3 Years of Freelancing Full-Time: What Have Been The Biggest Surprises?

My friend Melanie asked me at happy hour tonight what I thought the biggest surprises of freelancing were for me. It’s an interesting question to think about. And to be honest, it’s a little hard to remember back to when I wasn’t freelancing.

But I know I’ve had a few good ideas all along. So if you’re thinking about freelancing full-time, here are some things I learned that may help you.

It takes a while to get started

I planned about 8 months ahead of time to quit my job and go freelance full-time. And yet I thought once I started, I’d be booked solid in no time. But that wasn’t the case.

I quickly realized one key thing: I had no idea how to get clients. Sure, I had found some clients that came my way organically. But that was through networking and other long-term means. Finding clients when I needed them wasn’t something I had done before, and it took months to get a system going.

Thank goodness for my $8,000 quit my job fund.

Marketing yourself is a long-term strategy

Going along with the point above, I realized after a while that I could get clients without even trying. And they’d come from the strangest places!

One found and hired me because I had worked for a competitor of theirs in the past, and they noticed this on LinkedIn.

The weirdest referral: a client found me in a testimonial I had left on a site completely unrelated to personal finance. And the kicker: I didn’t even mention I was a freelance writer in the testimonial!

This was an important lesson. Being everywhere does count. You just might not see the results right away.

I hate working at home in my pajamas

This one has turned out to be the biggest myth for me. When I quit my job, I was like “Great! No more commuting in to an office! I’m just going to stay at home and work in my pajamas!” Damn did that get old fast!

Instead, I found myself getting really bored and lonely. I also wasn’t very productive since working out of my apartment (that I shared with roommates) didn’t leave me much space for a dedicated workspace.

About 6 months in I joined a coworking space, and I’ve been commuting to an office for my freelance work ever since.

Working on a schedule (like 9-5) actually makes the most sense

Another thing I thought I would love before I quit my job: flexible scheduling. I would just work when I felt like it. Nights, weekends, whenever. I wasn’t doing the 9-5 thing anymore, that was for sure!

But again, this just wasn’t great for productivity. Instead, I’d get more stressed, especially without clear boundaries between work and free time. I soon found that having some sort of work time scheduled was best. And what’s worked best has resembled a 9-5, M-F schedule or something similar.

However, I do take time off when I need it and wouldn’t be able to do at a normal full-time job. I’ll roll into my office at 9:30 am if my workout runs late. And unless I have something super urgent to do, I’ll take Friday afternoons off. Don’t get me wrong, I love this part of freelancing. But I do need some structure to work within.

Do you freelance? What’s been most surprising for you?

The Next Chapter…

As you may have noticed, Money Spruce hasn’t seen many updates lately. After quitting my job in May 2012 and becoming a full-time freelancer, there’s just been less and less time to write on here.

Today, I’m announcing the launch of my new business: Content Strategy for Do-Gooders.

CWAM is a one-stop shop for content strategy and creation for social mission-driven businesses and organizations. CWAM’s focus is to help these businesses amplify their social impact using effective content to tell their story, find more followers, and develop a loyal tribe of supporters.

Why am I making this change? There are a few reasons:

1. Social missions have always been close to my heart. After finishing my master’s degree, I passed up jobs with starting salaries of $60,000+ to work as an AmeriCorps VISTA volunteer. I served at a nonprofit in New Haven, Connecticut for a year, living on a stipend of  $1,100 a month and supplementing my earnings with food stamps. I learned so much that year as I lived closer to poverty than I ever had before.

After, I was hired as a full-time employee at the same nonprofit and continued to work there. I focused on helping my nonprofit update newsletters, refresh content, and simply do more to leverage online content to bring in more donations and stay in touch with past donors.

2. I’ve become much more than just a “freelance writer.” While writing is still a large part about what I do, it’s still just a piece to the much bigger puzzle of developing a strategy that works for the organizations I serve. In addition to writing, I spend hours strategically deciding what kind of content to develop and incorporating that into a larger content strategy. This strategy includes effective call to actions, email capture, lead nurturing through email, social media, blog posts, static content, and more.

3. Socially-minded businesses are perfectly suited to gain the most from an effective content strategy. Effective content is really about telling a great story. While many brands do a good job telling a story, fewer are actually “story-doers,” to use a term from this article published in the Harvard Business Review. Preliminary research from this study shoes that story-doers may be much more effective businesses than story tellers.

Social businesses like TOMS Shoes and many great others have amazing stories to tell. It’s these stories that earn them a large following of supporters. Supporters are really more than customers. They’re brand advocates who want to make a difference in the world, too.

My BIG goal: help more businesses and organizations harness their own powerful stories to gain more followers and increase the impact of their mission.

Thank you

Thanks so much for following along on Money Spruce. My life would be incredibly different right now if I didn’t start this blog and hear from all you loyal readers.

If you’re still hungry for more personal finance and other money-related articles, my friends Carrie, Mr. Money Mustache, Paula (and many more) are among my favorites to read for a steady stream of interesting and informative posts.

Wishing you all the best and brightest future,


P.s. – If you or anyone you know may be interested in my services,  I’d be really grateful if you’d send them over to this page. Here they’ll be able to get my free report “10 Steps to Maximizing Your Cause’s Impact with Content.” Thanks again for all your support!

Thinking of Quitting? Self-Employed Lessons, 2 Months Deep

That first two months after (finally) quitting my job definitely flew by! I’ve had a successful move from New Haven, CT to Portland, OR! Life has been memorable in a gazillion ways, and the fun is just getting started.

Today I bring to you lessons I’ve already learned and that you’ll need to watch out for or can look forward to for yourself.

Self-Employed = Awesome!

So far, 99% of the time has been freakin’ fantastic. You’re probably thinking I’m exaggerating, but I can honestly say I couldn’t be happier with life right now, and I’m committed to doing every possible to keeping it that way.

I’ve gotten to meet a ton of new people out here in Portland, and not having a job to hold me back has definitely helped that. Friday afternoon Dark Knight Returns showing? Sure! Sunday bar crawl? Why not?

It’s possible that I’m still in the post-job haze, but I’m just eating it all up for now until my feelings tell me otherwise.

Having Some Income is Better Than None

Initially, I was going to make the jump from my steady income from job to zero income at all. I planned to save all along, and I ended up with about $7,000, strictly for making the transition to self-employment. But, a few weeks before getting my job, I came across a position that fit in nicely, allowing me to write freelance part-time and still be able to work on projects that I wanted and do other things that I just love to do.

While it would be nice to be 100% free to do whatever I please, having a small income that still covers most of my living expenses has been a huge relief. It’s expanded my time horizon for when I’ll run out of money if my other endeavors don’t bring in cash as soon as I hope. Right now I’m looking at least 6 months of expenses in the bank, so I’m not concerned for that any time soon.

So, I’d recommend: Unless you have solid financial backup, consider being a part-time quitter. This can even work if you don’t have much savings at all but desperately want to leave your job. Freelancing is always an option, but there are some decent part-time options, even some that offer health insurance.

Don’t Forget New Expenses

Speaking of health insurance, you’re going to need to pick up coverage for yourself and potentially your family. I went with eHealthInsurance, and I found a decent plan for about $100 a month. Yes, it’s pretty bare bones with a $5k deductible, but it’s not much worse than what my previous employer offered. Plus, I’m young and happily healthy 🙂

Also, once you have self-employed income, you have to remember to set aside money for taxes. For now, I save 30% which is hopefully a conservative amount ( and I’m overdue to meet with an accountant!)

Advice to ya: Don’t forget to factor these things into your budget before you leave your job, like health insurance and additional taxes, to get a more realistic picture for what your monthly expenses will be like.

You’re Probably Going to Freak Out At Times

I’d be lying if I said that I haven’t doubted myself already. I know it’s early, and I have momentum going for me, but the long-term path still isn’t clear and likely won’t be for some time. I’ve had a few moments of agony, for sure, although none of them had me regretting that I quit my job.

For me, the biggest tool for taking on this one has been positive thinking. It may sound silly, but I’ve gotten amazing relief telling myself “I am awesome, I can do this, and I refuse to fail.”

According to a recent talk I attended at WDS by Brené Brown, it’s our psychological inclination to believe that when things feel good, they can’t last and we wonder “Okay, I feel great, but what’s going to go wrong here? Something has to.” Thinking like that is total bullsh*t, and I’ve been doing all I can to fight any of those feelings and keep being happy.

Do this: Do your best to stay level-headed. It’s okay to use some discomfort to push you forward, but freaking out isn’t going to help you be productive.

Find a Routine as Quickly As You Can

I remember always sitting at my desk job and thinking something like “If I can just get out of here, I can easily add 40 productive hours a week to my freelance work, blogging, and other projects! I’m gonna be banging out blog posts like a boss!”

Fast forward two months: It hasn’t quite been the productive paradise that I imagined. 

Month One (June), I was pretty committed to doing the bare minimum and chilling out (had to catch up on How I Met Your Mother somehow, right?).

July, which was almost entirely in Portland, has gotten better work-wise. It hasn’t been perfect by any means, but I’m slowly discovering how and where I can be most productive.

I’ve finally put the tools from Zen to Done (a simpler version of Getting Things Done) to work to organize my weekly and daily tasks to be more productive. Creating systems has definitely been a key for me, and I think it will set you up for success much better than just randomly trying to conquer your work.

For you: Whatever you need to do to get in the working groove, find it as soon as you can.

Diversify Your Income, and Don’t Work for Peanuts

I already had one slight scare that I’d lost all my freelancing income. It was a terrifying moment (and luckily it was just a quick one), but I’m determined not to wait around for it to happen for real.

You, too, should be thinking about how you can earn your income from more than one source. To say the very least, it’s reassuring to know that your entire well-being doesn’t rely on a single job.

While you’re at it, don’t get desperate and devalue your time and your work. Sure, I’m looking for more freelance work, but I’m not going to jump at just anything, especially if it pays less than my time is worth. I’ve turned down a few opportunities already because of this. I’m not greedy by any means, but I’m not going to work for minimum wage, either.

Have questions about being self-employed? Or is something standing in your way? Let me hear it in the comments!

Note: This post does contain affiliate links, and I will earn a commission if you click on and buy from those. But hey, I recommend these products, and I appreciate your support! 

I Did It! I QUIT My JOB!

This is the post of I’ve been waiting to write and, after 9 months in the making, it’s now official: I quit my job! It feels like a huge relief to finally be done and to move on from New Haven, too.

Why I Quit

There are a few reasons I decided to leave my job:

1) I was bored and unhappy. While my job wasn’t stressful and my boss was great, I was bored at my job. I felt like I wasn’t going anywhere and wasn’t making a difference in the world on a daily basis. I’m sure I could’ve just coasted along for some time, but that’s just not my style or desire.

2) I need to give self-employment a shot. I’ve always been entrepreneurial-minded and I even attended Babson College, the #1 ranked college for entrepreneurial studies, before I decided to transfer out. I’m not sure that I’m born to be an entrepreneur, but I know I need to find out before I’ll ever be content with going back to a desk job. Now is the best chance I’ll ever have in my life to go for it. I’m not scared of failing at this, and even the worst case scenario isn’t bad enough to stop me.

3) I wanted out of New Haven. I moved there with my girlfriend, and she just graduated from Yale. Neither of us planned to stay after she finished school. I had a great time there and enjoyed the people I met, but New Haven just isn’t the place for me right now.

How It Went Down

I’d love to excite you with a dramatic story with how I quit my job, but there isn’t one. This is totally fine since things were’t emotional and there was no animosity whatsoever from my boss or coworkers. I left completely on my own terms. My boss actually knew way in advance that I’d be leaving May 2012, and I gave her official notice of my last day about a month ahead of time.

On May 25th, I walked out the door for the last time and never looked back.

The Money Question

As you may have guessed, how I’ll earn money to continue living is one of my largest concerns, and one that many others ask about, too.

Remember my Quit My Job Fund? I saved $7,000 in that. It’s a little less than I hoped, but I kept blog and freelancing income separate and haven’t cashed any of that out. I also have other savings to fall back on if I need to.

More importantly, I do have part-time income from both writing and SEO. I’m now staff blogger at HatToss.com, where I write 3 posts a weeks for money issues related to college students and recent grads. It’s a dream topic for me, as I can definitely relate to some of the money highs and lows of the younger crowd.

I’m really enjoying writing right now, and I’m confident that I’ll pick up more clients when the time allows. I’m hoping to eventually have 2-3 more consistent clients so that I can earn a real wage that allows me to save some money, too. This is the path I see myself going down right now, but who knows if that’ll change? It’s exciting to think of the possibilities out there for me now, and I certainly don’t want to rule any of them out.

In all honestly, I haven’t been looking around at all yet since I planned to take this time of transition slowly. I currently work about 15 hours a week with a flexible schedule and work that I can do from anywhere with internet. For summer, that makes me happy.

In a couple weeks, I’ll be moving out to Portland, Oregon for the summer. Once there, I’ll attend the World Domination Summit in Portland in July as well as the Financial Bloggers Conference in Denver in September (looking forward to seeing all my friends there!). I’m excited to explore the Pacific Northwest a bit while I’m taking it easy on the money making side.

Shoutouts to My Favorite Quitters

I just want to say “thanks” my favorite Quitters and to those who have supported me and helped me along the way.

First and foremost, I have to thank Sean Ogle for putting this whole idea in my head. A year ago I would’ve had no idea how to make this leap. But through Sean’s Location Rebel course as well as inspiration from Sean’s blog have helped answer some of the questions and overcome just about any fear that I’ve had.

I also want to thank Caleb from Pocket Changed for his support along the way. We had some fun plotting this date months ago.

Tom at Leaving Work Behind has had some awesome advice, and I actually got my first freelance writing job thanks to a link in one of his posts!

I also think back to reading some posts from Tyler at Advanced Riskology and Jenny at Life After College about their journeys.

Of course, everyone at Yakezie has been huge along the way, too.

My family and friends have been fantastic in supporting me. I feel blessed that everyone trusts in what I’m doing and has offered encouragement along the way.

Thanks to everyone else I forgot to mention (you know who you are!). Even if it’s just been a short comment or blog post you’ve written and I’ve read, it’s been a part of this amazing journey for me.

Final Lessons

I’m not writing this to prove a point or rub it in anyone’s face. I don’t think jobs are stupid (and I wouldn’t rule out going back to one myself). Besides, my life problems are far from solved, and I know I have some big challenges ahead.

The one thing I will challenge everyone reading this post to do is to change whatever it is in your life that’s making you unhappy. There are always options out there. They might not be easy at first, but you have to take action.

I look forward to sharing more with you on here as the next few months progress. You can follow me on Twitter to get all the updates not only on Money Spruce but my work in other places, too.

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Life After Quitting – A Few Quick Updates

I know it’s been a few weeks since I’ve given any updates, but I’m working on a big post about quitting my job (which I did 2 weeks ago). Look for it soon.

In the meantime, I’ve also been writing weekly for Hat Toss, a site with money, career, and health tips for college students and grads. Here are a few of my recent posts up there. I’d love it if you’d stop by and Like or Tweet the posts:

Your First Paycheck! What to Do Before Spending It – Just as it sounds, this post has advice for what to do when you get your first big paycheck from your first job after college. As you can guess, I don’t propose spending it all on gadgets 🙂

5 Ways to Travel on a Budget – As you know, I try to travel as much as I can (even though I don’t have a ton of money to do it). Here’s some of my best tips for traveling, especially for recent graduates that might be faced with the tough decision of traveling and going into credit card debt to do it.

That’s it for now. Thanks for stopping by!

How to Quit Your Job and Love What You Do Next

I’ve been in a bit of a panic lately. I’m only a month away from quitting my job and losing my full-time income.

But while scrambling frantically to replace my full-time income, I came across this great post on Live Your Legend that’s on how to quit your job. To summarize the whole post, the takeaway: do NOTHING immediately after quitting or getting fired. At least for three weeks, according to Scott Dinsmore.

Now, I hadn’t thought about this too much before reading this post. I’d been focused on trying to replace my income right away by taking on more work, which I’m not sure I’d be too happy doing. While I do have thousands in the bank in my quit my job fund, I know I can’t wait until this runs out to bring my income up.

But after reading Scott’s post, why should I just be trying to just go out and make money immediately?

Here are some things to think about before scrambling to replace your income after quitting or losing your job.

Give yourself a break

If you quit because you disliked your job, you need a break. I think the three week period suggested is dead-on. Most of us aren’t going be in financial ruin because of a three week gap.

Instead, plan a retreat or vacation. Scott points out many things you could do, like travel, a meditation retreat, or just start writing. Consider this time a time for inflection. Figure out what you’re really interested in and then decide where you can go next.

Don’t forget to make every day count. It’s easy to be miserable when you have no job and no income. Your life might temporarily feel like it has less purpose and meaning. Even if you feel this way, don’t waste your time sitting on the couch. Do what interests you and what you always hoped you could do if you didn’t have to work a job.

Seriously consider a change

If you hate what you do, why take another job that you might hate? This entirely defeats the purpose of quitting in the first place. Instead, be sure to relax and think it over a bit before immediately jumping into something else. Don’t jump back into the same type of job unless something comes along you can’t pass up because you’re genuinely excited about it (and not just the money or perceived opportunity).

I’ve already been tempted to seek out a full-time job. The money would be awesome and would make the transition easier. But, after stepping back, I’ve decided that I’m not just going to take any job that comes my way.

Don’t act on emotion

I wrote about emotions and money in a post last week, and it’s important to assess that in this case, too. The money isn’t what’s going to make you happy. It’s what you’re doing with your life that will ultimately have the greatest effect.

Be as level-headed as possible about making any important decisions. Don’t just take a job because you feel you desperately need the money or because you’re unhappy being unemployed. Do all you can to ensure the job will make your life better than it is now or was before.

Turn misfortune into opportunity

Remember, changing jobs is a life-changing opportunity. Definitely don’t panic; your life isn’t over.

Pat Flynn famously turned the loss of his job into a remarkable online business. What if Pat went out and grabbed another job right after being laid off? His life would be 100% different. Be sure to think of it as an opportunity and not a loss.

How I’ll quit my job

So what am I going to do? If you’ve read my past post on taking time between jobs, you probably already know it’s something that’s important to me.

For starters, I’ll be traveling around much of the summer. It’s looking like I’ll be hitting the beaches of New England throughout June. I’m then heading to check out Portland, Oregon (a dream for me!) in July for the World Domination Summit. I’m then planning to stay out West until the Financial Bloggers Conference in Dever in September.

Now, I won’t be taking 100% of a vacation during this time, but I definitely won’t be desperately searching for a job this whole time, either. I’ll be working on growing the Money Spruce business, which includes this blog, SEO consulting, and freelance writing. But I’ll be able to work from wherever I choose, which I’m super excited about 🙂

What advice do you have after losing a job or quitting?

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photo by: Gary Brownell

Life After Quitting Questions Answered: Saving, Business-Building and More

There are SO many questions (both in real life and from online people) that are swirling about what the heck I’m gonna do once I quit my job in New Haven. It’s about 2 months from go-time, so things are getting real. A lot of people are curious what I’m doing next. I hope this post answers some of that.

While I’m sure no two people would approach things the same way, I hope this gives you some idea of the types of things you need to think about, too.

Why are you quitting your job?

The simple answer is that my girlfriend is finishing grad school at Yale in May, and we’re both itching to get out of New Haven. Even if we wanted to stay, there’s pretty limited opportunity for jobs. New Haven is an alright place, but I wouldn’t really recommend it as a place to live if you have the choice of anywhere.

Are you going to get another job?

If the right opportunity comes along, I’ll definitely jump on it.  In case it doesn’t, I’ve saved almost half of my income from my job every month for several months now so that I can have savings to live off for several months. I estimate that I have about 5-6 months of living expenses (assuming no income) earmarked for this life change. At the same time, I have some income and I’ll be working to increase how much I make.

If you’re not getting a job, how will you make money?

I’ll be honest: I don’t have that entirely figured out yet. My SEO consulting is starting to gain more traction (got a new client last week), but it’s still not close to replacing my full-time job income. I do earn some money from this blog, and I’ve dabbled in freelance writing as well. I’d certainly consider working in a part-time capacity for someone if it allows me to both learn and stay location independent.

This whole thing sounds scary! Aren’t you afraid?

Honestly, not so much. I subscribe to the “what’s the worst that can happen?” mentality in cases like these. I don’t see too many awful scenarios that are realistic. I could go broke, but I doubt I’ll end up homeless or starving. I could move in with family or friends if I got really desperate (although I’d have to be pretty desperate for that to happen).

Being broke at 26 years old isn’t the worst position to be in (and many Americans are already far, far worse off). I’m not saying I want that to happen, but I’m not afraid if it does.

How will you make a down payment on a house?

Hah! Sorry to laugh, but I don’t plan to buy a house for some time. Here’t the short list why:

  1. I have no idea where I want to settle down yet
  2. I value mobility.
  3. I have no desire to have a mortgage payment
  4. I like the life of a renter and not having to worry about random surprise costs like repairs.
I wouldn’t be surprised if a lot of people my age don’t plan to buy. In fact, a recent survey showed that only 7 percent of respondents thought owning a home is an important part of the American dream! Times are a-changin!

What about health insurance?

I haven’t chosen a plan yet, but I’ll probably opt for a high-deductible plan. Based on some quick research and recommendations, it will cost around $200 a month. I’m sure there’s almost no benefits to this type of plan unless I’m severely sick or injured, but are there many more affordable choices in America? Healthcare kinda sucks in the U.S. Aside from that, I have no health problems, and I only rarely visit the doctor.

I thought about COBRA from my current employer, but I’m guessing it will be too expensive for it to be worthwhile. I’ll be sure to check on what the cost would be for me before turning it down.

How will you save for a wedding?

This is the total cop-out answer, but I still hate the idea of spending $20,000 on a wedding. Realistically speaking, it doesn’t look like I’ll be able to afford anything close to that anytime soon. A fancy wedding just isn’t one of my priorities right now.

How are you planning to invest for retirement?

I’m not, for right now at least. I outlined how I’m not investing in the stock market right now (although I did max out my Roth IRA for 2011 if that calms your nerves a little). I’d like to continue to make at least some sort of regular contribution for retirement, but I have to put that temporarily on the backburner. I’ll revisit this once I’m earning some sort of a livable income and not relying primarily on savings.

Where will you live?

I’m not sure yet. There are many options on the table, like NYC or Portland. My fantasy is to be a little bit of a nomad (that’s the whole point of this location independent thing for me, after all). It will almost certainly be a large city that isn’t San Francisco. Ideally it would be ultra bike-friendly.

Do you have any clue what you’re doing?!? Sounds like you’re ruining your life!

I appreciate your concern, but no, I can’t say I have a well-laid out plan for myself. But I’m okay with that. While I am a planner at heart, I enjoy changing things up and not having life be so predictable.

Do you have any more questions for me? Just about anything is fair game, and I’m happy to answer 🙂
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photo by: Steve-h