I just got off a great call with Kara of From Frugal to Free who is preparing for her journey into self-employment.

I excitedly told her that quitting my job and working for myself is one of the best things I’ve done. It’s true. What I also told her was that you will never work as hard as you do when you work for yourself and there will be moments when you want to pull out your hair and throw a tantrum because nothing is working.

There are many joys to self-employment, including a flexible schedule and having a theoretically limitless income.

Over the past couple of years, I’ve enjoyed not waking up to an alarm (unless I have a meeting — as a policy, I think alarms are evil), working whenever I want and I’ve also grown my income more than I ever thought possible.

But being your own boss is also freaking hard.

Over the past few weeks with the move and my upcoming vacation, I’ve been working like a fiend so I can take two weeks off and go to Italy with my mom.

I’m currently in one of those “what the eff am I doing with my life” moments and feel like the amount of stress I’m under makes the vacation not even worth it. I know I’ll sing a different tune next week when I’m drinking espresso in Rome, but now it just feels hard and unnecessary. But if I don’t work, I don’t get paid.

And let’s be honest. If you have a full-time job, you are NOT productive for eight hours straight. The same goes for being self-employed, but the difference is I don’t get paid for checking emails and doing something loosely related to work. There’s also a lot of unpaid admin and promotion time. There’s always something to do.

Also, things that use to be “first world problems” like being frustrated when the internet goes out are now big deals. I make my living on the internet and over the past few weeks have been searching for a good connection like a fiend is looking for their next fix.

WHERE IS THE WIFI?!?!?! So I end up at Starbucks. Starbucks is not my first choice, but they have reliable internet so what can I say.

It’s kind of funny because lately, I’ve been that person who brings their whole office to Starbucks. I have my mouse and mousepad, my laptop and just stay there for hours.

Today I’ve already been to two Starbucks in-between a meeting (plus side: last week I worked at a brewery).

There’s also the issue of taxes and healthcare. During a particularly vulnerable moment this week, my accountant called me to discuss the damage for my quarterly taxes.

I almost cried on the phone, but if I’m honest I was crying before he called. My tax bill is not cute. Not one bit. And now I feel broke, right before my trip. Also, I pay a pretty penny for health coverage that in a word, blows.

Back to the crying…when I had a “real job” I was good at “putting on a face” if I was going through some emotional crap. Now that I work for myself I feel all the feelings all the time because I can be myself, by myself.  

While it’s great to not have to put on a social face for others, it really sucks to try to work when you are having a OCD panic attack or after fighting with your boyfriend, or feeling overwhelmed and stressed.

I want to tell my brain “STOP. Now. No, really.” It’s a struggle, especially if you suffer from any sort of depression and anxiety to continue to work when everything is up to you and you have to rely on your own internal motivation.

And let’s not forget about the never-ending impostor syndrome. I still get a rush when I submit articles and feel like, “Will they find me out this time? Will they realize I’m not really a writer and I’m just a good faker who likes to play with words?”

Or the panic/fear that I’ve messed something up. Or missed a mistake. Or that all my clients will leave.

But even after all of this, I wouldn’t change anything. I’m more resilient than ever and through the struggles and fear, I’ve realized that most of my issues stem from me. Nobody else.

As a perfectionist, I put a very high standard on myself, but I realize that I’ve dealt with a number of situations being self-employed and you know what? The world doesn’t end. You move on. And keep going.

Just wanted to share a glimpse into the other side as I think it’s easy for people to think you have it all figured out when you don’t. You’re just doing the best you can. Just like everyone else.

This post is in: freelance, life

You never know where something will lead. I believe this as one of the core tenets of my business and try to treat every opportunity and connection equally.

I know that the best things in life rarely come from constructed opportunities or scripted events. They just happen, in an unlikely place, in an unlikely time.

The path is the road less traveled. The unconventional way. But the chance for making things happen is even greater, because it’s less cluttered.

When I first started this blog, I  couldn’t find a full-time job for the life of me. I tried all the traditional avenues. I applied relentlessly to full-time jobs and kept sending shot after shot in the dark, hoping someone would give me a chance and realize that I wasn’t some sort of loser.

Now that I’m a full-time writer, blogger, and brand connector, I’ve seen how things can shift by trying a new approach. A few examples:

I reached out to Kathleen and she encouraged me to start this blog. I may have never met her as well as a whole other slew of great people in Portland if I didn’t start this blog. I’ve pretty much written for nearly all the local Portland bloggers in some respect and they are all dear friends.

I met one of my business partners on Twitter. We connected over the fact she lives in Brooklyn, where I used to live. I dug her work. That simple connection has now launched a different aspect of my business.

A few months ago in the FinCon Facebook group, there was a post looking for freelance writers. I responded and applied. I got it. They’re now one of my best paying clients.

I got an editing job in another Facebook group I’m in.

I pitched a company in my niche and said I love their content…there was just one problem. There were no female voices. I boldly sent an email and said I’d love to add my voice to the mix. Now I’m a writer for their site.

Last year at FinCon, I met someone for approximately 10 seconds. I was on my way out, but we both joked that we should “network” and exchange cards. So we did and I didn’t think about it that much. But after FinCon, I spent hours sending every single person a unique follow-up email. This 10-second connection in-person turned into one of my largest partnerships.

One of my writing clients saw that I enjoy Twitter and asked me to manage their social media. I happily obliged and got an increase in pay.

I got a consultant gig from a company that I followed on Twitter. I sent a simple message that said, “I love your mission!”. A relationship formed and now we are great colleagues.

Instead of ignoring a press release, I responded and pitched an idea. It worked and now I have an exciting opportunity ahead.

Aside from these professional successes, I even found love the unconventional way when I was set up on a blind date by a friend. To be honest, I was not really into the idea. I could have said no, but I’m so glad I didn’t.

My whole point with this is that so often we think we are doing things the “right way” but they are clearly not working. Try to step outside of yourself and see what you could be doing differently.

Your approach is EVERYTHING. I cannot emphasize that enough. Your approach is everything. If your current approach is not working, stop beating a dead horse. Try something new.

Be bold, ask for what you want, and be confident in what you can deliver. We all have to deal with the perils of Impostor Syndrome coming to rain down on our parade, but get an umbrella and keep going.

You never know where a connection will lead. You never know where your next gig is coming from. Opportunities are right around the corner.

The key is to keep at it and put yourself out there, everywhere. Be unabashedly yourself. I know for a fact that my freelance business took off once people could “see” me — both literally and figuratively. I stopped hiding behind the mask of anonymity, put a picture up and started writing about things in my own voice that felt authentic to me and not veiled under fear.

If you’re looking to start a business, get a new job, fall in love, etc. and what you are doing isn’t working, try something new. Keep putting yourself out there on social media and follow-up with everyone you meet. Everyone.

Your network is your net worth, so foster your connections. Be yourself and believe there is something out there for you greater than yourself.

This post is in: Entrepreneurship, freelance, goals

November 12, 2014

As Thanksgiving approaches, I know many people will be leaving town, unplugging, and spending quality time with their families. I’ve never been much of a holiday person, which is why for the past eight years, I have always traveled on Thanksgiving.

For a long while there, I would head to San Francisco and eat at Silver Clouds, a diner karaoke dive, turned wannabe chic dinner joint on the holiday. Aside from SF, I’ve also visited Buenos Aires and Vancouver, B.C. during this time.

This year, I’m not going anywhere and I’m totally okay with that.

But here is what I want to do:  I want to work.

Yep, you heard me right. I want to work and maybe help you out. If you are a blogger that will be taking some time off during the holidays and need some help, let me know!

Do you want to keep a consistent publishing schedule? I got you covered.

Do you want to maintain your socially active presence? I can do that, too.

Or how about edit that e-book that has been sitting on your desktop for 4 months? I love editing other people’s work, so let’s get started!

Maybe you need some help with your resume, cover letter or dating profile?

Or perhaps you’re finally ready to get serious about side hustling. As a side hustle maven, I offer affordable side hustle coaching services to help turn your question mark into action and extra money.

Really, there is no task too small. If you need a writer, editor, social media scheduler, copywriter or virtual assistant, then let’s collaborate.

Here is what I can tell you about me and my services:

If I sound like the gal you need to help your blog and business survive the holidays, then get in touch with me at deardebt at gmail dot com with the following:




This post is in: freelance

As a new freelancer, I’ve learned a ton about staying on task and getting organized. I thought I was pretty organized before, but I realized that as a freelancer you need to be on top of your game or else you will suffer the consequences. When you have to follow-up about payments, stay on top of taxes, and emails are coming through at all hours, organization is key. Here are my favorite tools to stay organized and on task.

Google Tools

My second home is my email. I schedule everything in my calendar. If it’s not there, it doesn’t exist. In addition, I’ve made folders for all my clients and important projects. When I see people like my boyfriend who have thousands of emails in their inbox, I shudder. I’m not obsessed with inbox zero like some people, but I’m about inbox organized, so I rely on folders for that. I leave pertinent things that need catching up on in my inbox. I also do all my writing in Google Drive, which helps me save my work automatically and have it organized by client folder so it’s easy to access later.


Sidekick has been a total game-changer for me. I send out a lot of important emails and things that are time-sensitive. Because of this, when someone doesn’t respond, I often wonder, did they get my email? Well, Sidekick notifies you if people open your email! This has completely changed the way I run my business and how I follow-up with people. Enjoy a free month on me (no payment required upfront).


I use Asana to track all my deadlines and tasks. You can enter tasks, set deadlines, and add followers which is helpful if you are working with a group. I love the email reminders, as well as the organized workspace. The phone app leaves little to be desired, but I’m on my laptop most of the time.


Even though I loathe PayPal fees, it is easy to get paid and send invoices using PayPal when you are working as a freelancer. It’s great to see invoices in one place, keep track of payments, and manage clients. For others that don’t have an online business, but have a retail business, you can track your data, sales, payments, and growth.

Focus Booster

This is a useful timer that is based on the pomodoro technique, which states we work better with frequent breaks. The timer is set to 25-minutes, and then is set for a 5-minute break. I find this great for timing my freelance work and also reminding myself to take breaks!

Songza or Focus at Will

I love music and I just work better with it. I love listening to Songza which offers curated stations based on your emotions, preferences, interests, and more. I think it is 100x better than Pandora. I love listening to Blank Page, Melancholy Morning, Girls Night Pregame Jams (ha!), and much more. Also, Focus at Will is another great music option when I’m looking to really get in the zone. Focus at Will uses neuroscience to help you stay focused. I have no idea how it works, but I dig it. It’s free for thirty days, then a nominal fee. Haven’t forked over any money yet, but I like it.

What other tools do you use to stay organized?

This post is in: freelance

August was my first full month of being full-time freelance. It has been a wild month full of highs, lows, and uncertainty.

But this is what I signed up for, right?

And I love it! I didn’t realize how utterly exhausted I was until the transition. For the first two weeks, I took a nap. Every. Day. After working more than 80 hours a week for the past six months (and really I’ve been pushing myself for years, since graduate school), I was just simply exhausted.

It felt both oddly exhilarating and worrisome to freely take a nap in the middle of the day. I’ve now recovered and no longer take naps. I feel rested and happier than I’ve been in a very long time. I am now getting around 7-8 hours of sleep every night, compared to 4-6 hours before.

I have had some challenges, though.

Being a Night Owl

I have always known I am a night owl. It’s like as soon as 10pm hits, I’m ready to work! When I was juggling my full-time job and freelance work, being a night owl was helpful…until I still couldn’t get all the work done and was routinely waking up at 5 or 6am to get stuff done before work too. Now that I’m on my own, my inner night owl has taken over. I’m often working until midnight or even 3am. Then I sleep until 8-10am. Somehow it really works. So while I do my best work at night, during the day I’m often doing easier stuff like answering emails, responding to comments, etc. Easy stuff that doesn’t require much of my brain. I’m feeling really guilty not doing “important” work (although I’d still regard that as important – but it’s unpaid, nonetheless) during the day. But I still meet my deadlines. I get things done. It’s just at night, most of the time. Somehow I really enjoy working when I know most people aren’t, but I need to let go of the guilt of not being productive every waking hour.

Payment Schedule

Most of my freelance work pays me once a month. That’s a stark difference from twice a month. Luckily, I do have some event work and other gigs that pay me sporadically, but I swear I felt like I waited 3 weeks to get paid for anything. I was stalking the mailman, hungry for my check. I’ve come to realize I need to get used to this, which is why I’m going to continue to prioritize my emergency fund, to get me through those moments of paranoia. I know the money is coming, but I just have to wait.

Divorcing Myself from the Employee Mentality

For so long I’ve been in the employee mentality; I’m good at being told what to do; I behave; I collaborate; I play nice, sometimes too nice. But I’m the boss now. And that’s still hard for me to accept sometimes. I’ve been slowly pushing my boundaries and asking for what I want and need in several low-risk situations…and it’s worked out well. I realize I need to be more assertive and ask for what I want. No one is going to just give it to me. Action always beats inaction. I’m also realizing that what I think is a big deal in my head, really is nothing to other people. In short, these are my issues, not other people’s – to get what I want I need to get out of my own way and ask for what I want and need. No one is a mind reader, so be upfront.

So how did I do financially?

On one hand, I made more than I did at my old job…

But it was actually less, after you consider taxes…

And it’s definitely less than what I was making with my full-time job and side hustles combined.

But I’m happier than ever, rested, and I’m hustling. I have faith I will continue to grow and make more money.

For my first month out, I’m pretty happy with the outcome. But I have room to grow, too, so if you need a writer, editor, virtual assistant, social media manager or side hustle coach, get in touch!

While I won’t be sharing totals, you can see percentages of my income and where it came from:

63% of my income came from writing, editing, and virtual assisting.

35% of my income came from brand ambassador and event work. I work as a brand ambassador a lot and also have a very part-time job working for a local congregation in town as an event assistant. I always get free food and wine, too.

2% sales. I was able to sell some old stuff I didn’t need.

So as you can see, while I am making the majority of money online, it isn’t all of it. I like it that way too because I believe wholeheartedly in diversifying your income. The event work also helps me get away from the computer and gets me interacting with people face-to-face.

Some days I don’t leave the house, or I don’t leave until much later, and I’m so surprised by the sun and all the sensory experiences of being outdoors. Such a difference from the near fluorescent luminance of my laptop and the dark aura of my closet-turned-office.

So there you have it folks. My first full month in review. I can still hardly believe I quit, but I feel in my heart it was the right decision. And I’m excited for the continued adventure (especially at FinCon in 2 weeks! I’m going to FinCon camp, baby! Come see me at karaoke?).

p.s. If you haven’t filled out my survey, I’d greatly appreciate if you could spare 3 minutes for 3 questions. I genuinely want to make a better experience for you.

This post is in: freelance, goals

August 19, 2014

As a freelancer, it’s more important than ever to streamline your workflow and make your time count, especially when you are just getting started. Time is money after all.

In the beginning, I was so slow and everything seemed to take forever. As I got more clients, I started to feel so disorganized at keeping everything in order. There were so many little details I needed to remember.

I’ve (luckily) become more organized and smarter about the way I do business, so that I can spend time creating and not on the ever-pervasive follow-up (which is still necessary as a freelancer). Here are 4 tips for new freelancers to help streamline your work, stay organized, and work efficiently.

1. Set up a Google Alert for your name and your blog

Although I check my Google Analytics as well as my referrers in WordPress, I can’t keep track of everything. In order to stay on top of what is being posted about me or my blog, I created a Google Alert for my full name and my blog name. This is helpful, so you can keep track of what is being posted. Even if you don’t have a blog, this is useful for anyone to monitor their identity on the internet.

To get started, go to the Google Alerts page. Then enter the terms you want to be notified about. Then enter your email address and start getting alerts when those terms show up on a page.

2. Use a spreadsheet to keep track of clients, forms of payment, due dates, etc.

All clients are different and expect something different from you. To stay organized, I created a spreadsheet to keep track of my clients, how much they paid, due dates, how they prefer to pay, how they would like me to send an invoice, etc.

Instead of trying to remember how each client prefers something, I’ve just kept track of it in my spreadsheet. Some people are flexible with deadlines, while others have firm dates. Some people prefer to use PayPal, while others write checks. I need to keep track of these details, so I can follow-up and get paid and so that I have all the important details in front of me when I need them.

Click here to download your own client spreadsheet

3. Ask important questions upfront

Goodness, how many emails went back and forth when I just started freelancing? I’d have a million questions and think of them at different times, resulting in a million different emails.

That’s annoying. Your clients are busy and so are you, so don’t waste anyone’s time. Ask important questions upfront. Here are questions I ask when taking on a new writing gig.

– How many articles are you looking for per month? What are the deadlines?

– Do you prefer to receive articles in a Word doc, Google Doc, or via WordPress?

– How many words are you looking for?

– Do you want me to pitch topics to you or just write what I want? Or do you have ideas in mind?

– What is your budget and how do you pay? PayPal or Check?

– How and when would you like me to send an invoice?

These are my standard questions, but there are other questions you should consider as well. Where will your writing end up? Who are you writing to — i.e. who is the audience? Do you need to source an image? Will you get a link to your site or just credit? These are also important things to consider when starting out.

4. Create a separate tax savings account & save 30%

This year was the first time in my life I owed money to Uncle Sam. Fun times. Right after that, I vowed to save 10% of my freelance income. Well, I hate to say it, but I was naive. I need to be saving about 30% to cover my butt from any crazy tax bills. I also need to start looking into paying taxes quarterly. Save yourself the trouble and just save more for taxes. If you don’t need it all, you can use it elsewhere later. It’s a good practice to get into.

These four tips have helped me streamline my work as a freelancer and get to the point when taking on a new client. It also puts my mind at ease, because I am empowered with information so I can do my job well.

I hope some of these tips are helpful for you, too! Feel free to use or modify as you see fit!

This post is in: blog, career, freelance

These days I’m feeling very behind on things. I am absolutely thrilled that my dreams are coming true. I am working more as a freelance writer, and more opportunities are coming. In the attempt to manage my full-time work, and freelance work, every hour is seemingly booked and I feel so behind.

I think to myself, If I could only comment a little more! If I could only write 2 more posts a week for my own blog!

I think these things as if I were to do them, all other things would cease and I’d be “caught up.” The thing is, as I’m realizing, as an entrepreneur you are never caught up. Maybe you have met your deadlines, but there is another one looming right around the corner. Maybe you are done with one client, but you need to find another one.

The work is never over. Being caught up is merely a momentary sensation — more of something we tell ourselves so we can allow ourselves to relax.

I’m trying to be less hard on myself and be happy to focus on paid work. And even though I vowed to not apologize, I want to give a half-hearted lament that I’m not around as much as I’d like. I am reading, but cannot comment and share as much as I’d like. The less time I have, the more desire I have to be a part of the community.

Because I am just barely “catching up” with everything, I might be a little more absent. It might take me longer to do things. But I’m still around.

Check out where I’m on the web this week:

My First Job — life and money lessons I learned from my first job.

Is Working for a Nonprofit Right for You? — working in the nonprofit sector has its own set of challenges and rewards.

What’s the One Thing Holding You Back? — find out how my fear of failure has cost me money.

Some other posts I loved in the blogosphere:

Why Income Matters over at Well Kept Wallet, by the awesome Stefanie — I am making less in my day job than I did at 23. Granted, I have a much lower cost of living, but it still sucks. My hustling is slowly changing that, and I want to increase my income potential.

Weekly Roundup by Michelle at Fit is the New Poor — She quit her job and is now freelance! Show some support.

How are things in your world? How do you deal with your never ending to-do list?

This post is in: blog, career, freelance

As many of you know, side hustling is a large part of my debt payoff journey. I make a fairly low amount of money in relation to my debt, so for me to reach my ambitious goals, I need to hustle.

Side hustles have included: cleaning houses, washing dishes, working events, being a babysitter, selling water at a rave, being a brand ambassador, and a freelance writer.

One thing I pride myself on is that I think work is work. As long as I am in debt, there is no job too small or too big for me, and certainly nothing that is “below” me. I may have thought otherwise a few years ago when I had a fancy job title and managed several employees.

However, the 2 years after graduate school that I searched for a full-time job was a humbling experience. It was an emotional roller coaster for me and I felt like I took a dive in status.  I went from being a director of a program to cleaning houses.

I realized that perhaps I was wrong before. That I did think I was “too good” to do certain things, and now being forced to do whatever was available humbled me and deepened my understanding of the human experience, and this bizarre class structure we’ve created.

Now I have a full-time job that’s pretty rad. I’ve learned a ton of new skills that are highly marketable, and I’m having fun. I’ve also started this blog, and I’m seeing it as an opportunity for other doors to open. At least I hope a few will.

My current long-term side hustle that I’ve been doing every weekend for the past three weeks, and will continue for another five, pays $10/hr.  It’s a pretty low amount, and of course I’d love to be paid more, but here is the scoop:

Part of me is really proud of myself. I do things that I know my friends won’t do; I meet crazy people who are like characters from the circus; I have odd, amazing experiences; I get out of my routine and my comfort zone.

Most of the time, I’m very happy about my hustling. Other times I start to think that I might be selling myself short.

I have a master’s degree in something fairly useless, but it’s given me the ability to write. I also have management experience, as well as outreach and communication experience. I also speak Spanish, which has helped me land almost every job I’ve ever gotten. Shouldn’t I get more than $10/hr?

Yes, of course, I should. But these jobs I do on the side don’t require any of those skills.

I also think if you have the time available, then making some money is better than none.

Right? Or is it holding me back from pursuing larger paying side jobs? I really want to focus 100% on my blog; I want to update it more frequently, write good content, get paid to write content, and continue down the many avenues of creative employment.

But I’m not there yet. I can’t in good conscience turn down legitimate, albeit low paying work with how much debt I have.  I stand by the fact that work is work. Sometimes I just wish I could throw myself into this head first and reach my full potential.

What do you think? Am I a #1 hustler or am I selling myself short?

This post is in: freelance, goals, side hustle

February 17, 2014

I finally got my taxes settled this weekend and for the first time in my life I owe the IRS money. After some back and forth, and crunching the numbers, I owe roughly $300. Earlier iterations proved to be much higher, but were due to human error (note: triple check your taxes!)

I’ve always been one to gloat over tax refunds. That has been extra money towards my student loans, partial vacation funds, and saving cushions.  I was making such a low income before I got my current job (16k/yr), but doubled that this year by finally getting a full-time job. I hustled all through out this year and made close to $5k in side hustle income.

In the past 2 years I’ve been hustling, I guess the low-income and the untaxed income just evened out. This year I continued and didn’t give a thought to paying taxes on my independent contractor income.

I know, I know. Total PF fail.

I’ve really learned a lesson here. Although $300 doesn’t seem like a lot of money, it felt like a huge burden to me. It’s almost my half of the rent. It’s practically what I pay in interest per month on my graduate loan. This $300 sparked so many conversations this weekend. Because I have depleted my savings and choose to throw almost all extra income toward debt, I have very little fluid cash to work with. This means I will inevitably have to lower my student loan payments a bit, which really sucks. But here are the steps I’m taking to get through it.

#1: Start a Tax Savings Account

After I realized I was going to owe, I immediately started a tax savings account. The great thing about Capital One 360 (affiliate link) is that you can have sub-savings account. When I got paid on Friday, I transferred over several hundred dollars to my new account to ensure that I had funds available to pay my taxes. Going forward, I will put 10% of all my 1099 income in my new tax savings account, to prevent this from happening again!

#2: Don’t Panic

I’m not going to lie, I panicked a bit when I found out I was going to owe. Sadly, I didn’t even think that it was a possibility. I have been so focused on paying off debt, I hardly thought about my taxes. My empirical evidence gave me no reason to think I would owe. But the good news is I made more side hustle income this year! The bad news is I need to pay taxes on that biz! All this to say, panicking doesn’t help or change the situation.

#3 Don’t Get Discouraged

The only certainties in life are death and taxes right? Don’t get discouraged. Unfortunately taxes are a part of life.  You are a not alone. You are not a loan. This will be just one more thing to get over.

I will be paying my dutiful part to the IRS in the next few weeks. I will look forward to the side hustle income actually hitting my accounts in late February, early March. Although I’ve felt a bit down about this unexpected money, it just reminds me that the debt repayment journey is a process. It’s ups and downs, plateaus and setbacks; the main thing is that you got to keep going!

Have you done your taxes this year? Are you expecting a refund or do you owe?


This post is in: debt, freelance, life, pf-fail, taxes