How to Start a Freelance Side Job While Working Your Day Job

There’s no question that working as a freelancer can be highly rewarding.  As a freelance writer, seeing my name on industry websites and hearing positive feedback about my work gives me a warm fuzzy feeling that I’ve never been able to capture working for others.

Now, unfortunately, I can’t take that warm fuzzy feeling to the bank.  So for at least the next few months (while my husband and I pay down the debts that are preventing me from striking out on my own), I’ll be one of thousands of people around the world working a side hustle project in addition to my day job.

The good news is that I won’t be alone.  In a recent article The Economist notes:

Millions of workers are embracing freelancing as an alternative to full-time employment or because they cannot find salaried jobs.  According to IDC, a market-research firm, there were around 12 million full-time, home-based freelancers and independent contractors in America alone at the end of [2010] and there will be 14m by 2015.

–The Economist, “Work in the Digital Age: A Clouded Future”

But whether you’re running a side project to bring in extra cash, to fulfill a creative need that isn’t being met by your day job or in the hopes of becoming self-employed at some point, the reality of the situation is that balancing a side gig with a full-time day job is tough.

And it’s not just, “Oh, dear, looks like I’ll need to find an extra hour or two this week…” tough.  Balancing two jobs at once is, “How on Earth am I going to squeeze in another 8+ hours of work tonight without my spouse leaving me and my kids hating me” tough.

Of course, nothing in life that’s worth having comes easy, and we all know that there’s a pretty big light at the end of our tunnels if we’re willing to stick it out and double up for a while.  So what we need isn’t a pity party – it’s a set of coping strategies that we can use to stay sane and healthy until our efforts start to pay off.

And while I can’t claim to be an expert on time-management or stress relief, I’ve been a chronic over-achiever with more than one project running at a time all my life.  The following techniques are the ones I’ve found to be essential in surviving – and thriving – when juggling multiple priorities.  I hope you find them helpful!

Make Health a Priority

They say that, “Early to bed, early to rise leaves a freelancer healthy, wealthy and wise,” but how in the heck are you supposed to get to bed on time when you’ve got a project due at midnight and hours of work ahead of you?!

As freelance workers, it’s so easy to get so absorbed in our work that we push health considerations to the sidelines.  When you’re burning the candle at both ends, it’s easy to rationalize making compromises to your health – say, grabbing fast food for dinner for the fourth time in a week so that you don’t have to spend time cooking a meal.  Or maybe for you it’s skipping yet another gym session to make a little more progress on your latest project.

The problem with this mentality is that, as a freelancer, you have no backup.  Sure, at your day job, there’s someone who can cover your work if you call in sick – but who’s going to take over your freelance work if you let your health slip so much that you wind up sick or injured?

So even while you’re balancing a side business with your day job, it’s critical that you keep your health and well-being at the top of your priorities list.  Consider the following strategies for staying healthy while doubling up on your workload:

1. Sleep – get it!  If you’re one of those lucky few who thrives on 4-5 hours of sleep a night, good for you – I’m incredibly jealous…  But for the rest of us, getting at least 6-7 hours of sleep a night is crucial to staying healthy and producing good work.  If you can’t get it all at night, I’m a huge fan of the 20-30 minute power nap taken during lunch break at your day job.
2. Nutrition matters.  When you power your body with good food, you’ll find that you’re more focused and more productive – both of which are crucial to balancing a day job and a side business.  So avoid the temptation to slip out and grab a burger instead of cooking a healthy meal and watch as your work quality skyrockets.
3. Get moving.  Same deal as above.  Your body needs to move to stay healthy, and you’ll find that getting active at least a few times a week has a tremendous effect on your stress levels (which are probably high…).  It doesn’t have to be anything too strenuous (although I’m a big fan of kickboxing for working through day job/side business frustrations) – even walking around outside for 15-20 minutes can be hugely beneficial.
4. Consider ergonomics.  If your day job and your side business both involve computer work, you’re putting yourself at risk for over-use injuries related to spending all day staring at a screen.  Make sure your work stations are set up to minimize strain on your wrists and back, and take a break at least once an hour to give your eyes a rest.
5. Manage stress.  I know, I know – you probably think I’m joking right now…  But here’s the thing – mega doses of stress can wreak havoc on your health, leading to things like hypertension, insomnia and acid reflux.  Although you likely won’t ever be stress-free while working two jobs, it’s important to minimize it as much as possible.

When it comes to minimizing stress in your life, both sleep and exercise (as described above) will go a long way towards keeping you sane.  However, you might also find it helpful to take up meditation, yoga or some other type of relaxation practice to help manage stress.  Personally, I find getting regular massages and taking the occasional day off of internet work entirely to be beneficial helpful in this area.

Maximize Efficiency

I’m not one of those “gung-ho” productivity gurus who follows strict rules about email follow-up or file management, but I will say this – when you’re balancing a day job and a side gig, you don’t have the time not to be efficient.

Now, for the purposes of this section, I’m going to assume that you’re being a good employee and keeping your day job and side business completely separate (although I’ll discuss the ethical implications of the alternative later on in this article).  So for now, your biggest concern should be efficiency in your side business.

If you don’t feel like you’re being as efficient as possible, ask yourself the following questions:

• What aspects of my business do I spend the most time on?
• How can I handle these tasks differently to free up more of my time?
• Do the tasks I’m spending the most time on contribute substantively to my business’s growth and success?

Depending on your answers to these questions, you might find any of the following strategies helpful:

1. Batch process your tasks.  Batch processing refers to grouping similar activities together and handling them at once in order to maximize productivity.  Email is a great task to manage using this technique.  Basically, instead of checking your email every time that “New message” alert pops up, set a regular time at which you’ll check your messages (for example, the noon and 4:00pm checks recommended by Tim Ferris in the Four Hour Workweek).  If you make an effort to stick to your schedule, you’ll save a lot of the time you previously lost switching between tasks.
2. Eliminate unnecessary jobs.  Be ruthless in what you choose to spend your valuable time on.  Remember – just because some guru or strategist in your industry says you need to be doing something doesn’t mean it necessarily makes sense for your business.  If a task you’re doing isn’t contributing to the growth of your business, get rid of it and don’t look back!
3. Outsource whenever possible.  If there are any tasks to be done in your business that don’t require your personal involvement (and believe me, there are probably a lot more than you think!), consider hiring a VA to help manage your business.  Order fulfillment, financial reporting and market research are all good candidates for outsourcing using a VA you locate through a service like Odesk.com or Elance.com.

Now, a few words on outsourcing…  The thought of taking on another person to help run your business can be overwhelming to some freelancers – after all, aren’t you working for yourself to get away from the whole “employee-employer” relationship?!  If you feel that way, skip this section entirely.  There’s no reason to add an extra layer of stress to your business if it isn’t necessary and won’t benefit you.

But if you’re intrigued by the possibility of using outsourced workers to automate elements of your freelance business, read on.  Although external VAs aren’t a good fit for every type of business, consider the following examples of how I outsource elements of my freelance writing business in order to maximize efficiency.

1. Contracts and project follow-up.  Whenever I take on a new client or a new writing project, there’s a certain amount of follow-up work that needs to occur.  Contracts need to be signed and returned, and I need to gather details about what specifically the client is looking for (ie – what style/tone, what word length, what sources and so on) for his project.But instead of spending my precious writing time on this background work, my VA can communicate with the client and add contract details directly to my Remember the Milk account where I can see them – no follow-up needed on my part!
2. Background research.  If I’m writing on a subject that I’m not very familiar with, I’ll probably need to do some research work before I’m able to start writing.  But since I’d rather spend my time writing than slogging through potential sources – sorting the good from the “hasn’t-been-updated-since-1996” – I have my VA do the research for me and send over a neat list of good, informative sources to use on the project.
3. Billing and book-keeping.  Once I’m finished with a writing project, my VA can bill the client and follow-up if bills aren’t paid on time.  I also use the services of a bookkeeper to make sure that my expense statements are more organized than my former “receipts in shoebox” system.  A good CPA or accountant is also vital to ensuring that my tax obligations are met and that I don’t spend hours needlessly pouring over my tax returns every April.

Sure, there’s a little bit of time lost communicating what I want done with my VA, but since I generally follow a set of standard procedures, I only have to teach my worker how to do things once.  After that, she can handle the task repeatedly in the future – giving me more time to spend on my writing.

For a more thorough guide on how I found my current VA, check out my case study on Outsourcing Effectively.

Improve Effectiveness

So, efficiency’s one thing.  Making sure you’re accomplishing tasks as quickly as possible is vital to running a successful freelancing business.

But what if you aren’t working on the *right* tasks?  Does it matter how efficiently you mark off items on your to-do list if you’re filling your time with junk work in the first place?  This is where effectiveness comes into play.  Let me give you an example to clarify what I mean…

I work as a freelance writer.  That means that in order to get paid, I need to do three things only:

• Submit proposals to clients to get hired,
• Write the content they’re looking for, and
• Send invoices to bill for my completed work

Now, do you know how much of my time is spent on these three tasks, compared with all of the other things that occupy my time?  Although it’s hard to say for certain, I do spend a pretty large chunk of time doing things like updating my website, communicating with my colleagues and clients via social networking sites and checking my email (for the thousandth time in a row…).  None of these things put money in my pocket directly, which makes them ineffective uses of my time.

Here’s how to determine whether you’re spending most of your time on effective work or not:

First, invest some time in analyzing the tasks you complete on any given work day.  Free apps like Rescue Time can be useful in completing this exercise, but it’s enough just to jot items down on a sheet of paper if you prefer.  Don’t try to structure your time any differently than you would on a normal day – just try to be aware of the things you’re spending time on.

Once you have a list of the tasks you do every day, go through the list and mark off those that actually put money in your pockets.  Be honest with yourself – chatting with your buddies on Twitter might lead to some business connections down the road, but for the most part, it’s time that could be better spent on tasks that result in income or substantive business growth.

The following are a few examples of effective tasks that will help you achieve your business goals:

1. Getting leads.  Again, saying that you need to get leads for your business isn’t giving you permission to spend hours goofing off on Facebook or Twitter.  Instead, focus your efforts on the actions that have led to successful projects in the past.  For example, this could be cold-calling businesses in your area, emailing website owners who could use your services or asking your current clients for referrals.
2. Making sales.  In most cases, closing a deal won’t be as simple as asking for the business – you might need to submit work samples, provide requested information or set up follow-up calls with potential clients.  Because these tasks contribute directly to your income, it’s a good idea to spend the majority of your time here, rather than on tasks with a less measurable impact on your bottom line.
3. Testing new procedures.  Testing and tracking – aka, the process of using qualitative data to determine what works and what doesn’t work in terms of growing your business – is a vital task for any freelancer.  Possible items to test and track include experimenting with new forms of lead generation, analyzing web analytics data and making changes based on your findings, or implementing new sources of advertising.

Personally, I try to follow the 80/20 rule as closely as possible.  That is, 80% of my time is spent on the tasks that I have determined result in income and measurable business results, while the remaining 20% is occupied by fun tasks, or tasks that might (but probably won’t) lead to business down the road.

Try this exercise for yourself and see if you aren’t amazed by the results.

Maintain Your Relationships

Another thing you don’t want to neglect while you’re ramping up your freelancing empire is your personal relationships.  Here’s the deal – relationships take time and effort to maintain, and if you fail to put in this work, you might just find that those relationships aren’t there anymore once your workload finally lets up.  Here’s who you need to remember:

1. Your spouse.  You know – that person you promised to love and support?  Well, if you spend all evening after work tied to the computer desk, working on your side business, there’s not going to be a lot of loving or supporting going on…
   Now, I’m not going to say that balancing your marriage with your business demands will be easy, or that your spouse won’t resent having to shoulder an extra household burden while you’re busy working.  There will be stress, but the best thing you can do for you and your spouse is to have an open, honest discussion about your expectations and your business timeline – specifically, your expected exit deadline for making the leap to full-time freelancing.
2. Your kids.  I don’t have kids myself and can’t comment on how to balance these relationships with your dual job situation; so instead, I’ll turn this section over to Harry Chapin.  Go listen to “Cats in the Cradle” a few times and see if that doesn’t make you want to turn off the computer and hang out with your kids for a little bit. J
3. Your friends.  It’s incredibly easy to let friendships deteriorate while you’re pulling double duty, but try to avoid this as much as possible.  Having strong friendships will give you an outlet for stress besides piling it all on your spouse and will help you keep an eye on the bigger picture.  You’ll also need these relationships even more when you go full-time and lose the social support system of your day job office.

Ethical Considerations

Earlier, I said that I’m assuming you’re being a model employee and not touching your side business work while you’re on the clock at your day job.  But let’s be realistic here – there are times when you absolutely must send out a business email or take a business phone call during regular work hours.

Here’s how to deal with these conflicting situations:

1. Understand your company’s policies.  Day job employers vary dramatically in their willingness to accept employees’ side gigs.  Some companies have “all in” policies that prohibit employees from taking on any work outside of their day jobs, while other bosses are more permissive, allowing side work as long as any day job work is completed first.  Typically, you should be able to find any such policies in your employee handbook.
2. Keep your work to yourself.  Unless your employer is completely open to outside work being done during business hours (and unfortunately, you’ll find it tough to ask this question in the first place!), it’s best to keep any information about your side gig to yourself.  It’s tempting to share your burden with your office gossip buddies, but do your best to stay quiet.  The wrong person catching wind of your side activities could result in some serious negative consequences.
3. Understand the risks.  While I can’t say that you shouldn’t do side business work at your day job (as that would be incredibly hypocritical of me!), know that you might be fired for doing so if your boss catches on, or if your corporate IT department notices and tracks any side business-related website visits.  If you aren’t comfortable with these risks, keep your day job work and your side business work completely separate.

What is your exit strategy?

Finally, one of the most important things you’ll want to consider when juggling a side gig with your day job is an exit strategy.

Are you planning to keep up this schedule forever?  If your goal is to eventually freelance full-time, by what date do you want to make the leap?  Knowing that the challenges of working two jobs at once will be short-lived – as well as remembering why working as a freelancer is so important to you – will help you to get through this hectic time with your health, your sanity and your relationships intact.

Are you balancing your freelancing business work with a day job?  Do you have any other advice to offer beginning business owners who are just setting out on this crazy journey?  If so, please share it in the comments section below!

Sarah Russell is a workaholic who currently juggles a day job in marketing with side projects as a freelance writer, an affiliate marketer and a blogger over at Common Sense Marketing. Check out her free series on How to Start an Article Writing Service.