A month ago today, I was supposed to go back to being a teacher. Instead, I chose to be a solopreneur.
The past month has had its ups and downs. My web design business has been going great. I received an overwhelming positive response for Riding Solo (thank you for that!) I even had time to start brainstorming some new projects I plan to unveil within the next few weeks.
However, I haven’t felt alive. Something is missing and I think I know the culprit.
The Number One Reason People Choose to Be a Solopreneur in the First Place
I’ve had the opportunity to ask many people why they decided to leave their jobs to pursue solopreneurship. Want to know the number one answer I heard?
“I wanted freedom.”
And yet, too much freedom is what’s killing me.
Why Too Much Freedom is a Problem
Too much freedom leads to procrastination. Which in turn, leads to not getting shit done.
Right now, I’m working haphazardly. I stay up late, sleep in, don’t eat because I’m too lazy to cook, and have no routine whatsoever. This lack of routine is taking a toll on my productivity and I need to do something about it.
How YOU Can Help
What is ONE piece of advice you can give me (and other solopreneurs) about getting into a routine?
Tell us your one tip in the comments below. Then, share this on Twitter and Facebook…..every piece of advice helps 
Photo by Joe Lanman
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{ 40 comments… read them below or add one }
I can’t wait to see what people say – I have been having the SAME problem. The biggest thing that helped me was setting up an office, separate from the rest of my house, and making my time in here my “work” time.
Having an office is HUGE. I have one but it’s a mess. I really need to make it work better for me. I may be heading to IKEA later today….
Read The War of Art by Steve Pressfield.
Every word.
I did. And it didn’t work. :-/
A schedule. Set yourself a schedule that can be flexible, but that the boss (you) can enforce. Want to watch that tv show? Write an article. Lunch with the girls, get a rough mock-up of that website that’s due later in the month. And schedule in fun stuff, or leave enough room so that you can have a goof-off day occasionally, but without falling behind.
That’s a good take on it, Megan. Breaking up the day with work and fun could definitely make it easier.
Nina,
I will tell you what worked for me. I can tell you are excited about going solo. I also can see you have the skills to make a go of it. The only thing stopping you is you. Before you think this is some new age mumbo-jumbo, let me explain. When you were a teacher you got up at a certain time (whether you felt like it or not). I’m sure you had lesson plans and other scheduling constraints. So basically, you established a routine and you stuck to it because that’s what your job required. I will admit what many entrepreneurs and solopreneurs probably will never say in public. Sometimes you just don’t freakin feel like it! But the difference between this and your former career is if you drop the ball nobody will say anything. After a while you will notice you are making less money and you have fewer blog comments, etc. So, what worked for me is realizing that this is what I want to do so just do it! Of course some days you may take the day off. But the buck stops with you so keep at it. Just remember that you’re doing what you love so it should be fun (most of the time). I also agree with Jennifer. We have to treat our solopreneur careers seriously..you know like real businesses with hours and deadlines and stuff? Sorry for the long post but I experienced the same thing not too long ago and wanted to share in case it could be helpful. Best of luck to you!
Thanks for sharing, Anthony. You’re 100% right. Sometimes it’s easier said than done though. My rational brain knows I need to work even though I sometimes don’t want to. However, it’s just too easy to procrastinate when I’m home.
One thing that has been working is just getting started. I learned that from this post by Leo on Zen Habits. It has really helped.
I think this is something that stays around forever. You are no longer on the world’s schedule. I can’t imagine how difficult it is for you transitioning from a job like teaching. I have basically always done my own thing.
Adopting a schedule is super difficult when you don’t *have* to adopt one. You could work at any time.
The first thing I did was decide when I actually like to work the most. I can work from 9pm to 4 or 5am, but do I really like that? No. I hate that.
The next thing I did was have food and drinks in the house. That sounds weird, but if you’re hungry and don’t have food you have to leave (and therefore not work).
Then I went through a punishing process of resetting my sleep schedule. I love working in the morning until the early/late evening (we’ll say 7:30-8pm is when I like to stop). So I started getting up around 6:30-7:30am, showering, getting dressed-ish, making coffee and breakfast, check news, etc. I get to work around 10. I take my sweet ass time
I got rid of cable. That was crucial. I hate noise anyway. Music, tv all of that bugs me to death when I work. I want absolute silence.
Last, I want to be alone. I can’t think about the complex interactions of thousands of lines of code with people bugging me. Presently, my wife is not working because we just moved to Austin, TX (yay us!). But, she’ll get a job soon. I love her to death but I need to be left alone.
Anyway that’s my two cents. Don’t beat yourself up over this, either. I did that for a long time and it only makes it worse. Just recognize it as a simple task, just like getting CSS floats right, and do it!
Ahhhhh, CSS floats?!?!?!?! That made me want to take today off
In all seriousness, you’re tips are great!
I definitely beat myself up over it (which I’m sure MANY people do). I think it may help to compare it to going to the gym. If you miss a day, don’t stop exercising completely. Just wake up the next day and get yourself back to the gym.
Missing one day isn’t going to make all of your efforts pointless.
Congrats on the Austin move! Now you can bug Chris whenever you want
Matt G,
I think you are right. Some days are better than others. I think the biggest thing you bring up is not to beat yourself up. If you plan to complete three tasks but you only get two finished, don’t be too hard on yourself. It’s a constant struggle but I wouldn’t go back! Deciding your optimal schedule may take a while but it’s worth it.
Excellent question! I live in Moorestown and my main client is in Plymouth Meeting Pa. I am home working mostly (not regular hrs) and out there several days per week. I have noticed that I am generally more productive when I am out there, and have wondered why (cause it’s 3hrs on the road per day!). In my case it seems to be a combination of focus and human awareness. Meaning I would rather be around ppl even if I am working obliviously (which I don’t really do for too long). At home I can definitely focus but there’s this weird sense of loneliness and isolation that I am aware of (not to mention the puppy who wants some attention). I develop software. Yet I find the coolest parts of that to be very social and collaborative. Indy Hall and formal shared spaces may help- I have never tried it. But I am wondering about less organized local workgroups (Starbucks, someone’s home/office etc) for occasional contact.
Thanks for bringing up the co-working option, Greg.
Does anyone go to a co-working space and see it increase your productivity?
I’m still unsure if co-working groups really increase productivity or if they are better used for networking. I’ve never been to one but wouldn’t mind trying it out.
As far as Starbucks, Panera Bread, etc. go, I either am super productive or get absolutely nothing accomplished. It’s hit or miss for me. But again, would love to hear other people’s experiences with that.
Would you rather go back to your old job than enjoy the freedom of being self employed? Because unless you get off your ass and work, you’ll run out of money and have to beg your boss for your old job back. And doing that would mean you failed. That’s my motivation.
That’s great motivation, Dave. I think my problem is that I’m working just enough to make the money I need but not enough to make the extra money I could have.
Set tight deadlines and don’t let them slide. If it weren’t for deadlines, I’d never get anything done! Take on more work or start a fun side project if there’s still too much unstructured work time.
Also get dressed for work every day. No house pants! Puts my brain in the right mode every time.
The transition is tricky but you’ll figure it out!
Great advice, Joanna. Getting a shower and getting dressed (just like you would for any other job) is important. I definitely get more done when I do.
Nina,
First of all congrats on making the leap from teacher to solopreneur. Secondly, congrats for being totally honest with yourself.
I recommend finding a mentor, or someone else in a similar situation who will hold you accountable for meeting your goals. If you know you have to “report your progress” to someone you respect, I think you will feel more motivated to get things done.
I also recommend rethinking your to-do list. Rather than wrapping an entire project or task into one to-do item, break it down into smaller, more manageable tasks. Each day, before you start work or check your email, look at your to-do list and decide which top 3 you will complete before the end of the day. Remove all distractions and work for about 1-2 hours non-stop on each task. You will feel a sense of achievement and progress when you can check off several items on a daily basis. It should help to keep you focused and on target with your goals.
Wishing you every success with your new venture!
Thank you so much, Linda!
I totally agree with you about the to-do lists. Loading them with too many tasks is just setting yourself up for failure. Narrowing it down can really help you focus and achieve your goals.
I have lotsa tips, but I can start with this.
Remember your “enemy” is not freedom, but procrastination. Trust me to get over that, it’s going to be a lifetime battle. Therefore, we (I love reminding myself too) shouldn’t see it as a destination, but as a journey.
How?
The answer is simple, but the process is not. By having a productive lifestyle. Physically and mentally committed to the lifestyle of not wasting time plus producing and creating.
Start small by doing what matter’s now. It doesn’t have to be something related to Riding Solo, it could be anything. Then, commit to it. See if it’s something that can be turned into a good habit or routine.
As an example, I am an aspiring reader of your story and blog. I am NOT in the position where I could have it right away, so I start doing what necessary for me to serve food on my table, but at the same time, trying to earn the freedom inspired by people such as yourself.
Next, when you are mostly in control of your decisions and not lose out to distractions like TV or twitter, you want to gain more momentum (or simply, be more productive). So I believe we all know why we want to keep this momentum but the issue now is how.
So I identified some of the reasons why I might lose sight or side-tracked;
too busy with too many things (prioritization issue)
simply forgot or distracted
________________(Fill that in)
What I did to counter this, is by keeping track of my activities or momentum. There are many ways and I believe a lot of us already share their ways of doing this (todo lists etc.).
Don’t let this takes too much of your time, and becomes your workload. You don’t want it to be abandoned because it’s tedious and takes a lot of time just to “keep track of what I should be doing”. So the idea is to keep it simple and in sight all the time (esp if you are easily distracted like me!). Find what works for you too.
I’ll share on how I do this, in hope it helps give some ideas and concept of this. I have sync’ed todo lists on Evernote (from iPhone to workstation) so I see it everywhere. Been inbox-zero for 2 years and that becomes my todo lists too.
And about that momentum going thing, I created a spreadsheet on Google Docs that keeps track of my daily, weekly, monthly and yearly goals (or to do/become, whatever we wanna call it).
From the images I shared above, I have the same exact problem you are having back in July! But the fact that I keep it visual and tracked/logged, at least I am aware of my activities and momentum. I was seeing too much red and I tell myself if I am not gonna start now, and get myself some discipline, 2011 will be a waste.
Then I start small by investing small hours on my self-learning programming goal, week in week out. By the time I read this post, I noticed it’s been 10 consecutive weeks of “green” and doing things that matter. And as you can see, the table is so simple it shouldn’t take more than 10 minutes to create and every week, I just have to color each box with either red or green (which would take 5 seconds at most).
See when it’s a lifestyle you believe in, you will have almost zero concern on getting back into laziness or procrastination loop. I bet it’s “normal” that we become inspired and productive every once in awhile, then get back into our “normal” procrastination mode most of the time.
Look forward to read about how you will tackle this and what’s work for you. Keep us posted!
Thanks for sharing your insight, Ajmal. It’s great to have something visual to try and see how and where your time is spent. I wish you luck in your Riding Solo aspiration!
I came across this Inc. magazine blog post on productivity and procrastination not long after you posted about it here so I figured I would share. Lots of good ideas here as well. http://peterbregman.com/inc-magazine-interview-mastering-distraction-in-18-minutes/
Awesome! Thanks for sharing!
Hi, Nina. Not a solopreneur YET, but I agree that setting an alarm, getting up, showered, and dressed (in not total bum clothes) helps me focus. Then, enjoy the “luxuries” of being home–tv/news/newspaper/coffee/etc– then set a goal of being in your work chair by a certain time each day and working until a certain time. Factor in meals. Stop a few hours in for a light lunch. Work some more. Put casserole in oven for dinner. Throw in loads of laundry. Check how much you crossed off your to-do list. Eat dinner. Go to yoga. Drink a beer. Watch tv. Sleep. Repeat.
Getting a shower first thing in the morning seems to be a common response. I really should try it
Setting a time to be “in the office” just like a traditional job can really help. Consistency is key when setting up a schedule.
Thanks for dropping by, Fifi!
Hi Nina! I just found your site through Jenny Blake, and I’m looking forward to following your journey! I’m not a solopreneur yet, but I do have a few projects going on the side, mostly related to writing and adventure-based learning.
I was actually discussing this issue with a friend of mine, and he shared his strategy: he doesn’t let himself eat until he can cross something off his list. So he can’t eat lunch til he’s finished a specific amount of coding, or he has to have a clean kitchen before he eats dinner. He talks about this here: http://samgrossberg.com/new-lifehacking-strategy-reward-with-food. This doesn’t work for me, as I get hungry if I wait too long to eat, but perhaps it’s worth a try for you?
Cheers,
Heather
Thanks for dropping by, Heather! That is a pretty good idea. I’ll have to try it out and see if it works for me.
Hi Nina! I have passed the 15 year mark as a Solopreneur! Here’s what works for me:
1. Keep an office separate from my work space. (My husband is actually the one that insisted on this.) He says I’m in a different mode when I work, and…no surprise…not that fun to be around when I’m thinking that way. My office is in the basement. Often, just getting into that space launches me into work.
2. Stay plugged into your financial progress. Look over your pending work and your payables as often as you need to so that you feel your need and your power to make money.
3. Commit to deadlines outloud in conversation, or written in emails and proposals.
Great suggestions, Christine.
The second one is really important. Once you start keeping tabs on how much money you are making (or losing), it starts to light the fire under your butt!
Hey Nina, place a value on the tasks at hand. It seems as though some parts of being solo are uninteresting to you in some ways. Like, I know people who love to cook and are great chefs but really can’t run a restaurant. Maybe the idea of having a planner or project organizer to take the menial or more formal aspects of your business that you don’t want to deal with will help. Work during the hours you feel most alert and comfortable…being unconventional is good. That’s who you are. Relocate yourself sometimes to places that offer what you need…Whether it’s solidarity or noisy environments. The key is to capitalize on the negatives if you can. Know what I mean…
Great advice, Kris. Relocation is key (if you work from home). Working at home one day and going out to a place like Panera another day is a great way to switch it up and keep you on your toes. Variety is the spice of life
Hey Nina — I recently heard Michael Ellsberg say sometimes it’s OK not to have a rigid schedule, which sparked an ah-ha moment for me. I think because the rest of the world is on a 9-to-5 schedule, we think we have to enforce something similar when we go off on our own. And for some people, that works. But for others, it’s perfectly OK to have a day where you switch from one thing to another to another and take care of tasks as they find you — so long as you’re actually productive. I write lots about what’s working for me in http://bit.ly//solosecrets. Great to connect!
You have a really good point there, Alexis. Society says we need to work 9 to 5, but being a solopreneur is already unconventional. Who says we need to uphold a traditional work schedule? I guess the trick is, we need to find our own schedule that maximizes our productivity.
Glad we connected, too!
I felt this same way about a year ago so I made an active effort to make major changes to my routine. Notable changes include waking up at 5am *most* days, I drink tons of water, I started learning new technologies (outside of WordPress/Thesis), and I also dropped off the face of the social web for most of the year (a trade off I made to win back some time to learn new technologies). As far as professional growth goes, this has been my best year by an Alabama mile. I continue to actively make changes to my routine(s) and I find it to be a great (quick!) way to positively influence other areas of my life.
It’s definitely a work-in-progress type of thing. I constantly find myself making tweaks to try and boost my productivity. I’m glad it gets better with time (and perseverance). Happy to see you are back in the social web – we missed ya!
Perseverance is the key. If I can survive the 720° turn it took to go from insurance agent to web developer, than anything is possible. Just strive to get better everyday.
Nice work here on the new site, btw! It’s nice to get back online and see all the cool things my friends have been up to!
Nina,
One thing I do is use an online countdown timer. If I need to do some writing, finish a project, etc, I will set somewhere between 20-40 minutes on the timer and will keep it open. The goal of the time set is to ONLY work on the project/blog post/etc that you need to. Nothing else.
Watching the precious seconds tick down puts a sense of urgency in my work and motivates me not to check Facebook/Twitter/E-mail during that time. Once in a while I will even use Facebook as a carrot, telling myself, if I work the entire timer length, then I will check Facebook after (timed of course).
Give it a shot! Let me know if it helps – here is the timer I use: http://timer.onlineclock.net/
Take care,
Dan
PS – Awesome site design!
Hey Dan, thanks so much for the timer suggestion! There are a ton of distractions that take a toll on our productivity. Dedicating time for single tasks is important – especially with the social media frenzy that is out there! I love the idea of a timer and a “carrot” for when you’re through. Can’t wait to try it out! I’ll keep you posted.
This is a very common issue with every freelancer. Initially when I started working I felt like I was working more than I could and getting exhausted. Then there were days when I won’t feel like working because I wanted a break.
A simple rule I followed was “5 days a week + a daily schedule”
I have put up a white board near my desk where I put up the list of “things-to-do” in order of their priority + expected time for each task. And clean it off at the end of the day.
Above all, I like to work late at night just because there are no social distractions. It’s all “me and my work” kind of world. This has greatly helped me in increasing my efficiency.
I now have that issue – working TOO much. It’s so crazy how freelancers have a problem with that. Having a schedule is really important to ensure you aren’t working too much or too little. I’m also a night owl, but I find that I work better during the day. It’s all about doing what works best for you. Thanks for sharing your thoughts, Puneet
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