Ask an Anchor: How do you take time off?

Somewhere aspirational

Somewhere aspirational

Hiya Sarah,

I’m thinking about having a big out of office moment the week of Christmas and the week after—going dark (no posts on social or on my site).

Am I nuts? Have you ever done anything like that?

Out of Office

Dear OOO,

First, a little tough love: You will never feel entirely prepared to step away from your business. The good news is that this gives you permission to stop waiting to be ready and get your vacation on the calendar and flights booked ASAP. While you’re at it, also add to your calendar the day when you need to start preparing for your time away and block off at least two days upon your return. More on the vacation-prep/recovery logistics a little later.

In general, I have absolutely gone entirely dark on social media. In fact, I focus very little on real-time marketing via social media, so I go dark ... a lot. It’s stepping away from my email that is most challenging. A client can need something last minute or (eek!) I forget that I promised a deliverable, so I depend on my email to give me that healthy boost of anxiety. 

Because email is my primary source of communication, I’m tethered to it if I don’t manage myself and my clients/business well. I’ll give you a few examples of how I prepare for a vacation that can help you formulate a plan for your much needed holiday. I have finally figured out that to go on vacation, I may have to work double shifts, handling the work that’s on my plate now AND trying to prepare for the work that might come the week I’m away. 

Here’s the general and somewhat unhelpful advice: “Manage your time better, then taking vacations will be easy!” Slow clap and an eye roll, right? 

There are (and will continue to be) moments in your business when you simply have to suck it up and be “heads down and focused.” This may look like working after dinner or on weekends. If you're somewhat opposed to the hustle, hustle, hustle entrepreneur mantra, this way of working isn't what you're aiming for or enjoy. So when it hits, remind yourself it’s just for a short time and for a reason (i.e. taking a vacation!) Make sure the hustle period actually is temporary, and learn how you can recover. Running a business is a marathon, not a 100m dash, and recovery is part of being a good runner (I love metaphors.)

When my work starts to dig into my overall wellness, that’s when I know that stepping away isn’t just important, it’s a requirement.

I have to take care of my most valuable asset — ME (my brain & my body.) Especially if you’re the primary (or only) point person in your company, tending to yourself is a necessity. There’s a lot of self-care that can happen day-to-day, but there’s something unique about shutting everything down (or as close to it as possible) for a week or two.

Side note: Those of you who aren’t prepping for a vacation can also use the checklist below for a weekly or monthly business health check-in.

I’ve tried to “bring my work” on vacation throughout my life. During school, I always promised myself I would study “at the beach/hotel/between meals.” This never resulted in studying and always ruined my time away. I was either riddled with guilt when I wasn’t studying, or when I wasn’t with my family, partner, or friends. I’m sure you can relate to “just 30 minutes of checking email” turning into three hours. Wouldn’t you rather avoid family vacation time by getting a facial or taking yourself on a solo hike? I know I would.

As a business owner who can “work anywhere,” I deeply prefer NOT to work anywhere. I like my desk, my routine, and my time away. I’ve learned that having a shorter, but actual, vacation is better than slipping in work here or there on a longer one. That said, I do love working on a plane - there’s something delightful about a built-in deadline, white noise and the rare, but satisfying Diet Coke. I know I’m not alone in this. Build me an office on a plane, and I’ll take over the world. ANYWAY… 

To take my vacation, I first create a list of things that have to get done before leaving.

Logical? Yes. Easy? No. Here’s a cheat sheet.

For clients: 

  • List each client 

  • Create a sub-list of tasks you owe them 

  • Communicate your vacation days 1 month ahead

  • Ask them if they’d like anything else from you before you go offline 


  • Send a reminder 2 weeks before you’re offline 

  • Send one more “goodbye” email the night before you are offline - invite them to send you emails w/ subject line rules: 

    • [URGENT] or [ASAP] - only for true emergencies, which you should define for them 

    • [AFTER VACATION RESPONSE] - self-explanatory 

    • [NO RESPONSE NEEDED] - self-explanatory 

For social media: 

  • Invite someone to “take over” your ‘gram 

  • Set up automated posts for each day you want to engage

  • Let people know that you’re offline, but will respond to their comments and DMs when you’re back 

For your business: 

  • You should have a list of weekly or monthly tasks that you like to complete

  • Look at the list and decide how many tasks you can do early during the vacation prep time

  • If you can’t prep (i.e., bookkeeping is time-sensitive... You can’t categorize your expenses or income until they happen) MAKE SURE THAT WHEN YOU RETURN, YOU HAVE A FEW DAYS DESIGNATED FOR JUST ADMINISTRATIVE CATCH-UP

Ok, that last sentence deserves its own subsection: Do you want to ruin your much-needed vacation? Then jump right back into work as soon as you get home. Want to relish in your vacation epiphanies and relaxed shoulders? Schedule a few days between your arrival back into the real world and telling people that you’re home. 

Another option: Hire temporary help

I had a client who desperately needed and booked a month-long vacation with her partner. This was a life or death type of thing: her marriage needed some tending to. 

Being online was not. an. option. We decided it was worth paying someone weekly to monitor my client’s inbox and send my client a single weekly overview email with any responses that needed more information. 

That assistant was able to respond in real-time and, if it truly was an emergency, would send a text to my client asking for her input. 

Nothing burned down that week, but there were some emergencies that their system handled beautifully.  

Amid all of this, hold onto the most persuasive business reasons why you should take a vacation:

The time away helps you see the big picture and identify ways you can manage your time on a daily and weekly basis, so you feel more at ease. This may also mean that you have to adjust your rate and create more value for yourself (and that's a perfectly wonderful thing.)



Ask an Anchor: How do I send non-sales-y cold emails?


Hi Sarah, 

I finally took the plunge, and I am officially freelance full-time. The clients who were once my side hustle are now my full focus. It’s scary, but I’m enjoying the freedom and the clarity of not being so scattered.

I know that some of the ongoing client work will keep me afloat, but I am hoping to create some kind of pipeline or, better yet, a financial buffer so if my client relationships change, I’ll be prepared. 

Here is my question: I know I have to start marketing myself, specifically doing outreach. This is totally new for me, and I am really struggling. How do I start doing outreach without being too sales-y? Help!  

Thank you, 

Resistant but Persistent 

Resistant but Persistent, 

Woah! Huge congratulations to you! The world of freelance is lucky to have you. You have your head on straight and know what you need to make this work. 

Toggling between the work you do every day and the work that keeps your business running is one of the most challenging parts about being independent, whether it’s freelance, small business, entrepreneurship, or whatever you’d like to call yourself. 

In regards to being too sales-y: 

Let this fear go. You have to talk about yourself and what you do in order to get work. But the key is that the people who are hiring don’t care who you are per se - they are already short on time and are looking for help. They only care about what you can do for them (and that you’re not going to steal their money). When you get them on the line, it’s your job to understand who they are and what they need. 

Ask them questions about their business to clarify your understanding of what they might need, and tell them how you’re going to help. 

Bad sales tactics are when you promise too much or (the worst offense) pressure people into saying “yes.” Tell the truth about what you can do and clients will respond to that. 

Get these potential clients on the phone quickly, actively listen, tell them what you can (and can’t) do. Send a proposal as soon as you can (or if you’re swamped, tell them when they can expect it and send it on time.) If they are ready to move forward, send the contract and invoice quickly. Once they’re in and saying yes, get the paperwork done and the deposit in motion. Even those who are ready and willing have a tendency to back out, so lock them in and get started. 

Setting realistic expectations and delivering above and beyond will help you with your future sales cycle in a big way. Happy clients lead to happy referrals. 

I know you’re asking about cold emails to potential clients, but I look at businesses holistically, so I need to make sure you have a few more things in order before we move on. The following list is very basic, but will really help you. When it comes to professionalism, which is what clients are looking for, this is essential for a new freelancer.  

Consider some of these assets:  

  • Website / Social / Marketing - nothing fancy, but if you can afford design and some customization, it makes a big difference in the eyes of clients who, frankly, don’t know who the eff you are. Testimonials of any kind are gold. Simple social media effort works, and so does consistent and targeted outreach.

  • PDF overview of your work - when we talk about cold emails, I’ll reference this. Clicking on an attachment in an email keeps people in their inboxes (not distracted) AND is a quick peek to prove you’re as talented as you say you are.

  • Systems - contracts, payment terms, delivery time, will all be something your client will ask you about so have those answers ready.

  • Work hours/response times - boundaries will save your life. Decide how you want your week to look and don’t forget to build in some lunchtime, times to move your body, and times when you are not looking at a screen.


The Cold Email

In my experience, and because of the nature of my work, cold emails have nearly never worked. But that’s just me! When people are ready to work with me, they’re looking for my services and find me by asking their friends and searching for articles. 

If they aren’t ready and looking, the concept of working with a business consultant is too new (or cold) to even try to pitch. What has worked is my happy clients talking about the solid work I do with other people. When those referrals come my way, I make sure I have all of the assets I listed above ready to go.

Whatever your business is, do take into consideration how your customer wants to find you. For example, if I grow my services to be more workshop based for bigger companies, I think cold emails will end up being a massive part of building that aspect of my business. What's working now is getting a warm introduction from my network to companies or people I want to work with. 

(Sidebar! We can talk about retainer clients another time because long-term contracts are also going to be a huge part of how to stay sane and cash flow positive)

Ok ok. The cold email. The below outline should be three short paragraphs with a closing line AT MOST. 

Get a warm introduction if you can, then...

  1. A simple headline, like “Copywriter looking to work with [Insert Company Name]”

  2. Keep it short
    > Brief introduction
    > Tell them how you’re going to improve their business
    > Tell them about your services and expertise

  3. Link out to your website AND include a PDF of your services and expertise (it might seem redundant, but think of it as thorough instead.)

Upon response:  Create another short email and include a link to book a call with you. This system is a HUGE time (and fumble) saver.  Calendly is excellent, but I know there are a few other services that will help people book you automatically. Assume your client is busy — make their life easier from the get-go. 

And have fun! 


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Ask an Anchor: Why am I daydreaming about a 9-5 job?

Photo by  Noah Buscher  on  Unsplash
I NEVER thought I’d daydream about working 9-5 for someone else. NEVER! But that’s often where my thoughts go these days.

Hi Sarah!

2019 has been ROUGH for me, to be quite honest. I'm on a rollercoaster of wanting to drop everything and quit, but then psyching myself up and pushing forward with my business. I NEVER thought I'd daydream about working 9-5 for someone else. NEVER! But that's often where my thoughts go.

I can't throw in the towel without at least trying to set myself up for success though, I know that. I want to understand my money and get my goals in line.

I have a feeling that the doubts that make me want to set everything up in flames might see themselves to the door once I can see where I'm going.

Thank you!

Conflicted in California 

 Dear Conflicted,

Let's talk about a real problem with the internet's fascination with business ownership. I like to call it: Entrepreneurship Porn. It usually looks something like this…

  • Go out on your own and immediately make six figures

  • Have the perfect branding

  • Obtain the "right" $300 clogs

  • Curate (and afford) the perfect living space

  • Get perfect photos of yourself

  • Also, have babies

  • Feel entirely OK with ambiguity

Easy as that! You're running a successful business!

This whole scene is well-intended, but a farce. And I know from talking to tons of business owners each month that it's causing severe anxiety and sadness. Overall, without real context, the above picture of entrepreneurship leaves people feeling one step behind, always.

Just like embracing real bodies, there is a movement surfacing that is helping us see the effort, pitfalls, and emotional turmoil that come with going out on your own. My work,internally and externally, is to help normalize the path of business ownership, which CAN lead to success. But first, the struggle, learning curve, and the reality of the dream. Have you figured out by now that the struggle is perfectly normal?

What it really takes to run a successful business:

  • Be an expert in your craft or service FIRST

  • Understand marketing

  • Believe customer service is of the utmost importance

  • Be financially literate and savvy

  • Also if you'd like to scale, know how to manage a team

  • Don't forget about that big picture thinking!

  • Also! Remember your family and friends and maybe take a vacation every once in a while.

Frankly, after juggling all of the above (of which I have left out A LOT), sometimes people DO choose to work for someone else. I consider that decision a "win" in and of itself.

A win? HOW? Running your own business is "the dream," right??

If the formula and track seem awful/hard/unappealing, a realization that you don't want to do "all of the above" will save you years of hardship. By uncovering the difficult truth of what it means to be a business owner, you will not only save money but stress & anxiety, which we know cause long-term health problems.

That all being said, I LOVE THAT WHOLE LIST. I LOVE RUNNING MY BUSINESS. I believe wholeheartedly that small businesses are the future. I support and teach them! Small business' success = my success!

Back to you, dear writer — I honestly don't think you're in the "shift back to 9-5 work" category just yet.

The folklore / rule of thumb is that it takes 3 years to reach "profitability," whatever the heck that means. For me, because of my low overhead, my business was "profitable" from the get-go… but that doesn't mean I was making enough to do essential things like save for emergencies or contribute to an IRA (or pay for all of my groceries). To afford the important extras, it took 4 years. Even now, during my 6th year, it's still a lot of work to maintain the income I genuinely need to feel great about keeping my doors open.

So why do I do it? And why should you keep doing it? Find ways to like all of the work. From doing your "craft" to figuring out a growth strategy.

Here are questions you can ask yourself as you start to envision the future:

  • What do I do the best inside of my business?

  • What can I hand off? And/or …

  • Do I have the means or trajectory to hire the right support who can take on the parts I don't enjoy?

  • Can I pay myself enough so I can do more than just survive?

  • Are there success points outside of income?

The category you could be in is one where you need to take a bit of pressure off of your "business" so you can actually focus on it. The pressure usually comes from financial responsibility, learned money fears from your upbringing, or (better yet) the perception of what you should be making.

Let's talk about internal vs. external motivations:

Connecting success with money will always leave you feeling, well, poor. Connecting success with real milestones and achieving creative goals will always be more fulfilling. The true nature of our patriarchal, capitalist society requires you to have money, not just now but later, to make sure that in your twilight years, you're taken care of. If we had a system that supported our health and well-being, we would have a lot more art, less stress, and maybe even world peace. Who knows.

I recently shared my cash flow with one of my lovely "assistants" (let's be real, they're my bosses.) I think they were surprised by what they thought my business looked like vs. the reality. The cash flow is tight, but there's also excellent work on the horizon. Numbers don't lie, but they also don't tell the whole story.

The money will always come and go. There are strategies, but mostly it takes longer to acquire than we hope and keeping it takes a lot of self-discipline. Continuing to pursue your business in a strategic and not-hemorrhaging-money type of way looks different than the stereotype of entrepreneurial success. I want to get you used to the idea that running a business is an energy, not a path to happiness or fulfillment. Overall, though, it can and should be a path to security and comfort.

Sending all the virtual hugs,