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

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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,


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! 


Do you have a question? Ask!


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Dear Sarah: Partnerships (and those around them)

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 and I’ve tried all sorts of 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). All projects have been either been put on hold for later 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 seriously throw off 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 amazing!

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.  

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!] I firmly believe in the power of graphic design, but it is not as important as the product. Initial customers will come to you when the look of the product is on point, 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 zero 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 who is 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. My partner loves beer &  breweries, and we visit some kind of beer establishment in every city we pass through on our many road trips. It’s a favorite past time of ours, and I am sure you know what I’m talking about even if no one else does. *high five, friend* Across the board the brand and design of the tap room never indicates whether or not the beer will be good. But! Good branding and a 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. 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 get in the way of decisions: get rid of him. That person signed on as a support role; 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 business 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. On the spectrum of problems, this is an easy one, so imagine this dynamic when there is a truly tough problem 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.

As for you, Fourth Wheel,  it’s possible that you will 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 to not 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 even 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 tap room.

Dear Sarah: Handling Cashflow

Hi Sarah,

I have a lot of things 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 and also worry that I'm undervaluing myself.

Part of my issue is that my income is so inconsistent (I don't make the same amount each month), some advice about money just doesn't seem to apply to me. So 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?

How do I get control (i.e., not feel so anxious when I meet with my accountant) when clients need a lot from me and life happens unexpectedly?

Thank you!
Money Concerns

Dear Money Concerns,

I have so much to say on this subject, and I will try my best to stay focused on your questions rather than wax poetic about what money (or not having money) feels like. 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 “it” is. The quick answer is that there isn’t a specific formula that will work for everyone across the board, but 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 understand your patterns), and you want to know what your earning potential (or actuality) is. Inflow, outflow and the balance of money after.

I am not always great at managing my own money (business money is on lockdown, but personally, it’s always 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 beautiful independent makers!) This truth needs to be out in the open because people don’t always go there in a real way and 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. So like anything else, you CAN heal your relationship with money, and you can be good at it -- it just takes a little rewiring.

I am not technically a financial adviser (that’s a certification and degree), but I am definitely a teacher that 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. That was all a long answer to your “out of depth” comment, which is -- we ALL feel out of our depth. 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 answers some of your questions …

#1: Understanding what you need to make (this is in regards to “undervaluing” yourself)

What kind of product are you giving your clients? For example, are you creating a brand that will propel them to the next level, ie, 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. Consider asking 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: 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. But I also think that inconsistency is the way that this whole game works. To anticipate what type of income month or quarter you’re having to help you pitch and look for work that fits best for you. Inconsistent income can be a blessing! 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 do agree with where your question was going - to make this fun, there has to be some sense of control.

#3: Build control and consistency through spreadsheets

To create some sense of control and consistency, I would suggest you create some kind of cash flow spreadsheet for yourself.  This means that you will want to hone in on your first assignment above, which is to understand what you need to make. There’s some grit that’s required here especially if you are of the kind that needs 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 life saver, but once it got in the way of having more clients, I kicked it to the curb ASAP. My point is that I know you will find a way to cover all of your expenses, but I know you’re talking about something else.  

Cashflow is literally that - the act of money going in and out of your business. Including the money that you want to set aside for taxes & 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.

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