job – say Monday-Friday from 9-5 and to still take weekends off. Like you said, it’s too easy to work all the time. I’m still not heeding that great advice, but I’m using it as a goal that I’m working towards, cuz I can see how easily you will get burned out otherwise.

    • April 10, 2012 10:27 pm

      This is so true, Susan! I’m definitely trying to achieve that balance. Like you said, it’s tough. But it’s doable too.

  5. April 9, 2012 7:31 am

    I have not been self-employed but I did work from home for a year when we moved from TX to MI (my employer kept me on as we transitioned through a merger). I had to adjust to people thinking I had all kinds of time available b/c I was home all the time – not true. Also had to adjust to the fact that I was on E.T. while my HQ was on Central. And .. it was hard to learn a new city when I was tied to my desk at home — but – having done it, I will say that it was a fantastic experience, all in all. Good for you for not being too hard on yourself about a clean house — that one is highly over-rated :).

    Good luck!! I’m so happy that you are (mostly) enjoying it and not at all surprised to learn that you were careful and prepared 🙂


    • April 10, 2012 10:29 pm

      Thanks, MJ! The east coast vs. another time zone is tough too. Since I’m on the west coast, I have seen the work and online traffic really die down after 2:30. And yes, people do think you have so much time when you work at home. Not true at all!

  6. Erin permalink
    April 9, 2012 7:39 am

    Working from home, even for a company, has many similarities. I’ve done it for 11 years and am still constantly readjusting the schedule, downtime, etc. And my house is a mess! I’m home to work, not clean 🙂

    I think it’s awesome that you took the risk to go out on your own. I’m glad it’s going well!

    • April 10, 2012 10:30 pm

      Thanks, Erin. You are right that we face similar challenges with scheduled and such. And I’m glad someone else doesn’t feel that their house has to be perfect either.

  7. April 9, 2012 7:39 am

    I wish I’d had these realizations as early on as you’re having them! These will save you a lot of headaches and heartaches down the road. And you’re definitely getting the hang of it!

    • April 10, 2012 10:30 pm

      Thanks, Susan! You have been an amazing mentor and I appreciate it so much!

  8. April 9, 2012 7:57 am

    Your 10 lessons are priceless! I am not sure if I would be able to ever work from home – I would find every excuse to procrastinate work…..

    • April 10, 2012 10:31 pm

      It’s all a matter of focus, I guess. But I admit, most of the times I have to force myself to stop and pick up Sophie. I get pretty focused.

  9. April 9, 2012 8:10 am

    Great advice. My situation is a little different from yours, but I definitely need to absorb your lessons – especially the ones about time management. You’re so organized and prepared that success seems inevitable for you. Sorry to hear that some “friends” have abandoned you. It seems so strange. I’d have thought everyone would be cheering you on.

    • April 10, 2012 10:31 pm

      Thanks, Shary. I appreciate your nice words. The friend thing is tough and complicated. But I know it’s for the best.

  10. April 9, 2012 8:20 am

    Congrats to you, Leah, for making the leap. I have been self employed for 9 years now, and all your tips are valid and spot on, especially the one about finding ‘down time’. We do tend to overwork.
    Even after 9 years I am still working on losing the fear over the sporatic paychecks. I deal with it by building a savings to fall back on during ‘lean’ times, or times when I am unable to work, for whatever reason. And then I stick to a budget (it’s easy to overspend during flush months).

    • April 10, 2012 10:32 pm

      You are so right, Cynthia, about sticking to a budget. I’ve found that the uncertainty has really helped me not buy certain things though. In a way, it’s a good motivator for me to save as much as possible.

  11. Lorena permalink
    April 9, 2012 8:26 am

    I’m so glad you’re enjoying your new gig, Leah! And I can’t believe that some folks have turned out to be not-so-friendly… That’s honestly something I would not have expected.

    Anyway, keep on keepin’ on with all your great work!

    • April 10, 2012 10:33 pm

      Thanks so much, Lorena! I appreciate your support. The friend thing is weird and I hope others don’t have that issue so much. But it’s a reality and I’m dealing with it. As you can tell, everything else is great.

      • Lorena permalink
        April 16, 2012 11:58 am

        Hm… I never had any issue with my friends when I did freelance work, but I still kept my day job — and it was while we were furloughing, too, so it seemed like everyone at work had a “job on the side” at the time.

        Oh well, as the kids say these days “haters gonna hate,” so don’t let it get you down! 😉

  12. April 9, 2012 11:28 am

    You are a quick study, Leah! I’m sure you’ll get all the laundry and scheduling details figured out before you know it…You’re a real inspiration!

    • April 10, 2012 10:34 pm

      Thanks, Diane! I appreciate you cheering me on! And we’ll see about the laundry. My solution may be teaching Sophie to do it earlier than I expected 😉

      • Lorena permalink
        April 16, 2012 11:55 am

        My parents taught my sister and I how to do our own laundry as soon as we were tall enough — with the help of a step-stool — to push the buttons! Of course, when you’re younger, the idea of self-sufficiency is very exciting, so I have no doubt Sophie would love to learn.

  13. jolinapetersheim permalink
    April 9, 2012 4:17 pm

    This post really spoke to me, Leah, as I am now a “self-employed” mommy who is also trying to relearn my writing schedule. Thank you for the tips about juggling downtime and work time. I hope I figure out the patttern as quickly as you did!

    • April 10, 2012 10:35 pm

      Thanks, Jolina! You will do great. I’m sure you can give so many great tips on managing a newborn and full-time career as a mom with writing. I’d love to hear what you learn!

  14. April 9, 2012 4:19 pm


    So great to hear this from someone who, like me, has spent their entire professional career in the office, versus at home. You made the transition I hope to someday make myself. Your tips have given me lots to think about, and really consider if I can pull it off (my plan is to be a part-time published author, part-time freelancer/consultant). I’m very anxious to hear how your new adventure develops, so please keep us posted! And thank you for sharing these great lessons.


    • April 10, 2012 10:36 pm

      Shari, I know you are so close yourself! You are an amazing writer and social media expert. I know you’ll be fabulous when you make the leap. You can do it!

  15. April 9, 2012 8:50 pm

    What a great list! I can tell this was the right move for you. And that first cartoon was great! 🙂 Congratulations on your month of self-employment. I hope many happy days are in store for you, and wish you all the best!

    • April 10, 2012 10:37 pm

      Thank you so much! It certainly does feel like the right thing to do. Thanks for your nice words.

  16. April 9, 2012 9:14 pm

    So proud of you, Leah, in taking on this new chapter of your life, but also being so wise and reflective on the pros and cons. Like others, #3 was the surprising insight. I guess that some of those “friends” were really colleagues, and one thing I’ve learned is that there are those who like you for who you are, and those who like for what you are. Like you said, it makes you know who the real friends are. For the record, I have always liked you for who you are. So stay true to yourself and I wish you nothing but tremendous success. You are an inspiration for the rest of us.

    • April 9, 2012 10:18 pm

      Leah, your 10 tips were wonderful! And from your strength and happiness you’ve shown, you definitely have made a wonderful choice. Your writing is always right to the point and I like that 🙂 During these short four weeks you have come to know SO much. I’m proud of you as writer and a self-employed daughter. You’re great, Boo, I love you ❤

      • April 10, 2012 10:38 pm

        Thanks, mom! Here’s to many more great weeks to come!

    • April 10, 2012 10:38 pm

      Sharon, what a nice comment. Thank you! The friend thing is odd and it was a disappointment, but hopefully it was a rare case and others won’t have to deal with that tip. I really appreciate your support and touching words. Thanks!

  17. April 11, 2012 8:56 am

    Leah, this is probably the BEST advice I’ve read from someone who works for themselves, from home. Thank you, thank you times a zillion!

  18. April 12, 2012 8:24 am

    What an amazing list and helpful advice. You’ll help alot of folks by telling them your experience and lessons as you go along. Well done! Thanks for sharing. I wish you continued success. 🙂

  19. April 14, 2012 8:16 pm

    it’s wonderful to hear that you are able to do what you love! wishing you continued success 🙂

  20. October 30, 2012 8:53 pm

    Great running into your blog – a bit after you wrote this but very beneficial. I’m 3 months into self-employment and can echo everything except the friendship part – because for me as a non-parent, I actually have more flexibility to see my friends who have kids or who are also self-employed 🙂


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