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The Pros & Cons of Freelancing


The Pros & Cons of Freelancing

by Kate Vandeveld

As you may know, the freelance economy is booming these days, with freelancers set to outnumber full-time employees by 2020.

As freelancers ourselves, many of us hear the same question from our networks over and over again: “Do you think I should try it?” The answer might seem simple to other freelancers (yes!), but the truth is…freelancing is not for everyone.

Pros & Cons of Freelancing - via WhyWhisper Collective

As with almost everything, freelancing has its pros and cons. Since we’re familiar with both sides of the story, we’re happy to share our thoughts on the subject. Let’s start with some of the benefits:

All Kinds of Freedom

This one tops the list. With freelancing comes freedom of all kinds. Freelancers have the freedom to create their own schedules, so they can choose to work at the times of day when they’re most effective, rather than forcing themselves to work at pre-determined times. They can go for a walk on a beautiful day, grab a long lunch with a friend, or just take a break when they aren’t feeling particularly productive. When you freelance, not only do you get to choose when you work, but where you work as well. Are you more productive at home? Go for it. Need to be around others? Try a co-working space or a coffee shop. You can develop your own routine, or opt to mix it up. Plus, as a freelancer, you aren’t confined to a limited number of vacation days. Most of the time, freelancers can work from anywhere with a Wifi connection, so you can travel anywhere without disrupting your workflow.

Perhaps even more important than choosing when and where you work is choosing who you work with and for. At WhyWhisper, we prioritize working with the right people and organizations. We choose to work with individuals who are kind, collaborative, and passionate above all else, and with businesses and organizations that are making a positive impact on society. Before setting out on your own, define the types of people, companies, and organizations with whom you feel you would work well.


Uninhibited Growth

As a freelancer, you have the opportunity to grow your career in whatever direction you desire, creating your own opportunities for advancement. In a corporate environment, your career development is often bound by internal structure and protocol. Though you can advocate for a promotion or more responsibility, it’s not always in your control. When you work for yourself, you can choose how much you want to take on and decide how much you want to charge for your services. It’s not always this simple, but generally, the more you put into your work, the more you can get out of it. 

Speaking of rates, freelancers also tend to make more than salaried employees, on average. In fact, the average freelancer makes 45% more than the average full-time employee. Of course, this depends entirely on your skill-set, experience, and the number of projects you are able to take on, and it doesn’t account for benefits, but the possibility of making more is there. 



When you work eight or more hours each day, one of the hardest things to achieve is balance. You’re working on someone else’s schedule, so it can be difficult to incorporate the things that keep you happy and healthy. Because employee satisfaction has such a strong correlation with productivity, many companies have worked to develop corporate wellness programs in recent years. But when you work for yourself, you don’t need corporate wellness programs – you can do yoga at 10am when classes aren’t full, or wake up and go for a jog on a nice morning. When you’re a freelancer, you have the ability to determine what work-life balance means to you, and develop a schedule that achieves it.

Pros & Cons of Freelancing -- via WhyWhisper Collective


Now, let’s take a look at some of the drawbacks, as we see them:


Most would say that one of the biggest cons of freelancing is the lack of reliable cash flow. When your projects vary month-to-month, so does your income, which can be difficult to manage for some, especially at the beginning.

This means that, as a freelancer, you almost always have to be making moves and selling your skillset. It can be fun – you learn a lot, and have the opportunity to meet cool people almost every day, if you’re lucky. But sometimes, it can be exhausting. As a freelancer, you’re a salesperson, and what you’re selling is your own skills. Making the case for yourself repeatedly can be tough, but as you get more confident in your abilities, you’ll likely find that you’re able to speak to your skillsets more readily and your reputation will spread among your network and beyond, solely by word of mouth recommendations.



Remember when there was someone else being paid to manage your benefits? Someone who filed all of your expense receipts for you? As a freelancer, that person is you. And you don’t get paid extra to do it. While it can be empowering to learn about and manage these administrative tasks, it can also get very overwhelming and/or tedious. We’ve talked about how to set yourself up to manage the administrative side of freelancing more easily so you don’t get stuck with hours of paperwork that you don’t understand all at once. The more you prepare yourself, the easier this aspect is.



As much as the ability to create your own work-life balance can be a pro, it can also be a con in some respects. Because you make your own schedule as a freelancer, you also have to set your own limits. While you’re no longer expected to stay at an office from 9 to 5 (and often beyond) each day, you’re also not restricted to any “normal” working hours. This can make it hard to stop and take a break, or move on from work to do other things. And when you do, it can be difficult to shake the guilty feeling that you should keep going, working on your portfolio or seeking out new clients. If you aren’t able to set boundaries for yourself, you could easily burn out.  

So before you decide to take the leap into freelancing, definitely take the time to think it through carefully. Is your personality one that can handle the ebbs and flows of freelancing? Is the freedom worth the uncertainty that comes along with it? We certainly think so, but we know it’s not for everyone.

What do you think are the biggest pros and cons of working for yourself? Share with us! Here’s how:


The Freelancer’s Guide to 2015


The Freelancer’s Guide to 2015

by Kate Vandeveld

The freelance economy has grown tremendously in recent years. In fact, freelance workers are actually projected to outpace full-time workers by 2020.  And for good reason: Freelancing enables motivated and independent individuals to work for the clients whose missions inspire them, while also allowing organizations to tap into the unique skillsets that they need for particular projects.

But freelancing comes with its own unique challenges, from achieving the optimal client-freelancer relationship to keeping your finances straight. As we have quite a bit of experience in the freelance world, we thought we’d pass along some of our learnings.  Here’s our advice for freelancers who want to kick off 2015 on the right foot:

Maintain a Work-Life Balance

Making your own schedule can be incredibly liberating. As a freelancer, you are often free to work at the times when you are the most effective – early morning, late at night, or somewhere in between. The problem is, without the structure of a 9 to 5 schedule, it can become difficult to step away from work and unplug. There is always more that could be done, whether it’s clocking time on a project, researching potential clients, or honing your personal brand.


But, as with every career path, maintaining a work-life balance is essential for your success (and sanity!). It is so important to “work when you’re working, and not when you’re not.” One way to do it is to set (and adhere to) a schedule for yourself. Whether it’s based on an hourly breakdown or completing certain tasks on a given day, setting goals and limits will give you a sense of accomplishment and give you a clear sense of when it is time to sign off. If you want to do this by choosing a select number of hours to work each day or week, try using time tracking software – it will make your life a lot easier. 


Find a Co-Working Space

In chatting with other freelancers, we’ve heard the same story over and over again: At the beginning of the freelance journey, working from home is awesome. No longer do you have to adhere to a “normal” schedule; you can take breaks when you feel the need, and set up an optimal work environment for you. But after a couple of days or weeks, you may start to feel a little bit isolated or unmotivated. The joy of working from your living room is replaced by a feeling that you need to have a separate workspace, with other like-minded individuals to talk to.


Enter the co-working space. Co-working spaces are offices where individuals work on their own projects in a rented space. If you live in a big city, you’ll find that they are all over the place. Some are catered toward specific niches – tech or creative, for example – while other are open to anyone who needs a space to work. Each co-working space is a bit different, offering different set-ups – from separate offices to open floor plans with desks – and ambiance, so you should definitely do some research and visit the spots that appeal to you before making a decision. Co-working will give you the opportunity to better separate work and home when you need to, and allow you to connect with others who are doing similar or related work.

If co-working isn’t for you, be sure to create a separate spot for working within your own home. And if you want to work outside the home, but can’t find a co-working space, give your local coffee shop or bookstore a try! 


Seek Out Networking Opportunities

As a freelancer, you can secure much-needed support and inspiration by finding opportunities to connect with others who are involved in work that is relevant to your field. Without the built-in relationship-building that comes with working in an office, however, you’ll need to seek out these opportunities on your own.  Even though networking as a freelancer takes a bit more effort, it’s relatively easy to do, and will have a big impact on your career development.

Start by using online forums like to connect with other individuals in your area who are working in your field or freelancing. You can also use LinkedIn as a resource for making connections. Reach out to the people in your network who are working for organizations and businesses that you admire, and ask them to connect you with others in the space. It may seem uncomfortable at first, but more often than not, people are more than willing (and even excited!) to help you make connections with others in their networks.

Co-working spaces often provide networking opportunities as well. Before joining one, be sure to check out whether or not they have events like happy hours and workshops that will allow you to spend some non-working time with the other members. 


Stay on Top of Your Finances


Much of the time, managing finances is a little bit trickier for freelancers than they are for corporate employees. Independent contractors often have to handle their own accounting, from billing to bookkeeping to taxes, and many go into it without knowing the first thing about how to do it the right way. It might sound daunting, but there are ways to make it more manageable. Here are some tips that will make handling your finances easier:

  1. Separate your personal and business finances: This will make your life infinitely easier when tax season comes along.
  2. Select a finance day each month or quarter: Managing your finances all in one annual sitting will likely prove to be quite miserable.
  3. Use accounting apps / software: Find a software (like Freshbooks or Bench) that fits your needs, and take the time to familiarize yourself with how it works and how it can help you.
  4. Set aside a certain percentage of your income for taxes: If you aren’t working with an accountant, you can use a free tax estimator to help you decide how much to set aside for taxes.

When it comes to taxes and planning for retirement, Freelancers Union has some great tools that can help set you up for a successful year – check out their tips.


Don’t Forget About Health insurance

And last, but certainly not least, don’t forget about health insurance. When transitioning to the freelance life, it may be easy to forget about things that were previously built into your benefits package. Luckily, these days, applying for health insurance isn’t as difficult as you might think.

To get coverage, you can apply directly through, which provides a great deal of information on health coverage for the self-employed.  You can also turn to third-party sources like Freelancers Union for information about the best package for you.

However you go about it, just be sure to take care of it as soon as possible – open enrollment now ends on February 15th. If you haven’t applied by then, the only way you can get coverage for 2015 is if you qualify for a Special Enrollment Period. And if you don’t have coverage, you will be penalized at tax time at a rate that is certainly not worth it.


Whether you’re a freelancer or not, the New Year provides us all with an opportunity to start off on a better, more organized foot. Take steps to evaluate your work life, and make changes wherever you can improve.

How do you plan to set yourself up for career success this year? Let us know in the comments below, or connect with us on Facebook, Twitter, or Instagram


Beyond Marketing: Here's What I Really Learned as a Social Entrepreneur


Beyond Marketing: Here's What I Really Learned as a Social Entrepreneur

by Shanley Knox

I joined the WhyWhisper team after four years of work as a social entrepreneur. 

WhyWhisper gives me a place to pass along the lessons I learned in branding a social enterprise. After riding the highs and lows of running a business on my own, WhyWhisper gives me opportunities to work for social change while also being a part of a community. And as a freelancer who, in any given month, can find herself working from East Africa, California, or New York City, WhyWhisper gives me a digital platform to consistently call my home. 

As I work with other companies and causes, I’ve discovered that we share more than the goal of building an impactful brand. We share the often inspiring, but sometimes disparaging, journey along the way. 

So, here are a few things I've learned that have nothing do to with how clickable a campaign will be, but have everything to do with working for social change.

It’s Going to Be Different Than You Think

When I started Nakate Project in Uganda, I thought I would be linking artisans in rural villages to skills training in urban areas, so as to generate local sales. Two years later, I was working to promote female-led Ugandan businesses in international markets. At first, I balked when I saw that change needed to happen. But I began to learn, over time, that the ability to pivot within your business is the only way to effectively find a model that creates impact.  

It’s Going to Take Longer Than You Think

I thought I’d see marked results within a few weeks. I wanted large, measurable impact. If somebody told me it would be years until I began to feel the satisfaction of seeing actual change, I might have quit right then and there. I didn’t want to have to go through the painful building phase where I had to keep seeing the unmet needs of our target population, and feel humbled by my lack of power. What I learned along the way is that systemic change runs a long, painstaking course, and social entrepreneurs experience setbacks, obstacles, discouragement, and failed efforts.  

It’s Going to Be Harder Than You Think

I knew cognitively that pushing social change in Uganda would be hard. I knew it would be long hours, and not a lot of pay, but I didn’t know that it would hurt. I hadn’t yet processed that real change involves the willingness to push through social and societal norms. It means being the odd woman (or man) out. It means saying things that people don’t like to hear, and working to explain why systems should be shifted. Sometimes, it means leaving parts of your business or work behind when it's no longer in line with your vision. All of it is emotional, personal, and often painful. I’ve come to understand that this is part of what makes social change so worthwhile -- good things never come easy. 

You’re Going to Change More Than You Think

I was a different girl when I started Nakate. The business, in itself, has pushed me to my limits. It’s humbled me. It’s exhilarated me. It’s given me a platform to write, to speak, to meet people across the globe, and to discover an entirely new home for myself in East Africa. At some point, I realized that I hardly recognized myself. The experience of living so far out of my comfort zone had pushed me to become someone new. 

It’s Going to Be More Rewarding Than You Think

I wanted to quit Nakate a hundred times on a hundred different days, but I didn’t. And I’m grateful for that, every single day. That’s because my social enterprise didn’t just teach me how to persevere, run a business in a another culture, or afford me the determination and vision to continue pushing through my failures and mistakes. It taught me how to fight for what I love. It taught me to believe in my work, and to have enough humility to change when I discovered it may be faulty. 

Every day I sign in to begin my work for our clients at WhyWhisper, I bring gratitude with me -- gratitude for all that I’ve been taught in my own journey, and gratitude to have found a community at WhyWhisper where I can walk alongside others as they embark on a similar journey. 


Freelance Resources: How to Market Your Skills Without Spending a Dime


Freelance Resources: How to Market Your Skills Without Spending a Dime

The social good network is a tightly knit, passionate community united by shared values, as well as shared goals. As such, it's a space in which a referral or introduction from a trusted source can be the defining factor in landing a partnership or a job. 

Whether you’re looking to expand the reach of your network, establish some credibility, or land a job at a company you care about, here are a few ways to market your skills without spending a dime:  

1. Give Feedback 

Social entrepreneurs and nonprofit founders tend to regularly ask friends and family for feedback and advice. They know that a few key comments on a strategy or campaign can make all the difference in the efficacy of their efforts. As such, offering feedback is a fantastic opportunity to showcase your knowledge and demonstrate your value. 

Looking for a quick and easy way to deliver your comments? Make a voice recording. Tools like EvernoteiPhone’s voice notes or Cloud Recorder  can help you create shareable voice files that succinctly demonstrate your value. After spending a couple minutes on specific feedback points, don't be afraid to throw in a sentence or two about how you might continue to be of service through freelance or contract work. 

2. Co-work

Co-working can be as official as taking part in a program like Goodnik’s in-residence program, or as casual as setting up a weekly coffee date with a friend. The most important thing to remember is that it’s about finding a good working environment for you. At WhyWhisper, we've found that working alongside people who have similar passions and values is what makes co-working most powerful. Why? Brainstorm sessions, problem-solving, and referrals will naturally occur throughout your day.

3. Sit on a Panel 

Social good networks use panels as a way to get to the heart of important issues. Seek out the ones where you can provide the most value while reaching an audience that includes prospective clients and/or partners. Prepare thoughtful and insightful commentary, and pay particular attention to connecting via social channels and email, so as to establish a relationship while you're still top of mind. Your target audience is likely to follow up with additional questions and requests to chat further. 

4. Provide Empowering Environments

Connecting people is a powerful way to demonstrate your willingness to meet the needs of others. In a world of endless meet ups and happy hours, people appreciate introductions that help them to quickly cut through the clutter. Facilitate these meetings by hosting dinners or setting up happy hours with like-minded guests. Your efforts will not go unnoticed, and your guests will be all the more likely to do the same for you in the future.

5. Know Your Own Value 

You have probably already heard that people value those who value themselves. As you establish yourself within the social good community, you will be asked for your input and advice, as well as to lend a helping hand. Carefully providing thoughtful feedback is wonderful. Finding a way to clearly  communicate the monetary value of your product or services is even better. It ensures that others in your network will think of you as a valuable colleague, and opens the door for future business. 

Do you have a helpful tip to share about networking within the social good community? Leave a comment below. We would love to hear from you!