3 Pricing Strategies to Make Money (and What to Consider to Make the Best Decision)

As business owners you want to make money and get paid (right?)...but most solopreneurs don’t take the time to back up to confirm that their pricing strategy has them set up to make money.

Which means oftentimes, there’s a better option.

And it’s worth looking into, when a better pricing strategy means you get paid more or more consistently so you can make those adventure plans happen, enjoy friend dates to the movies, go camping with the family and/or buy that new ‘thing’ you’ve been lusting after.

In this post, I’m digging into the most common pricing strategies: retainer, project, and hourly pricing; peeling back the layers of each one to understand the pros and cons, keys to success and views from the client side.

Let’s get started.

Pricing strategy #1: Retainer-based pricing

A retainer is a pre-set fee for a set period of time. The fee holds a set number of hours to do work during a specific period. Retainers generally don’t specify the type of work to be done. Virtual assistants, graphic designers, and website maintenance professionals frequently use a monthly retainer for a set number of hours.


  • Virtual Assistant: 10 hours a month, $200
  • Graphic Designer: 5 hours a month, $300

Pros, as a biz owner:

  • You can predict your hours
  • You can rely on steady income
  • You can work with clients consistently and build longer term relationships

Cons, as a biz owner:

  • Multiple clients may all request use of their hours at the same time
  • Vacation, illness and time away coverage is essential since your time has been committed and paid in advance
  • Projects may require more hours than the retainer covers since clients may be uncertain what projects would be needed or how long it takes
  • Without proper planning, you may not know what type of projects you’ll be asked to do can lead to projects outside your expertise

View from the client side:

  • Great for routine activities
  • Predictable monthly expenses
  • Use or lose: may not use all the hours purchased

Key to success with retainer-based pricing:

  • Set clear guidelines on how you’ll work together and your work hours (which may not include email requests at midnight or phone calls at 7am). This avoids clients who expect you to be ‘on call’ for those hours they’ve purchased.

Pricing Strategy #2: Project-based pricing

Project-based pricing: a pre-set fee for a specific product or package with a defined set of components. This pricing strategy is based on delivering an agreed-upon result regardless of hours or costs it takes to do the work.


  • Squarespace website set up with four page layouts, $1,500
  • E-course content development with 10 lessons, 5 worksheets and 3 videos, $997

Pros, as a biz owner:

  • Ideal for routine types of projects when you can easily calculate the time required
  • Increases ability to predict income
  • Incentive to minimize your time, be efficient and still deliver a quality result

Cons, as a biz owner:

  • Difficult to estimate pricing if you haven’t completed enough similar projects
  • Have to manage client expectations for elements not included in the defined project (scope creep)
  • Projects may take longer than you estimated, which means less profit for you

View from the client side:

  • Easy to know and plan for the project cost
  • Lack of transparency to the level of effort required for the project
  • Project definition may not exactly align with what they need

Keys to success with project-based pricing:

  • Be diligent in defining what’s including and not included in the project and how requests outside the definition will be handled
  • Don’t be afraid to iterate your packages with what you learn each time you do the project

Pricing strategy #3: Hourly pricing

While perhaps not the most advantageous, hourly pricing is by far the easiest to implement and is, from my experience, the most commonly used pricing strategy. Hourly pricing is simply the price charged for each hour of work.

Pros, as a biz owner:

  • Easiest to use
  • Increases likelihood of being paid for all the hours you work (if you estimate well in your proposal)
  • Great approach if you haven’t done many projects
  • Easiest for managing time off

Cons, as a biz owner:

  • No incentive to be efficient with your time
  • Requires you to work a set amount of hours to reach your revenue goal
  • Difficult to incorporate value as part of price

View from the client side:

  • Most transparent pricing
  • Easiest to compare between competitors
  • May not get most efficient work from you

Keys to success with hourly pricing:

  • Ability to provide a solid estimate of the time required for a project
  • Clarity on what’s included in the scope of work for the time and price and how requests beyond the scope will be managed

Choosing your pricing strategy

What makes the most sense for your business where you’re at today? Consider your ideal clients, your specialty, and the results you can deliver. Know yourself and your ability to estimate time. Give your ideal clients the best opportunity to say yes(!) to working with you.

But perhaps most important to know is this: You don’t have to pick only one pricing strategy. Offering a combination approach may make the most sense for you and your client. Have a routine set of activities you offer? Consider project-based pricing, with hourly pricing for additional, ad-hoc requests. For highly customized and tailored services, retainer and hourly rates may be ideal. Offer a retainer package of hours then add in hourly rates for unexpected needs.

(What you should charge for your services is a separate and super important topic, too. Be sure you understand both your pricing strategy and what you should charge, because they go together like wine and chocolate or peanut butter and jelly. Yum.)

The easier you can make pricing for your clients, the easier it will be for them to say yes. It makes it easier for you too, so you can spend less time on preparing proposals and talking about pricing, and more time doing the work and growing your business.

PS: Want even more on pricing? Rebecca Tracey’s Get Paid (How to Price Your Services + Programs) e-course will be in this year’s Solopreneur Success Bundle! Head over to the Bundle page + sign up to get notified when it launches in September.

Tools We Love: Gmail’s Canned Responses

Tools We Love: Gmail's Canned Responses

Tools We Love: Gmail's Canned Responses

Welcome to Tools We Love, where we highlight some of the tools that make us more efficient, productive, and effective in our businesses. Have a tool that you want to share with the community? Email us! Today’s tool we love: Gmail's Canned Responses!

We did a quick search on One Woman Shop and were shocked to find out that we’ve only mentioned one of our favorite tools -- Gmail's Canned Responses -- exactly once in the past several years. (Hey, with 46 pages of blog content, we can’t remember every single thing we write.)

So, this post is a long time coming, though we do talk about Canned Responses in The Solopreneur Sanity Handbook. File this topic under “things that are second nature to us but new to many other people.” (We bet you have plenty of those things too, even if you’re not aware of them.)

A quick overview: Canned Responses are a Gmail Labs feature (Labs = “a testing ground for experimental features that aren't quite ready for primetime”) that allow you to save templates for the emails that you send often. Think: answers to FAQs, your client onboarding process, or step-by-step instructions.

Hands-down, the biggest benefit of enabling Canned Responses is saving yourself time. But we’ve recently uncovered another big benefit: Using Canned Responses can help you remove some of the emotion when you need to deliver negative news, like an application rejection or sponsorship request.

Here’s how to get started:

  1. Go to the Settings wheel on the top right of your Gmail account
  2. Select Settings
  3. Go to Labs
  4. Enable Canned Responses
  5. Hit Save and your inbox will refresh
  6. Next time you compose an email, hit the bottom right-hand arrow in the new message to see (or save) a Canned Response

Here's what it looks like:

Tools We Love: Gmail's Canned Responses

Voila -- the next time someone asks about your contributor guidelines or how your pricing works, you can reply with just a few clicks! Of course, we highly recommend adding a personal touch to every email -- but this gives you a solid base from which to work.

Here’s your challenge from One Woman Shop: Every time you send an email over the course of the next week, ask yourself “Will I likely send this same email again?” If so, save that shit as a Canned Response right away. (Pardon our French -- we get amped up when it comes to saving time.)

Questions For An… Accountant

Questions For An Accountant

Questions For An... Accountant

One Woman Shops can’t always do it all. But when it’s time to turn to an outside pro -- and be certain we’re choosing the right one -- we’re often at a loss as to what to ask to get the info we need. Welcome to Questions For A… a series where we interview the pros themselves on the questions you need to ask before hiring them.

In this month’s edition, we bring you Questions for an....Accountant with contributions from accountants Amy Northard, Taisha Stewart of Saidia Financial, Catherine Derus of Brightwater Financial, and Erin Johnstone of Vivid Numbers. Here’s what they suggest you ask, and why:

Q: What services do you offer? What services are included in my package?

Amy’s why: Just like specializing in different industries, accountants can specialize in different financial services. Make sure your needs (tax planning, budgeting, etc.) align with what they can offer.

Tai’s why: Clearly define the scope of services you need or won’t need because you don’t want to be charged for a service you don’t need, nor do you want to be unaware of what’s included in your accountant’s quote. Some accountants provide tax preparation as well as monthly bookkeeping services. Some process payroll (which can include 1099s). Some accountants provide quarterly review meetings with the client, while others only talk to their clients once or twice a year. You want to make sure that there are no surprise charges down the road. Know what to expect from your accountant and when to expect it.

Catherine’s why: An accountant may provide any combination of the following services: tax preparation and planning, business formation, bookkeeping, payroll processing, financial and retirement planning, cash flow and budgeting analysis, and more. If the accountant you plan on hiring doesn't provide a service you need, ask if they have recommendations.

Q: Do you have experience in my industry?

Catherine’s why: Different industries come with their own unique accounting and tax issues. Accounting for a food blogger (are you tracking food purchases for recipe development?) is different than accounting for a retail store (hello, inventory!), which is also different than accounting for a freelance writer (do you have all of your 1099's?). Your accountant should be aware of tax opportunities that relate to your industry.

Erin’s why: There are standard tasks in accounting and bookkeeping regardless of industry that any good accountant will understand. However, you'll get more value from someone not only familiar with your industry but who has experience in it as well. You are essentially paying for the knowledge the accountant can bring to the table so the more they already know, the better!

Q: How can you help me grow my business?

Catherine’s why: Businesses have several moving pieces and an accountant can help you see the big picture by assisting with a business plan. At the same time, they can provide suggestions on your pricing, improving cash flow, assessing whether to hire an employee or contractor, and other ways to improve your bottom line.

Q: What bookkeeping software do you primarily work with, and what is your preferred method of communication?

Catherine’s why: Gone are the days of schlepping a shoebox full of receipts and a folder full of statements to your accountant's office. Unless, of course, your accountant really wants you to! These days, accountants are using cloud-based accounting programs and file-sharing sites, emailing contracts and invoices, helping you track expenses with online receipt scanning, and communicating via Google Hangouts or Skype. When you have questions, figure out if your accountant prefers a phone call, email, or something else. When I work with financial planning clients, we have a set number of in-person or virtual meetings throughout the year, but I offer unlimited email support in implementing planning recommendations.

Amy’s why: Many accountants have a preference as to which bookkeeping software they use because they're most familiar with it. Familiarity means they can work more efficiently and offer advice if you have any problems with the software.

Erin’s why: We all know that communication is critical in business relationships, and it's no exception here. Look for someone who has the same preferred method of communication so it flows more freely and frequently. You can quickly become frustrated (and vice versa) if you always want to hop on Skype for a video chat but your accountant wants to respond with an email.

Q: Are you available during tax season?

Erin’s why: "Busy" season is a very real thing for accountants who also prepare taxes. You want to make sure your accountant will still have the capacity to assist you the first three and a half months of the year and not just go dark!

Q: What will your help cost me + how do you bill?

Amy’s why: Most accountants don't have detailed costs for their services listed on their website because client needs can vary so much. Ask about this up front so you aren't surprised with a big bill.

Erin’s why: Find out if you will be billed by the hour or if there will be a fixed fee. If by the hour, you will also want an estimate on what the fee will be. Along the same line of thought, you'll want to know exactly what you are getting for your money.

Q: What systems and processes do you have in place to protect my financial data?

Tai’s why: Your accountant will have access to the most private information you possess. You want to make sure that your financial statements aren’t just lying around for anyone’s eyes to see. Also, social security numbers, addresses, and other private details should be under lock and key or encrypted digital storage.

Q: How quickly should I expect deliverables to be available every month?

Tai’s why: Clear communication prevents misunderstandings. I was recently interviewing a new client whose main problem with his previous accountant was that he didn’t get information to him in a timely manner. Expectations should be outlined upfront to keep you happy and to also give the accountant the time necessary to make information available to you. For example: Will I be receiving my monthly profit-and-loss report by the 10th of the following month? Should I start to worry if I don’t receive it by the 5th? What deadlines can I expect you, the accountant, to adhere to?

Q: If I incur federal or state penalties for filing errors proven to be the fault of you, the accountant, will you reimburse me? And if so, how much?

Tai’s why: Again drawing from client narratives of past accountant relationships, an accountant is human and sometimes mistakes are made. If that accountant is filing tax returns (business or personal) or making estimated tax payments on your behalf and causes you to incur penalties or interest with the IRS because of neglect or oversight, what is their policy on resolving the situation? Perhaps they will reduce what they bill you. Perhaps they will pay part of the penalties.

Ready to grill (in the best way possible) your potential accountant? Print these questions out + have them at the ready when you’re looking to hire! And if you want pros we stand by, check out the One Woman Shop directory.

PS: Want more information from accountants on what to know before you hire them? Get the (free) Prior to the Hire ebook now!

Think It’s Not a Big Deal? Why Even the Simplest Partnerships Need a Contract

Why Even the Simplest Partnerships Need a Contract

What I've Learned from Our One Woman Shop Partnership

We’re writers and consultants, designers and photographers, front-end developers and store owners. And despite our differences, if you’re anything like me, emails with some variation of “Hey! I have an idea we could tag-team” pop up in your inbox frequently.

Entering into even the most casual of partnerships begs us to pause and protect the business we’ve worked so hard to create. Sure, “partnership” conjures official, legal agreements, but in actuality, a partnership can be anything from an Instagram loop giveaway, styled shoot, affiliate link, co-hosted webinar or e-course, conference, breakfast panel, or even a guest blog.

But for something as small as these examples, do you need a contract? After all, you’ve got a budget to balance, receipts to file, proposals to draft, and deadlines to meet. Who has the time to comb through an email thread and delineate terms and conditions?

No contract? Here’s what could happen

Time and again as I wade the freelance waters, I turn to Christina Scalera, a lawyer for creatives. According to Christina, yes, you need a contract even for small partnerships: “Ninety percent of [creatives] can avoid lawyers -- the expense, heartache, and more -- by communicating upfront and honestly in a contract,” she says. “Lack of a contract can lead to problems down the road if you’re not careful.”

Without a contract in place, we could:

  • Finish up a styled shoot to find no photos of our 12 hours of calligraphy work were even submitted to the publication
  • Partner to form an Instagram community, only to find a sneaky cohort is slow to hand over the login
  • Trade headshot photos for copywriting with a writer who just can’t seem to ever get to your bio

But first: Is the collaboration worth your time?

Before I send you into a downward spiral of researching what goes into contracts (editor’s note: start here!), pull out a pen and paper to figure out whether this collaboration is truly worth your precious time. If your hourly rate isn’t already on a sticky-note on your screen, follow these steps to find a rough calculation:

  1. Take what you need your salary to be (after taxes), and divide it by 0.7. That dumps back in an estimated 30% in taxes.
  2. Add your monthly business expenses, times 12.
  3. Divide that number 52.
  4. Finally, divide that by the number of hours you’re willing to work each week.

Back to the sticky-note: It helps me so much to think back to my PR agency billable days every time a joint venture, guest blog, affiliate, or partnership opportunity flurries across my inbox. Picture yourself on the project -- for me, that means seeing the project fit into my ink-splattered world of calligraphy and copywriting projects. For you, that may mean thinking through the creative brief, wondering how many hours you’ll log in Photoshop and Illustrator, and how many rounds of edits might be needed. Consider exactly what this partnership project require from you, then ask yourself this:

Are both the partnership ROI and the time I’ll invest in the partnership worth my hourly rate?

In many times, yes! As Christina mentions, guest posting is a great example: Essentially you’re doubling your reach. Market research tells us that it takes anywhere from 3 to 12 touches to nab that customer, meaning leveraging your voice by getting in front of others’ communities can be a rock-solid business investment.

Reassuring you a bit more, don’t fret over “legal-ese” verbiage: Technically, if both parties understand the language, it can go in the contract. It’s your catch-all. At the end of the day, much like my desk holds my calligraphy pen, nib, inkwell, gouache tube, and sketchpad, a contract holds together all the little fragments of email threads and promises between collaborators, tying them neatly together.

Truly, while you could manage promises de facto through your email thread, I’m a fan of a drawing up a quick proposal within my Honeybook account and emailing it over. It takes under an hour -- totally within my budget considering my hourly rate and what lack of a contract could cost me.

What to include in your contract

Like any good millennial, I’m in a constant state of information overload, and need an actionable takeaway for an article to stick. So, here’s your simplified partnership checklist! As you send over that proposal partnership template, review these questions:

  • Am I clear on the profit split, if any?
  • Did I write out dates of deliverable deadlines -- and project termination? (And reminder, this doesn’t mean relationship termination!)
  • Have I addressed the exit strategy, and listed the means that could allow the contract to be terminated and how the assets would be divvied up if so?
  • Who will own assets -- both during the project and moving into the future post-partnership -- from email lists and social media accounts, to final copy and leftover swag bags?
  • Did we jot out a list of tasks, and who will be responsible for what?

There you have it! Simpler than it sounds, right? Let’s save the freelance world of lady boss friendships-gone-angsty, one kindly worded contract at a time.

Need inspiration?

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Compatible Collaboration: How to Pick Your Perfect Partner

How to Pick the Perfect Business Partner

Compatible Collaboration: How to Pick Your Perfect Partner

Collaborating with a fellow solopreneur is a great way to expand your business and explore new platforms or markets -- without all of the pressure of trying to figure it out on your own. But partnering up with just anyone can make for a collaboration that brings more stress than success.

When you’re on the hunt for the perfect partnership, keep these essentials in mind.

Where to find a collaborator

While you could bump into your collaboration soulmate while walking down the street, there are two places in particular I recommend looking for potential partnerships.

1. Online communities: Membership communities like One Woman Shop are a great place to connect with like-minded business owners who are open to collaborating on a business or marketing idea. This is especially powerful when the group brings together solopreneurs from various fields and areas of passion or expertise. (Editor’s note: Just look at what OWS members Jill and Julienne recently brought to life!)

If you’re not yet a member of a community like OWS, free Facebook Groups are another great place to connect with potential partners. Chances are there’s someone whose posts have caught your eye, and if you’ve felt the spark, they may be the person to ask.

2. Group courses or programs: When you’re in a group course and interacting with the rest of the students either in a private community or on group coaching calls, keep your eyes open for potential collaborators. While you and your cohorts are developing a specific skillset alongside one another in the program, you’re also sharing your individual strengths and passions, and there could be a perfect match in there for an idea you’ve had brewing.

Of course, those aren’t the only places; they just happen to be my top recommendations. Here are a few other places to meet business partners:

  • Social media: Stellar Instagram shots or witty Twitter banter could lead you to a good match
  • Real-life networking: Making small talk and exchanging business cards at a conference or event can lead to partnerships
  • Your business community: A subscriber to your email list may impress you with their responses and engagement
  • Your social circle: Friends or family could be a great fit -- just be aware that mixing business and friendship can create high stress situations

Collaboration compatibility

Once you’ve set your sights on a potential partner, it’s time to do a bit of research and reflection to determine if you’ll be a good fit, and if the signs are pointing to a profitable collaboration. Here are the three must-haves for a strong match:

1. Balanced skill sets: If you and your potential partner are both bringing the same skill sets to the table, your partnership is going to be rocky. While your combined expertise may trump any and all competitors, you’re going to be left with some serious skill gaps that will create extra work and stress for both of you. Your best bet is a partnership where your skills will complement one another’s. Even then, you’ll inevitably have gaps, in which case outsourcing will be key.

2. Similar styles: Branding is important, and goes beyond the color palette you use and the funky fonts on your site. It extends into your language, communication and tone -- and is designed to attract more of the clients you love working with. A collaboration will struggle when there’s a big difference between the tone of your business and your partner’s. If your presenting style is upbeat and bubbly, and you partner with someone who communicates with a brash, in-your-face tone, your audience is going to be 1) confused and 2) turned off by one or the other of you. This leads to poor sales results and frustration for both of you.

3. Aligned expectations: There is a vast variety of projects that you can collaborate on. Blog post exchanges, webinars, courses, even full-on joint ventures or new companies. So being on the same page when it comes to what the vision is for the project (World domination? A fun side gig?) as well as how each of you will be investing when it comes to time, finances and energy is important. The saying is true: You can go farther when you go together...but with the caveat that you need to have agreed on the destination ahead of time.

Picking that perfect partner

In the rush of excitement of launching a new partnership or collaboration, it can be tempting to skim over the research and reflection on whether or not you’ll be compatible. True -- some of the must-haves can be managed or massaged with clever contracts and strong communication later on, but spending some time assessing the strengths and challenges your collaboration will face ahead of time can save a lot of heartache and frustration down the road.

Have other tips for finding the perfect partner? Share with us in the comments below.

When it Comes to Tax Time, Here’s How to Avoid the Panic Like a Boss

April 15th strikes fear into the hearts of many entrepreneurs, and for good reason -- once we’ve worked hard at becoming profitable, the last things we want to think about are tax payments, CPA prep fees or (gasp!) being audited.

I see that glazed-over look of “tax-time horror” on the faces of my coaching clients often. But based on my background as an accountant and auditor, I can attest that tax time is much less stressful if you’ve already conquered half the battle: having organized documentation. On April 14th, you don’t want to be scouring the depths of your purse for a receipt from that one expensive bill paid way back in January.

Now, tax time may have come and gone for this year (phew), but there’s no time like now to start making things easier for the next go-around -- especially because the panicked search detracts from your peace and can be circumvented easily.

Even better? Getting your documents organized can be fun, manageable and save money. So, if you’re cringing at the thought of calling an accountant, staring at piles of old receipts or just putting it all off until the last minute (again), I have a few simple, actionable tips to get your critical items in order so you can get on with the business of being a solopreneur #bosslady.

Ready? Let’s do this.

Make organizing fun and manageable

Some of us love to be organized, and some of us don’t. But here’s the key: The more organized you are during the year, the smoother your tax season can be. Whether you’re already behind, with your receipts piled up in a drawer for “later,” or you’re just getting started in biz, approach it the same:

  • Pick up colorful file folders and use your favorite Sharpies/pens to label them with descriptions of the file contents (cable bills, pay stubs, bank statements, etc.)
  • Grab a pile of receipts/invoices/forms and start organizing them into the appropriate folders

Are you all about digital file-keeping? Google Apps or Dropbox are great options to hold your documents. Both have free versions, offer file-sharing to others (like your accountant), can be used on your mobile device and can even be color-coded, just like those handy, physical file folders.

If you’re looking for a service that does more than simply house shareable documents, Shoeboxed offers IRS-accepted receipt organization, automatic archiving of invoices from Gmail and even a GPS-enabled app to track your vehicle mileage. This option has a free 30-day trial with subsequent payment plans currently starting at $9.95 per month.

Organizing your receipts and files can be accomplished while watching TV or listening to a podcast if you have a larger chunk of time, or gradually over the course of a week if you only have a few minutes each day. Breaking it down into a few minutes each day or combining it into another activity (hello, Netflix!) helps it feel more manageable.

Bonus points: Keep both a hard copy of all documentation and an electronic copy in at least two places. Proving income and expenses to the IRS could be a mini-nightmare if you lose the only copy of your detailed receipts. (Editor’s note: Scan your receipts in with your phone using a handy app like CamScanner!)

How to organize receipts + files within your folders

For the most user-friendly filing system, group your files into categories that would mimic your financial statements (revenue and expenses). For example, a revenue folder might contain sub-folders containing documentation for:

  • Commissions Earned
  • Income from affiliate programs
  • Tips Earned
  • Advertising Income

Similarly, an operating expenses folder would contain sub-folders for:

  • Payroll and Related Fees
  • Vehicle Mileage and Maintenance
  • Meals & Entertainment
  • Advertising Expenses
  • Software and Technology Service Fees

Grouping files into categories allows an accountant to more easily and accurately find what they need to file your returns. And in the event of an IRS audit, it could save you many stressful hours of digging through a stack of uncategorized files.

Organizing saves money

Another reason to organize your records: It can save you money. Having a brief summary of the year’s transactions can work as an excellent bargaining tool for reduced tax prep fees because most CPAs prefer getting a neat, concise schedule instead of a shoebox full of coffee-stained receipts. (A quick reminder: An accountant compiles the information; the IRS audits it.)

I highly recommend my clients regularly export their online financial account activity and maintain an electronic copy. Then, when tax time rolls around, they can easily summarize the year’s financial data to hand off to their accountant.

To do this, you can use budgeting or banking apps, or if you want to get nerdy with it:

  • Export online checking/savings account activity to Excel
  • Add a pivot table to the data in Excel (learn how to do it here or here)
  • Set up the pivot table to summarize by type of transaction, vendor, etc.

I am in love with using pivot tables on my exported Excel-format banking info because it provides 1) a quick summary of income and expenses by type for your accountant to use in tax filings, and 2) the underlying detailed transactions you would need if audited by the IRS.

If you use Freshbooks, Wave, or other bookkeeping apps, you can export reports, as well.

Getting your records organized can not only work as leverage for a potentially reduced tax prep fee but also illuminate forgotten expenses that help offset some of the year’s income, effectively helping to reduce your tax liability.

You can do this (really!)

The simple take-away: Organizing your tax records is 100% manageable, can save you precious dollars to reinvest in your business and can even be enjoyable when approached creatively. Give it a try and see if it provides some ease to your process. Happy tax season!

What were your greatest tax season pains this year? Leave them in the comments!

PS -- Feel like it might be time to learn more about those solopreneur finances? Check out Solopreneur Finances, a course we co-created with Carrie Smith of Careful Cents -- that just happens to be included in the One Woman Shop Bundle!

We Need To Talk: How To Effectively Deliver Feedback

Outsourcing for your solo biz via @OneWomanShop

outsourcing for your solo business via @OneWomanShop

In a perfect world, you’re a solopreneur with a perfectly assembled team of specialists to outsource to, who you’ve onboarded with ease. Your business is running like a finely tuned machine. Work gets done on-time, with expert quality, and all the moving pieces gel sublimely.

Except that sort of situation is exceedingly rare. So at some point you’ll find yourself in the position of needing to sit down with a member of your team and have “a talk” about how they’ve missed the mark or delivered work that isn’t up to your standards.

This can be awkward, nerve-wracking, and frankly something you would just rather not do -- but it’s got to be done. Fear not, because today you’ll learn how to effectively deliver constructive criticism to your team, minus the panic.

Get clear on the issue

The foundation of a low-stress feedback session with a team member is being prepared. Getting crystal clear on the exact issue will help you stay focused during the conversation, and will also yield the best results. Is there an issue with timeliness or lateness of their work? Mistakes or errors slipping through the net and into your hands (or worse yet, the clients’)? Or perhaps what they’re delivering is technically correct...but is missing the mark in representing your style and brand in the best way possible.

Being able to summarize the issue you’re experiencing in a short sentence or two will help you avoid accidentally rambling or skirting the issue. For example: “We need to address that your last three articles have been late.”

A tip: One way to proactively avoid these issues in the first place is to have a stellar onboarding process. Process docs are critical in onboarding.

Schedule the feedback

Delivering constructive criticism to a contractor isn’t the sort of thing that goes over well as a surprise. No one likes to feel as though they’ve been put on the spot. Schedule a meeting at least a week in advance, preferably to take place on Skype or over the phone, if you’re working remotely. Email may seem like the quick and easy way to take care of delivering the feedback, but it lacks the two-way communication that’s essential in avoiding misunderstandings. The goal is that you’re both feeling prepared and comfortable when the time comes to share your thoughts on where improvement is possible.

A tip: A classic method of delivering feedback is the Sandwich Technique, where you deliver the criticism “sandwiched” between two pieces of positive feedback. On the surface this seems like a great idea because it lets you get the conversation going with a low-stress compliment, deliver the negative feedback, and then bring the tone of the conversation back to a positive place with some more sweet words. Everyone leaves feeling pretty great!

But delivering feedback is about creating change, not warm fuzzies, so I recommend avoiding this technique when you’re delivering feedback to your team. It dilutes the importance of the critique you’re giving. There are times for positive reinforcement, and times for criticism -- mixing the two can leave everyone unclear on where they stand.

Bring solutions to the table

Identifying the problem is only half the journey in improving your team’s performance. Think back to high school and what it was like to get a big red X on a math exam. Not much use to you in figuring out what to do differently the next time. But the teacher sitting down with you and walking you through the better/correct/more efficient way of solving the problem meant that you were building a skill set that’d help you ace it the next time around.

Same goes for our businesses. Provide the criticism, and the skills or tools they’ll need to get it right. Below are some you solutions you might propose.

If the issue is...

  • Timeliness: Ask what’s causing the delays, and explore how you can help them hit deadlines. Consider offering to reschedule deadlines to another day of the week to avoid overwhelm in their calendar, or commit to giving a minimum advance notice on work you need done.
  • Errors or omissions: Review onboarding materials and offer to provide additional training on the issue areas. Screen sharing, recorded guides and manuals can be great supplementary materials to guide the team in hitting your expectations.
  • Brand or tone: Provide examples of language or visuals that are on brand, or assemble a style guide to help with consistency. You could even book a follow-up call to workshop some of their lacking/off-mark deliverables and help them understand why and how to adjust going forward (just like our math teachers walked us through the tough questions).

Encourage communication

Feedback goes both ways, and establishing regular check-ins with your team members gives you an opportunity to exchange feedback. At first, team members may be hesitant to share their thoughts on how you could do better (or differently) to help them be successful at their work, but handling their feedback with grace -- and taking action to adjust course -- will go a long way in fostering that flow of communication.

Having the hard talks is part of being boss

Discussing opportunities for improvement with a team member is never pleasant -- but as a solopreneur, it’s an essential skill that will help you cultivate a strong network of contractors and specialists that can help you deliver your best work to customer and clients. Focusing on clarity, solutions, and being open to receiving suggestions will help you make the process as stress-free and productive as possible.

Your turn: What difficult conversations have you had to navigate as a solo biz boss?

What I’ve Learned from Our One Woman Shop Partnership

What I've Learned from Our One Woman Shop Partnership

What I've Learned from Our One Woman Shop Partnership

Lately, the topic of collaborations and partnerships has been hot on our minds here at OWS. It's been coming up on our coaching calls, in the members-only Facebook Group, and it's officially our topic of the month on the OWS blog. We thought it might be appropriate to kick it off by pulling back the curtain on OWS HQ to share our tips on being an awesome business partner or collaborator.

Fun fact: Though our name is One Woman Shop, we are technically a two-woman shop! (Want more about our background as a team? Hop over here for story time.) Even if you aren’t looking to establish a formal legal partnership, we bet you’ll want to collaborate on a project, e-course, ebook, or webinar during the course of your solo biz.

Our partnership isn’t perfect, but I (Cristina) know I speak for both of us when I say we’re pretty darn proud of the relationship we’ve built. (Especially since we’ve never met in person.) Together, our ideas are better, our execution is better, and our fun is more funner. Seriously, we laugh a lot on those video calls.

Here’s what I have learned from working closely with a business partner (that would be Sara) over the past few years -- lessons she would share when asked, as well. A giant caveat: Alas, I do not always act 100% in accordance with this advice, though maybe I will one day 😉

Work together but divide and conquer, too

There have been about 1,567 times when I couldn’t seem to break through a mental block without having a giant brain dump session with Sara. Sometimes all you need is to get on a call with someone to move forward. On the flip side, we have a tendency to over-rely on each other. What if the wording of that two-sentence email isn’t just so? Defining dominant areas of work for each person can be incredibly helpful. For example, Sara is the go-to for our editorial calendar and all guest posts. While she takes the lead on all related elements, she’ll sometimes loop me in for additional perspective or insight.

Learn when to take a stand -- and when not to

I have strong opinions. Working with a partner has taught me the importance of choosing when to take a stand and when to let things go. Let’s say hypothetically that you get a finite number of “trump cards” each day or week. I like to ask myself the following: “Is this thing right now the thing you want to take a stand on?” You might ask yourself “On a scale of 1-10, how important is this to me?” If it’s a 2 (you care a tiny bit), communicate that. If it’s a 10 (you wouldn’t feel comfortable or even ethical if you didn’t fight for this thing), communicate that. Spoiler alert: You can’t always be a 10. Another spoiler alert? If your partner doesn’t respect when you are a 10, it might not be a great fit.

Embrace positive reinforcement

Who doesn’t want to hear real, genuine compliments about themselves and their work? It helps if you have a business partner or collaborator who you truly admire (heyyy, Sara!). If you don’t, it might not be the best match. Don’t get crazy but do give real positive feedback as often as possible without it starting to feel pandering or insincere. On the flip side, don’t hesitate to ask for feedback. One day on a call, I felt discouraged because I felt like I had worked hard but didn’t get enough acknowledgment; like we had moved past my progress too quickly and on to the next thing. Instead of pouting, I directly asked Sara for acknowledgment of my work -- she gave it (in a genuine way) and we moved on with no hard feelings.

Say what you mean -- and accept the other person at face value

I try to make a conscious effort to not say phrases or words that I don’t mean. For example, if I say “I don’t care,” it’s because I genuinely am not invested in any outcome. I sometimes say to Sara “I don’t have an opinion, but I can if you want me to.” She knows that this is my way of saying “If you care a lot, go for it. I support your decision. If you want or need me to be in on the decision, I can do that, too.”

On the flip side of saying what you mean is accepting that the other person is doing the same -- taking them at face value. As you strengthen your partnership or collaboration, you may need to check in on this. For example, you might say to a collaborator: “I just wanted to confirm that when you say you don’t care, it really does mean you don’t care. Is that true?”

Share your feelings -- and don’t

Both Sara and I have initiated conversations about our hurt feelings, frustrations, and annoyances. On more than one occasion, we’ve talked through our feelings, listened to each other, and improved our relationship because of it. On the other hand, it’s also important to recognize that you don’t always need to bring up every little issue. I’m not advocating burying your feelings but if you’ve made a conscious decision that you can truly get over the issue and that it won’t be a continued point of soreness or conflict, I’m giving you permission to let it go. (Cue Frozen. Obviously.) Overtalking your feelings can be a slippery slope, so be aware of it and cultivate the ability to really, actually get over things. (This will serve you outside of business too, I promise.)

Default to each person’s expertise

You’re likely partnering with someone because their expertise complements yours. There may be a fair amount of overlap (I’m obviously picturing a Venn diagram), but I imagine you’ll both bring unique skill sets, ideas, and experience. Learn each person’s strengths and know when to default to that person. In our case, this doesn’t mean that I can’t have an opinion about punctuation and grammar just because Sara is a copywriter, but I may take less of a stand because of it (see "learn when to take a stand -- and when not to").

Know when to table stuff and walk away

In The Solopreneur Sanity Handbook, we talk at length about the value of proactive breaks to prevent burnout. In a partnership or collaboration, breaks are doubly important. Not only are you preventing your own meltdown, but you’re likely preventing tension with the other person. Begin to recognize the signs that you and your partner need to step away. In our case, we're both able to notice when our voices and body language change just slightly (yup, this comes across on video) -- enough to indicate that a proactive rest is critical.

Often, you can take a break and come back refreshed with a different perspective. This happened to me recently after a quick 5-minute meditation -- I decided the thing I was pushing wasn’t worth arguing over, so I articulated to Sara that I was laying it to rest.

Sometimes you’ll take a break and realize you can’t jump back into the same thing right now without tension. Acknowledge that, then move in a different direction.

My biggest takeaways from our partnership

Even the best partnerships come with challenges, but hey, we’re solopreneurs -- loving challenges is in our blood! I don’t think it’s any exaggeration to say that successfully navigating a partnership can make you a better person in all areas of your life. It makes you more self-aware, more willing to compromise, and propels you forward as a business owner.

A great partnership or collaboration can be like having a business coach, an accountabilibuddy, a friend, and a co-conspirator all in one. Who knew that two random chicks from different parts of the country with pretty different lives would come together via the internet to serve you, our One Woman Shops, and have a fun, rewarding, and dare I say, awesome partnership?

How can you capitalize on a collaboration within your business and how can you apply these tips to a relationship in your solopreneur life?

How (And Why) To Outsource Your Instagram Marketing

outsourcing for your solo business

outsourcing for your solo biz

I love being on Instagram. I love sharing my tips and ideas. I love interacting with people. I love searching through hashtags and finding awesome new people to follow.

(I also love shopping via Instagram -- which isn’t so great for my bank balance.)

What I don’t love is taking photos or creating graphics.

As a copywriter, I’m happy to admit photography and graphic design are not my strengths. Needless to say, I was wasting a lot of time trying to do it myself and still not getting the look and feel that I really wanted for my feed.

As soon as I could afford it, I outsourced my image creation and curation on Instagram. And it’s been an awesome decision.

In this post I’m going to share with you how I went about outsourcing my Instagram images and why I’m more in love with Instagram than ever.

How I went about outsourcing

As luck would have it, a client I was working with brought on a junior graphic designer to help me manage their Instagram feed. She’d curate images in line with the strategy and I would write the captions. It worked really well and their feed started exploding (in the good way).

I realised that I could do the same thing with my own feed, so I asked that graphic designer, Angelina, to work with me.

The first thing we did was sit down and discuss my Instagram strategy and branding. We then arranged a photoshoot to capture a bunch of images for my feed.

Now, at the start of each month, I send Angelina a list of tips, quotes, and brands I want to mention on my feed. She then curates images and creates graphics and puts the whole lot in a shared Google Drive folder.

All I need to do is grab the images, add captions and schedule them with ScheduGram.

The results of outsourcing

Now that I don’t have to worry about the visual stuff, I have more time to actually engage with my followers and create new content I think they’d love.

Of course, paying for something like this only makes sense if there’s a return on that investment.

And I have to admit, I was slow to see results at first.

But recently the engagement on my feed has taken off -- my email subscribers have grown, I’m getting copywriting enquiries directly via Instagram, and I’m even getting comments IRL from people about how helpful my feed is.

The big thing for me was ensuring that I maintained control over the content of my Instagram feed (I am a copywriter, after all). So I didn’t want to outsource the entire management of my Instagram feed. Every caption and comment is me.

How to outsource your Instagram marketing

Now, you might love creating images for Instagram, but maybe there’s another business task you’re doing that would make much more sense to outsource. If you’re thinking of outsourcing, here are my tips for making it work based off of my Insta experience:

Know what your objectives are

Make sure you know why you’re outsourcing a part of your business. For me, it was because I wanted to have an Instagram feed that felt branded and cohesive to help me find new clients.

For you, it might be to grow your engagement, give your brand a clearer “voice” or simply save time on something you don’t enjoy doing.

Figure out how much control you want to maintain

You might be happy to outsource all of your marketing, a part of it (the visuals or captions) or maybe only the stuff that followers wouldn’t notice (like ‘liking’ certain hashtags or finding new people to follow).

I would never get someone else to write my captions because I want my voice to come through, but you might be happy to let a copywriter who gets your brand to do it, while you take your own photos because maintaining control of your visual look is more important.

Do your research

When it comes to finding someone to outsource a part of your business to, spend some time looking for the right person. I was lucky that I’d previously worked with Angelina and already knew how well we worked together.

Seek out recommendations (Editor’s note: We highly recommend the ladies in the OWS Directory!) and take a look at what that person is doing on their own feed or for their clients. Ask them about their collaborative process and what they’d need from you to make it work.

The truth about outsourcing

A tip: As soon as you start investing in a part of your business, you start to take it a lot more seriously. Putting money into my Instagram has made me treat it as a key pillar of my marketing funnel, rather than just a fun place to hang out. And it’s definitely paid off for my business.

Would you ever outsource all or part of your Instagram marketing? If not, what would you outsource? Let me know in the comments below.

PS -- Not sure where to start in evaluating potential pros? Our Prior to the Hire ebook has you covered.

Prior to the Hire ebook from One Woman Shop

Is It Time to Outsource a Task? Ask Yourself These 3 Questions

outsourcing for your solo business

outsourcing for your solo biz

Editor’s note: We’re kicking off outsourcing month here at OWS! This post serves as a primer for deciding what tasks you might want to hire a pro to take on.

For many of us, we start our businesses out in bootstrapping mode.

You Google search. You consume blog post after blog post. You ask for advice in Facebook groups. Basically, you biz hack.

And even though this is more time consuming (and can be more frustrating) than turning to an expert, the DIY method does have some tangible benefits for a new business.

For one, it gives you as the biz owner a clear picture of what it takes to complete a task. (This is helpful intel to have when you do eventually hire support.) DIY-ing can also save you some cash in the short-term, something that is usually crucial for new business owners.

Let’s be honest, though. No matter how much of a well-oiled machine your one woman shop is, you’ll eventually need to call in reinforcements.

As your income streams diversify, you may no longer want to do your own bookkeeping. Maybe you'd like to hire a copywriter to really get that sales page converting. Or you might need a VA to get your newsletter off your plate and on a regular schedule.

Everyone will need support at some point. But how do you know when it’s the right time? How can you tell if your biz has hit that magic tipping point where your energy is better spent on other parts of your business? When I’m trying to make that call, I do a mini biz audit.

Here are the three questions I ask myself that help me know when it’s time to outsource a task:

1. Is it out of my zone of genius?

Does copywriting or web design stump you? Is it stopping you from expanding your biz? Could your time be better spent elsewhere?

No need to fret if you’re not great at a particular task. You’re good at what you do, so don’t be afraid to be honest with yourself about the things that keep getting pushed to the bottom of your to-do list. While yes, there’s a case for learning some skills (read more about how to evaluate where you invest in your education here), unloading the tasks you’re not suited for will free you up to better serve your clients.

2. Is it a have to and not a want to?

Are you capable of completing this task, but you simply don’t want to? Is it simple, but too time consuming? Does it light you up, or inspire an “ugh?”

If you don’t want to do it, then don’t! It’s important to build a business you love. Naturally, there are going to be tasks that you aren’t enamored with as a business owner, and it’s normal not to love every minute, but there’s no sense escaping the 9-5 and bravely launching into self-employment just to feel like every day is still a drag, right? So go ahead -- outsource that stuff, girl.

3. Is it necessary?

In other words, should you even be going after this at all? Or is it a dead end? A shiny object project? Should it be on a stop doing list?

In Good to Great, Jim Collins says that successful businesses should not just have to-do lists but stop doing lists. Some things just distract you from doing what you do best and they need to be cut out for your business to meet its goals and grow. IF it’s a “stop doing,” it might not even be worth outsourcing -- but you won’t know until you evaluate all of your tasks and activities by these parameters.

How did you answer the three questions above?

If you’ve found a task that’s out of your zone of genius, is a “have to” and not a “want to” and is absolutely necessary to your success, don’t be afraid to don the boss lady pants and consider outsourcing.

Get your mini biz audit on, and get outsourcing

It can be a scary thing to bring another person into this business you've built with your own two hands. But taking the time to reflect will really make you more confident that you're making a smart move -- one that could propel your business forward.

One Woman Shops: What have you considered outsourcing -- and what’s holding you back?

PS -- Outsourcing isn’t limited to “business tasks.” Why not outsource some of your personal life, too?