Ask an Anchor: How do I make progress toward my big goals?

Dear Sarah,

It’s been a busy season for me, which is great -- I know I’m fortunate to be working rather than scrambling to get by. 

While I’m busy with clients, tasks that I know are required (like keeping up with accounting, marketing/networking, sending pitches, keeping up with my industry) aren’t getting done. I’m SO EXHAUSTED at the end of each day and my weekends feel like precious recovery time, so I’m not willing to do some of this during those hours. Getting to these extracurriculars actually feels physically impossible, and my creative juices are definitely not flowing after long days and weeks.  

I know those tasks are directly linked with my plans/dreams for the future. How do I not lose my footing on the business AND continue to work toward big goals when I’m busy?

Thank you,

Busy But Worried

Dear Busy But Worried,

A quick fix is what we all want, but that approach isn’t sustainable, sufficiently systematic, or focused enough when applied to the marathon that is running a business. 

What seems to work best, instead, is carefully analyzing the root of our problems, and working to identify the core issues and motivations in our businesses and lives. In all things: lasting change requires thought, care, and skillful use of momentum.

I honestly love working ON my business. I love planning, mapping out money, figuring out what’s working and what isn’t. If I could swing it (and I hope that I can someday), I would do it all week long. It feels like a puzzle that’s solvable but also endless. Planning eases my anxiety, and it gives me real creative fuel for the next steps in my life and business. Knowing what you want and what to look out for in those decision-making moments is the best gift you can give yourself and your business. 

Focusing on developing your business will be the way your business grows. Is that enough motivation to make the time? 

I used to hope for short days (in my past, sadder life phases) and now all I want is endless energy and 40-hour days just so I can get it all done and do more - live this one short beautiful life to its fullest. 

The joy of planning my business also gets me into trouble. I can fall into a hole of “what if’s” and “who could they be” and “how to reach them” which, when I fall into that flow (which feels SO GOOD), can get in the way of the real work that needs to be done at the moment. Your current business (your clients, deadlines, product development, etc.) are absolutely a priority. My suggestion is to create a day a week (or a few days a month) that is set aside just for the more significant projects. This is harder than it sounds, of course. 

“Your audacious life goals are fabulous. We’re proud of you for having them. But it’s possible that those goals are designed to distract you from the thing that’s really frightening you—the shift in daily habits that would mean a reinvention of how you see yourself.”
— Seth Godin

Here’s what I do…

I am similar to you. By the end of the day, I am done done. The “end of the day” might not always be at the same time either. If I start work early, the end of my creative (and kindhearted) rope will run out about 8 hours later (and those 8 hours include midday breaks, so it really looks like 6 hours of work) I have in the past executed consistent, longer days and I’ve lived off of coffee to the detriment of my health. I don’t do that anymore. In fact, I build shorter billable hours with space for breaks because I am more efficient with rest and under a “deadline.” Most people are that way.

When I have “extracurricular” tasks, I do best when I build a very large chunk of time for them rather than trying to sprinkle those essential tasks throughout the day or week. Maybe it’s because I’m getting older or perhaps it’s because of what much research is starting to show: we humans aren’t actually good at multitasking. And that flow takes time to achieve, so don’t let anything silly (like notifications on your phone) steal your attention. 

Bookkeeping and financial planning need at least two hours a week if not every other week. Create systems to cut down that time and hire the right support to make sure you’re not messing up your bookkeeping system. This effort WILL save you time in the long run. Do not hide from understanding your business’s financial health. I look at my cash flow every day. I can’t keep it all straight in my head, so I built that tool to quell my anxiety so I can quickly return to work. 

Bigger projects like marketing strategy and planning should take you a few, deeply focused days. At the very least, block off 3-4 days on your calendar every quarter. If you can afford it, take yourself to a cabin for those few days with specific goals for completion. There’s no way around this process. The reason you’re not getting to this particular task is that you’re not setting aside enough time to be a human. Humanity with a project like this means you need support in planning (other humans), time to tap into your creativity (long walks, hikes, swims), alone time and rounding it out with real action items. 

Write out the steps, figure out how long each one might take, calendar the steps, and go from there. The big picture work can be more ambiguous, overwhelming, or even not as rewarding in the short term. But your past (and future!) self are rooting for Present Day You to step up and chip away at long-term goals. 



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Ask an Anchor: Can we get un-stuck? My partner’s business partners won’t let me work.

Hi Sarah, 

I am an artist and illustrator who has dabbled in graphic design and home design. I am up to date on design trends and run my own business. My partner recently started a brewery with his brother and a third partner who was brought in to help with the financial end. The two brothers have always had a fun, creative vision, and I was never worried about the taproom design or logo process until we actually got down to it. 

Initially, I wanted to help with both logo and taproom design as I was confident that I could turn their personalities and spirit of brewing into visuals. I soon came to realize that these three men all have very strong, differing opinions on the ‘look’ they want. The challenge is that they could not verbalize their desires and could not come to unanimous conclusions. Getting to the bottom of visual work with one person is difficult, but with three, it is impossible. 

This has been going on for months. I’ve tried different ways to hone in on the process, including making a ‘lookbook’ and meeting one-on-one. Generally, I feel that they should be giving a designer (either me or a professional) the trust and respect to pick what he/she knows would work best for the business (not necessarily what they like, but what the customer would like). Projects are either on hold due to disputes or settled in the middle (resulting in a flat, boring look, including their logo). 

It is clear to me that my personal proximity to these people means they are not likely to treat me as a professional, but if this is the case, how do I convince them of the importance of hiring a professional (especially for the logo). It is also clear that a lack of communication between the 3 guys is a huge problem, they each have very different personalities. I also feel that the brothers could work it all out, but the third person seems to upset the balance. I would love to step back and let someone else work with these guys because I care too much to let them fail over lack of design consideration. I mean their product really is fantastic! 

Thanks so much for any advice you can give. 


The Fourth Wheel

Dear Fourth Wheel,

Business partnerships are complicated. I commend you for putting yourself right in the thick of it and caring so much to help your partner and their team find solutions. 

It sounds like these are all first-time entrepreneurs. Whether or not that’s true doesn’t matter much in regards to what I’m about to say: If they cannot move forward with this simple task and learn to let go of their ego, embrace imperfection, compromise and prioritize the business’ best interests (i.e., their customers), they will fail before they even begin. If the team cannot figure out how to divide and conquer, they will find this exact complication at every single turn in the business, and that kind of distraction will lead to failure.  

I firmly believe in the power of graphic design, but it will never be as important as the product. 

Branding is significant, but it will not make or break this venture [I will now hide under the desk as all designers fling their keyboards at me!] Initial customers will come to you based on the look of the product, but if you don’t deliver on your promise, no matter if it’s quality beer or perfect design assets, you will not survive. I assume they won’t and cannot compete by price, no one can really compete with the commoditization of big industry beer. So they are going to have to lean on the few assets they have within their control: quality and variation of the product, sales strategy, internal systems for foundational strength, customer service, an intimate understanding of profit margins, and last and least: design. All of the actual core aspects of business take much more effort, thought, and fear. Which is why people like to take their anxiety out on the “brand” and design.

In my business’ case, I spent the first two years growing Anchor & Orbit with only a splash page that contained a brief bio and a simple contact form. What really grew my business? I honed my skills, worked hard along the way, delivered beyond expectations, and after that, my clients wanted me to be successful, so the referrals rolled in. Eventually, when I did “brand,” the goals I outlined for the designer  were as follows: accessible, warm colors, create a sense of experience and have the layout feel like you were talking to a friend about your business’ needs. Outside of that, I let the designer run with anything she felt was best. And guess what? It worked. I let her be the expert to create something that (still) stands out from the crowd while being wholly relatable. She did the work, research, and implementation, and I asked for very few revisions. If I tried to create a brand for myself, I would still be working on my website now, three years later. She worked for my company’s vision and what my clients wanted from me, but not for me. I highly recommend all designers give this gift of creativity and expertise to their clients. But that’s another blog post (or book) altogether.  

What does branding do? A brand and good design will get people in the door (and their attention) and helps you gain industry respect. But, if your product speaks for itself, then the branding will not matter in the long run. The opposite is true as well - there are plenty of garbage products and businesses out there with great brands. You know when you meet someone really beautiful, but their personality sucks? Are they as attractive once you figure out their dirty secret?

In regards to beer, I’ve done my fair share of research by proximity. I’ve visited some kind of beer establishment most cities I pass through. Across the board, the brand and design of the taproom never indicate whether or not the beer will be delicious. But! Good branding and beautiful space will help us make a choice between two places. So, if you’re simply using me as a case study, you and your partner are fighting the good fight.

Here’s the real deal: I fear that the “brand” problem is code for a bad situation. 

And that this team is stuck in this conflict and that they’re having a hard time moving forward in this simple task are worrisome signs. I have something to say about this third partner who is there to help with the ”financial side” but seems to hold up decisions: get rid of him. He signed on to take what the visionaries have created and leverage their financial assets to help them succeed. He needs to step back and let them work, or he needs to leave. I fear that this “CFO” will always be the “nay-sayer” and with that, the business will struggle for its entire existence with him in it. Severing a business relationship once the company is up and running (and making money) is SO MUCH MORE costly than cutting ties early on, even if it slows things down temporarily. Long ago, a mentor taught me that “those who seek control lack talent.” Take a beat - think about that statement for a second. It seems that this third person needs to enforce their power, just to have a voice, even when it’s not the best move for the business. Considering all business problems, this is an easy one, so imagine this dynamic when there is a real challenge in front of them. Each person on that small, essential team should do everything in their power to push this project forward, not slow it down.

Those who seek control lack talent.

As for you, Fourth Wheel, you may have to step away to be the business owner’s partner and not the designer. Whether they are saying it or not, they might be trying not to offend you if they don’t like the direction. This could be the case even if you have stated that you can take the criticism and also if you are objectively correct about the design choices you’re presenting. I don’t think you’re the reason this project is sputtering, but I’m not sure you’re helping either. I do understand the fantasy of working with your partner and saying that it was a full-on family project. So, lead by example! Step away to let them work. As you know, there’s a shift in people’s psyche when they pay “an expert.” Expect a fire in their bellies to not to drag it out forever because, money.

If and when they move forward, I have one last bit of advice to help them in their long term success: each person must have their own role or “department” and once in that role, they must be trusted and in charge of their tasks. For example, if they are staying on-trend, they will want to change their labels and alter branding with every new release of seasonal beer. To do this, one person must be in charge of guiding the graphic designer. They can have a voting system and guidance about the vision from the team, but ultimately, final decisions need to come from one person. It’ll be the same when they assign who is in charge of their financials, sales, brewing, distribution, and employee management (to name a few).

No matter how much they like each other, especially the brothers, if they continually negotiate small decisions rather than assigning specialties and trusting in the others’ abilities, they are in for a long, resentful relationship - in and out of the taproom.


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Ask an Anchor: How do I handle my inconsistent income?

Hi Sarah,

I have a lot going well in my business, but I know that I'm missing things when it comes to my finances and accounting. Whenever I focus on the money, I feel out of my depth. 

Part of my issue is that my income is so inconsistent month-to-month, some advice about money doesn't feel like it applies to me. I often feel alone and like I’m having to make all of this up by myself. How can I set something up that works for me -- not a generic business?

Thank you!

Atypical Money Concerns

Dear Atypical Money Concerns, 

Ah yes. The old “is there a way to predict the future” question. I LOVE this question. It means you’re doing this right. You want to understand how your business is functioning, and how to strategically think about your business from a financial standpoint.  

You've outlined what most business owners, and people in general, feel all the time: like they're in the dark and they're not doing “it” right (whatever that “it” is).

The quick answer is you’re right! There isn't a specific formula that will work for everyone across the board. Not because there aren’t templates or age-old spreadsheets, but because each person learns and digests information differently. 

Just remember that there are tools you can implement to create a system that makes you feel comfortable and in control. If this is the last sentence you read, please read it carefully: You want to understand the reality of your spending (look back a few months and start to see your patterns), and you want to know what your earning potential (or actuality) is. Inflow, outflow and the balance of money after. 

Managing money is a very tender subject. 

Unless you were extremely fortunate, you were probably not taught about the strategies of having, saving, and increasing the value of the money you have on hand. I am not always great at managing my own money (business money is on lockdown, but personally, it's still a struggle to make sure I'm buying want I need, not just what I want.) I have debt (starting a business is complicated), I've struggled with cash flow (tough lessons in my own value), and I've spent money that I shouldn't have (damn you beautiful shirts by independent makers!) This truth needs to be out in the open because I want you to know that you're not alone. The struggle with understanding your relationship with money goes deep into one's relationship with their parents and their parent's relationship with money and … you get the point. You CAN heal your relationship with money, and you can be good at managing it -- it just takes a little rewiring.

I am not a financial adviser (that's a certification and degree), but I am a teacher who believes in presenting information in as many ways as possible when it comes to money. The reason I now understand how money works in business is that I studied entrepreneurship and applied those principles to my life. Theory and practice have a tendency to be hugely different, so I used that foundation of knowledge and remained flexible in the reality of business situations. From there, I created my own theories and systems to teach money understanding. 

What I know for sure: Even if you have a perfect brand or product or marketing campaign, without understanding what your money is doing, you're going to feel stuck forever. We ALL feel out of our depth sometimes. There is so much to understand. I encourage you to talk to an investment adviser and join a credit union that will help you open a 401k, IRA, HSA, and more. Prioritize those, and everything else will start to make more sense. 

To answer some of your questions … 

#1: Valuing your work 

What kind of product are you giving your clients? For example, are you creating a brand that will propel them to the next level, i.e., make them more money? Or will what you're doing level up your company and theirs at the same time? Consider the VALUE of your work in the present and in the future. Ask your clients about their own financial goals in regards to the value that you're creating for them. Read “Breaking the Time Barrier” by the Freshbooks team. It broke my brain in the best way. 

#2: Understanding what you NEED (and want) 

Listen carefully - you deserve all of the good that life can bring, including your dream income and the security (and fun!) that comes along with it. Taking time to understand your value can trigger a conversation about how much time you actually have available but MOST importantly it *should* bring up the question: “What do I actually need?” I highly encourage you to look at what you spend on a weekly, monthly, and yearly basis and make decisions based on that reality. 

#3 Solving inconsistent income

Some say the solution for inconsistent income is to create consistent income -- I agree! Find ways to create a baseline income so you can, well, enjoy yourself. Anticipating what type of income month or quarter you're having to help you pitch and look for work is one way toward consistency. 

Inconsistent income can also be a blessing! I also think that inconsistency is the way that this whole independent business game works. The freelance community is growing every day -- people are realizing the value of owning their time, finding atypical mentors, shifting their careers, and of course, motivating themselves outside of a boss/employee relationship. I agree with where your question was going -- to make this fun, we need a sense of control.

#4: Building control & consistency through spreadsheets

To create some sense of control and consistency, I would suggest you start a cash flow spreadsheet for yourself. Before doing that, hone in on your assignment above (#2), which is to understand what you need to make. Some grit is required here, especially if you need to make a certain amount of money to survive (i.e., no one else is supporting you.) I have always made sure to find a way to pay rent and all of my expenses every month. In the beginning, it was babysitting in the afternoons after seeing my first few clients. That side hustle to supplement my passion was a lifesaver, but once it got in the way of having more clients, I kicked it to the curb. 

Cash flow is the act of money going in and out of your business (it's quite a literal term.) Your cash flow includes the money that you want to set aside for taxes and potentially a little profit to start building your nest egg. Tax savings should be at least 25% and if you can afford it, 30%. If you have to pay less than what you've set aside, yay! You get to give yourself a bonus.  

I hope the above inspires you to talk about money and dive deeply into creating systems and plans that make you feel most comfortable. 

If you want to take a close look at your cash flow, I’ve created the Cash Flow Cleanse -- a new kind of money workshop for business owners. The next workshop starts on August 22 and I’d love it if you joined us.


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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.)