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10 Strategic Questions to Ask Before You Become a Freelancer

Posted July 11, 2011 in Getting Started

Becoming independent is going to be the best thing you’ve ever done for your career–if you do it right. Not everyone is meant for, or even comfortable with, working on their own. It’s important to figure this out before becoming enamored with all the freedom freelancing brings.

You don’t want to leave a good job and then realize too late that freelancing isn’t right for you. So, make sure you ask yourself these questions first in order to determine the answer to the most important question–should you freelance?


1. Are You Comfortable Working Alone?

Freelancing can be a lonely job, and for some people that can actually impede their workflow. You’ll quickly learn that you miss the camaraderie between co-workers. You’ll no longer have free lunches, picnics, or any of the social events that come with a job.

However, if you’re like me, you actually prefer to work alone anyway. I’m actually sitting in my husband’s office as I’m writing this post and finding it very difficult to concentrate because there’s always several people coming in and out of the office to ask him questions. This is a great reminder of why I prefer to work alone.

However, it’s smart to have a couple of backup places to work from outside of your home office. Regardless of whether you like to be alone or not, it’s healthy to get out and have some human interaction. Personally, I always schedule my blog writing days on Wednesdays, when I take my laptop to a bookstore, Starbucks or to my husband’s office.

2. Are You Naturally Motivated or a Procrastinator?

Freelancing is going to be very, very tough for you if you’re a procrastinator. One of the biggest complaints that my clients tell me about their previous freelancer is that they never met their deadlines and schedules. This is one of the most important aspects of running a business. If you can’t deliver work on time you become untrustworthy and unreliable and you’ll likely end up without any clients.

However, if you’re a naturally motivated person, you’ll find that freelancing is a much better fit for you than working at a job. You can go out and find your own work and schedule yourself to work at your own pace. Just remember, reaching deadlines is as important as the quality of work you bring.

3. How Much Money Do You Need?

Before you decide to jump into freelancing, you need to figure out how much money you need in order to make the minimum payment on all of your bills. From this, you’ll have to decide how much to charge hourly and how many hours you’ll need to work a week.

You’ll also want to look at how much money you want to make. One of the biggest perks of going freelance is that you can control how much money you can make. Just because you only made a certain amount at your previous job doesn’t mean you  have to be stuck with that amount as your income. In fact, you should aim higher–maybe even double the amount you made as an employee!

4. What Are Your Skills?

What are you going to do when you freelance? Are you going to still do the kind of stuff you do now at your job? Or do you want to try a different field? Figure out what kind of skills you have and what would really make you happy. Then hop online and do some research. Is there a market for your skills? If not, could there be a market for something you are good at doing?

5. What Kind Of Work Do You Want to Do?

This question will dictate how you run your business. While it’s possible to change your field mid-course, it’s always easier to figure it out in the beginning and go after it. What kind of projects do you want to work on? What kind of clients do you want to work with?

This is where you decide if you want to be a generalist or a specialist. Will you niche yourself into working in certain industries only? Or will you take any project that comes your way?

Another thought that normally doesn’t come up until you’ve been freelancing for a long time, but is certainly viable for a newcomer, is whether you’ll want any clients at all. If you’ve got the skills you can create as many businesses and products as you’d like and you may never even need to have clients.

6.  Are You Planning to Work Locally?

If you’re planning to have local clients, you’ll need to market differently than what you’d do if you’re planning to work with clients nationally. For local clients, you’ll need to actually get out of the office a lot more to attend local functions and meet with the clients.

If you plan to work nationally, you’ll rely on the internet for your marketing. Concentrate on getting your name in front of as many potential clients as possible.

7. Do You Have a Good Website?

Whether you plan to work locally or nationally, it’s 2011 my friend and you need a website. Nowadays, if a business (no matter what is it) doesn’t have a website, it’s almost like they’re not legit.

Not only is having an actual website important, but it needs to look good. It doesn’t matter if you’re a copywriter, developer, or some kind of freelancer that doesn’t deal with design. People will judge you and your work based on how good your presentation (the design) looks. Just like you wouldn’t go into a job interview or meet a client in shabby clothes, don’t let the first thing your potential clients see be a shoddy site.

8. Do You Have Enough Space to Work?

Where are you going to work as a freelancer? While it’s certainly possible to work off your dining room table or in a closet, I really recommended going with a real office. You need a calm, clean and nicely decorated space where you can close off the rest of the household and think. You need to be able to conduct phone calls, sit in concentrated silence or be able to blast loud music while you’re working.

9. Where Do You Want to Be in Five Years?

Is your long-term plan to remain a freelancer until retirement? Or do you want to run your own agency or hire some employees or make your own products? It’s okay to start at one place now and slowly work your way to another. Just be sure you always work with your end goal in sight. Just like you don’t want to wake up at 60 to realize you’d worked at a place you hated for 40+ years, you don’t want be trapped in a freelancing role you hate.

10. Should You Freelance?

Now for the final question–can you make it as a freelancer? Are you ready? Have you thought this through? While trying to get clients and having savings for the down periods is important, strategy is the most vital planning activity you should invest your time in. Your initial thought processes about freelancing will almost certainly determine whether you’re a success or failure as a freelancer.

Your Thoughts

What are some important questions you think people should ask themselves before they become a freelancer?

Image by bareknuckleyellow

Related posts:

  1. 42 Questions Every Freelancer Should Ask Their Clients
  2. 50 Questions to Ask Yourself after 6 Months of Freelancing
  3. 3 Questions Your Customers Are Dying For You To Ask
  4. Seven Questions to Ask Yourself Before You Outsource
  5. 15 Questions to Ask Before Collaborating

About the author: Amber is a freelancer with over 10 years of experience and specializes in clean, semantic and valid HTML5, CSS3 and Wordpress development. She also writes a web development blog at www.amberweinberg.com and just launched a web app for developers at www.codesnipp.it.



 
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36 Comments
  • User Gravatar
    Nicole Smith
    July 11th, 2011 at 8:48 am

    All very good questions to ask. I myself would love to freelance full-time one day, but if I plan on having kids and building my dream home, the idea of leaving my steady full-time job is scary. I don’t want to make ends barely meet with freelancing. I want to give my kids the life every parents wants to give their children.

    -sigh- Decisions, decisions.

  • User Gravatar
    Amber Weinberg
    July 11th, 2011 at 9:48 am

    @Nicole I wouldn’t equate freelancing with “barely making ends meet”. I actually make about 4x more as a freelancer that I could’ve made at an equivalent full-time job. We’re actually trying to have kids now, and happy to know that when I get pregnant and after I have the baby, I’ll still be able to work and stay at home with the kids…if you really want to start your own business, now is the time to do it before you have so much stuff to take care of. :)

  • User Gravatar
    Nicole Smith
    July 11th, 2011 at 9:56 am

    @Amber – I hope I can make 4x as much freelancing as I do now at my job where I’m a web developer. What motivates me to want to freelance full-time is the fact that I had to take down my website as I’m considered competition at work, and I’ve worked so hard over the years to establish myself with my brand, and it’s hard to get business without a website to showcase my work.

    I also have a car payment tying me down for the next 6 years :P

  • User Gravatar
    Phanor Coll
    July 11th, 2011 at 10:16 am

    great questions, I asked some of those myself, before becoming a freelancer, and it’s paying off.. I’m making more that in my last full-time job, it’s been a great ride..

  • User Gravatar
    Steve
    July 11th, 2011 at 11:07 am

    Great article Amber! These are some great questions to ask when deciding to go fulltime!

  • User Gravatar
    Pavel Byzov
    July 11th, 2011 at 11:37 am

    very good post, question about the money I like especially

  • User Gravatar
    Some Design Blog
    July 11th, 2011 at 12:00 pm

    These are some really good questions, Amber. A couple that I would add for those interested in freelancing would be “Do you have the money management skills to survive slow periods?” and “Are you willing to learn the skills required to effectively run a business?”.

  • User Gravatar
    Gold
    July 11th, 2011 at 12:46 pm

    Are these the same questions you asked yourself before you started freelancing?

    Number 5 brings to mind the unanswered question I’ve always had as to what major when going to college? If one sat around waiting for an answer to that question one would spend their lives collecting and taking to the recyclers plastic bottles and metal cans. Now that’s freelancing!

    Number 9 reminds me of an event I witnessed while going to USC. While sitting in front of the engineering Building a Freshman and Ice Cream Vendor were discussing some future event and the Ice Cream Vendor was telling the Freshman about his plans for a future event that he was planing. The Ice cream Vendor was going to have a band and troupe of dancers follow him, in his casket, being drawn by a team of six white horses down the street by the USC. The Freshman exclaimed that he should talk or think about things like that. The Ice Cream Vendor replied, “I’m 95 years old. What else should I be thinking about?”

  • User Gravatar
    ioana
    July 11th, 2011 at 1:14 pm

    I completely agree with Amber on the money part (and of course the possibility of working from home). I’m just going into full-time freelancing myself and one the main reasons is that I’ll earn at least 2 times more than what I’ve been earning as an in-house SEO. I can make 500 dollars per week! One just has to save a lot of money when business is good, to make sure they’ll be fine even if there’s a dry period later.

  • User Gravatar
    Scott Lassiter
    July 11th, 2011 at 4:40 pm

    Really good post and I answered YES to most. The problem is the money. I have a “Cushy” yet “stressy” job, however it pays well and puts the food on the table. Also, it is sustaining and I do not necessarily have to find work, where if I was a freelancer I would always be on the lookout. I think I have the skills the talent and drive, however I just don’t think I would be smart to leave where I am for the uncertainty of the full time freelancer. You seem to do well, what is your secret?

  • User Gravatar
    Daniel Lopez
    July 11th, 2011 at 5:17 pm

    Solid article but being a freelancer, I believe needs to be experienced. Planning only takes you so far. You never really know if you are as motivated or as skilled as you think you are until your forced to sink or swim.

    My problem has always been being motivated to work. No matter whether you freelance or work full-time you’re still putting in 8 hours like the rest of the world. The difference is you can adjust your hours as needed but for the most part there isn’t much flexibility as some make it out to be. I went in thinking I could work less and still make enough to survive but that isn’t an option when living in a major city. It was naive but I was hoping to escape the boredom of a 9-5 and instead I was introduced to the boredom 12-8. Others I’ve heard have it even worse working insane overtime. But a lot of that comes down to project management.

    Also, in terms of making more money – it’s definitely possible and some folks can make a much better living freelancing versus full time. As a designer, I found this to be a bit more difficult as nobody wants to hire a designer on an hourly basis because the whole process is so subjective and harder to quantify. As a freelancer, I fail time and time again to make sure I stick to the hours allotted. It’s a challenge to say the least.

    But in no way do I not regret giving it a go :) At least now I’m more aware of what it takes to make this work.

  • User Gravatar
    Amber Weinberg
    July 11th, 2011 at 9:07 pm

    @Scott The “secret” is not to think about the money…worrying about making enough just stops you from getting out there and becoming successful. And PS…a full-time job is actually less secure than you think. You have no control over keeping your job, whereas in freelancing, you can control everything,

  • User Gravatar
    Mathy
    July 11th, 2011 at 9:55 pm

    I have been looking to ask questions about freelancing. After loosing my job I haven’t been able to find work and decided to play with various project ideas. One of which I am more consistent with that is storytelling and my blog.

    I have incredible motivation but for me it’s more about having a balanced work day when freelancing. I can work on my own and because I know there’s no one else to do the work I push extra hard. Which is why I am able to understand when I have over done it.

    It usually manifest by me not wanting to do any work that’s when I know I need to do something totally different to have a break.

    But I am desperate to know if you can recommend different ways to maintain healthy work balance and focus.

    I appreciate your time

  • User Gravatar
    TLC
    July 11th, 2011 at 11:37 pm

    Question 11 should be, “Do you like roller coaster rides?” Because the hardest part of this for me is riding the roller coasters of ever-varying work and income. It’s really scary when you’re a single parent and have no backup income or support. Fortunately, I have a very supportive 16-year-old son who won’t let me quit! Without him, and my faith, I think I would have chickened out a long time ago.

  • User Gravatar
    Marcus Lewis
    July 12th, 2011 at 12:07 pm

    @ Amber – Great article!

    The control is what I love about freelancing and the possibilities are endless. I’ve never liked the idea of working a full-time 9-5 job. I’ve always wanted to be my own boss, so straight out of collage I jumped right into freelancing .

    @Daniel – It’s not about the hours you put in, it’s about what you do in those hours that really matter. When becoming a freelancer, in my opinion, one shouldn’t restrict themselves to 40 hour weeks. Freelancing is a world within itself and needs to be attacked differently.

    I didn’t have the same skill set back than that I do now, but I knew I had what it takes to learn everyday and become successful. I’m still working towards my goals and reading this article, still being happy with the decision I made is a great feeling. I now mainly focus on web design and am currently on track to make about twice as much as I did last year and I’m not stopping.

    I love freelancing even though some months are worse than others I know some day soon I wont have to worry about that.

  • User Gravatar
    Daquan Wright
    July 12th, 2011 at 1:34 pm

    Good questions, all of them. Personally, my top questions would be “Can you sell yourself?” and “Do you have the drive and passion to learn the management skills necessary to freelance?”

    Even though my intention is to work a full-time job (with software), I am going to be a part-time freelancer in the areas I like.

    The sell yourself questions is about marketing yourself, connecting with people, and portraying your website the way you want it to be scene. Your website is your main marketing tool (aside from testimonials/referrals, which I find to be even more important). If you got a website, people at least know what you’re about by looking at a few pages. You have to be willing to put yourself out there and show your knowledge. You’ll always have to sell yourself, regardless of whether you freelance or not.

    The management question is broad, but relates to money management, project management, time management, and hitting deadlines. I think if you can do both of those, you can do full-time freelancing in my opinion.

    For all the freedom you get, you have to be independent in every aspect. A regular job is steady, but like a jail, there are restraints in every aspect of the job. When you work, how you work, who you work with, etc. A regular job is for people who like to be managed and don’t want to deal with the business side of things.

    I’d prefer both, so thus my long term goal. I want a job in what I’m majoring in (CS) and I’ll get nice benefits. The part-time freelancing gives me time to pursue projects I dig, learn technology I’m passionate about, and learn some aspects of business. If I ever decide to full-time freelance, I will have acquired the knowledge to do so in the future (though that’s not my goal).

    In technical details, I can easily sum up what you need to freelance: quality of work delivered and work delivered on time, as Amber said. :)

    You need vision to brand your own business and you must really want it to work. Otherwise you will have given up when things don’t go your way.

    A steady job is secure in terms of managing most aspects of the business for you. But a steady job might give you a steady check, but anytime they need to make cuts, you have to realize they have 100% control of it and you do not.

  • User Gravatar
    Alex
    July 12th, 2011 at 2:46 pm

    The key to succeeding as a freelancer is being consistently good at what you do and maintaining high quality. Unlike being on the payroll, being mediocre just isn’t good enough because there is no-one around who will pick up the slack.

    I agree that you shouldn’t really think about the money you’re making. Concentrate on the quality and the money will come.

  • User Gravatar
    Scott
    July 12th, 2011 at 2:52 pm

    @Amber
    Amen I hear ya! One thing I despise about work is that I am in no control of what I am tasked to do and I cannot stop working with a client if they are too tough to work with. The paycheck is nice, and the wife is happy, however with cuts, a bad economy, and a weird work dynamic, things are just uncertain. I do about 5% freelance now in comparison to my full time job and I love it, other than having to use the extra time. I feel like I am actually contributing to something worthwhile, other than someone elses’ agenda. The trick is to bridge the gap and not go into a huge debt doing it! Also, I have heard that you need to put in a LOT more time and I have a pretty good schedule now, however I love the idea of not exceeding PTO or having a limited salary. Thanks for the positive feedback and good luck! PS, kids are wonderful and make such a difference in life, especially when they are begging to play with your design and paint applications:)

  • User Gravatar
    Nikhil Malhotra
    July 12th, 2011 at 3:22 pm

    I work in a company and side by side I do my freelance work. I started doing these two things together almost a year back but with time I have realized that freelancing is a very hard thing as you need to do everything alone especially in the beginning when one does not have many contacts.

    Are you motivated enough to work alone and handle all the responsibilities?

    That’s another question which everyone should ask themselves before jumping on the path of freelancing.

  • User Gravatar
    Warren Laidler
    July 12th, 2011 at 5:12 pm

    Great article Amber! Thanks for the insight. I’ve been freelancing for some years now and though it’s not always a smooth ride financially, It’s been very rewarding. There’s nothing like being your own boss, setting your own hours and providing quality services. You made some very good points regarding preparation, things that I also considered before going off the beaten path myself. Thanks again and good luck to all the future and current freelancers out there, Power to the people!! lol.

  • User Gravatar
    Peleo
    July 13th, 2011 at 11:39 am

    What if you have no better choice? You’re in your 40′s and can’t find a decent full time job and you’ve been out of work for over a year. Most of these questions don’t apply since it’s not a real choice. Yet, you need to make it happen. Any chance to succeed or you’re destined to fail?

  • User Gravatar
    Amber Weinberg
    July 13th, 2011 at 11:45 am

    @Peleo of course you have a chance to succeed….get working!

  • User Gravatar
    Alex
    July 16th, 2011 at 12:41 pm

    @Peleo that’s often the best motivation :)

  • User Gravatar
    Paula
    July 17th, 2011 at 4:08 pm

    Great article. I have found most of those to be true.

    But I would add one more: The ability to say no. Being disciplined enough to ignore my house and kids and get my work done AND gently remind people that even though I set my own hours I still have to get work done.

  • User Gravatar
    Julien CROUZET
    July 18th, 2011 at 10:16 am

    There’s one point missing : Do you have some backup money ?
    Freelancing is a very random work, you could be without income one or two months !

  • User Gravatar
    Marcus Lewis
    July 18th, 2011 at 10:22 am

    @Julien, if your looking through the right resources and are persistent in marketing your freelance business you’ll definitely have income each month.

  • User Gravatar
    Shaleen Shah
    July 19th, 2011 at 4:45 am

    If I were to add item #11, it would be: Do you have passion in what you do? I think that anyone can be good at any freelancing niche, but to be successful and great, you have to be passionate in what you do. Now, I wonder why a lot of people think that freelancers are a lonely bunch. Just because you’re working solo doesn’t mean you are not happy with your choice of work…

  • User Gravatar
    Marcus Lewis
    July 19th, 2011 at 10:22 am

    @Shaleen, I 100% agree with you! Passion and determination will definitely help you success no matter what career path you choose.

  • User Gravatar
    Daquan Wright
    July 19th, 2011 at 11:05 am

    I’ve read that to keep a hold of your money, it’s good to save most of it and give yourself and allotment every week. So say, if you pull in 3k a month, you could give yourself $400 a week and put the rest away. I think for some people, it would be a worthwhile technique.

    For me, passion and drive are key as well.

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