How to Tell If You Need to Hire a Bookkeeper

Photo by Phung Hi

In the early stages of running a business, it’s easy to get away with a hobbled together, spreadsheet-based bookkeeping system. But once your operation starts to expands, the financials tend to get more complicated or you have less time to manage all the administrative stuff. At that growing pain point, you’ll realize you’re in over your head and that it’s time to hire a professional bookkeeper.

There no set point that determines exactly when you should hire a bookkeeper. But the following symptoms will present themselves, making it more obvious that it’s time for you to bring on professional help.

You’re Always Behind on Your Bookkeeping

You’re always behind on your bookkeeping, so you never actually know the state of your business finances. It’s stressful and mildly infuriating that you don’t have this information. You’re discouraged from getting caught up because it feels like an impossible task. And if you’re never known the beautiful glory of not being behind, you can’t truly understand why this is important.

With proper bookkeeping, you know how much money your business made last month and all the months before it. You know how much your business spent and if you’re even making a profit. With a great bookkeeper, you receive your monthly financial reports on a regular basis.

Being and staying caught up on bookkeeping is literally a whole new world of clarity and understanding.

You’re Freaking Out At Tax Time

Tax season doesn’t have to be fraught with multiple, confused emails fired off from you to your accountant at 2 am. It also doesn’t have to be you printing out 200 pages of bank statements, using six different color highlighters and a calculator to figure out your profit and loss statement on your office floor. I promise you, it doesn’t have to be this way.

In fact, it should be a pretty smooth process. I know your accountant wants that too. Here’s how it should go down:

1. If you’re like most businesses, your accounting period will close along with the calendar year on December 31 and you close out your bookkeeping for the prior year sometime in January.

2. You send your financial reports and all your other tax documents to your accountant and they file your taxes for you.

3. If you owe taxes, you already knew you would because you were keeping your books all year long and you saved for taxes as you earned income. Or you get a refund, yay!

Tax season isn’t stressful if you go into it being prepared. And being prepared is something totally within your control.

Your Accountant Does Your Bookkeeping

You might think you’re a genius for forgoing monthly bookkeeping and having your accountant haphazardly put together your books right before tax time, but here are the pitfalls of this strategy:

1. You aren’t watching your business finances month to month, so any business decisions you’re making aren’t rooted in actual data. For example, can you really afford to hire someone? Or does it make sense to stop offering a particular service because it’s not as profitable as other services?

2. You’re probably spending more having your accountant do your bookkeeping since accountants tend to charge more per hour.

3. Your bookkeeping probably won’t be done in as much detail. This is fine, until it isn’t. Meaning, sometimes when you realize you need the data, you realize you don’t have it - like during a small business loan application or when you’re trying to understand the value of your business because you’re going to bring on a partner or investors.

What To Look For

So now that you know you need a bookkeeper, what are the qualities you should look for in a bookkeeper or bookkeeping firm?

Clear Communicators

A good bookkeeper can effectively communicate with your accountant and you. They should be able to explain your financials to you in plain language.

Accurate and Timely Delivery

You should be receiving your financial reports in a timely fashion so you can use the data to help you make decisions. A timely delivery is receiving your financial reports no more than two weeks after the close of the month. If you don’t receive reports for months at a time, you’re flying blind.

Your bookkeeper should work with you to make sure your reporting and categorization is accurate. They should make sure your bank balances match and they’re taking your accountants advice into consideration.

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When it’s time for you to upgrade your from DIY to a professional bookkeeping solution, check out our guide to help you understand your options.

How To Map Out Your Monthly Income Goals

Photo by Simon Migaj

My wife is a woman of many, many talents, but cooking is not one of them. I marvel that the same woman who is militant about being creative everyday is somehow baffled by the challenge of a freestyle kitchen session.

Besides her lack of interest in preparing food, I think the fact that she doesn’t spend time strategizing and coming up with a plan is a huge factor in her adversity to cooking. And we all know once you’re hungry, you’re no longer a rational person. You’re a shell of a human, hijacked by your emotions and panicked because your tiny brain thinks you aren’t going to survive.

This exact approach, or lack thereof, is how a frightening number of freelancers and small business owners approach the income side of their economic equation. If this is you, know that I’m not judging you nor am I throwing shade. Just realize that if you don’t spend the time strategizing and coming up with a game plan for your monthly income, you may find yourself becoming irrational, taking on weird jobs or working with less-than-ideal clients because you fly into a panic-induced survival mode.

This can set off a chain reaction of problems. For example, let’s say you agree to work for less than you should because you have no clue how much money you’re earning, you just know you need to earn money. And if you’re earning less, you’ll need to work more. And if you work more, you have less time to for the things that bring you joy. And with less joy in your life, you’re a bummer to be around. If you’re a bummer to be around, you don’t attract your ideal clients who can actually afford what you’re selling. And you’re trapped in this cycle.

When you allow yourself the time to project your income for the month (or months) ahead, you’re allowing yourself to have insights, to make plans for future growth or plans to slow down to keep a manageable pace. After you make the projections, you can observe the results. Which allows you to realize what’s working, what isn’t working, what predictions were right and which ones need to be refined. In other words, it’s a way more chill way to be, dudes. And yes, this is the method I use to make sure I’m on track with my business goals.

How Much Do You Need to Earn Each Month?

This is the first step; it’s the prequel. You have to first calculate how much you need to earn each month. A good place to start is to look at your expenses. How much does it cost you to stay alive on this lovely planet? And what are the other things you’d like to spend on each month? How many box subscriptions does one need to attain happiness and enlightenment? If you still to figure out how much you need to earn, here are some methods to go about doing so.

Make Time to Map It Out

Once you know your monthly income goal, you have to make time to see how close or far you are from that goal, given the information you have at the moment. For the sake of example, let’s say you need $4,000/month to live your best damn life. Here’s what you’ll do during your mapping session.

Pick Your Method. You can go analog with a pen and paper. You can use a fancy calendar app or a quick-and-dirty spreadsheet. Choose a method for mapping out that resonates with you. It’s helpful if it’s a method you feel comfortable using so you’ll keep using it. Set yourself up for success; don’t create barriers to doing the work you need to do.

Do The Math. Once you choose your method, make a list of how much money you know you’ll be earning for the month. List how you’ll be earning it. For example, you have 5 clients who committed to one-hour breakdance lessons at $100/hour. So, 5 hours x $100 = $500. And let’s also say your beautiful face is getting paid $2,500 to be a model for vegan, artisanal, shaving cream or something weird like that.

As of this mapping session, you expect to earn $3,000 ($500+ $2,500), which means you’re short of your monthly income goal by $1,000. If this is where you’re at, I can understand why you have avoided mapping out your revenue. It sucks to have a goal and not achieve it. So process those feels and let’s get on with figuring out a strategy.

Strategize. I think there might be a few options if you’re short of your goal.

Option 1. Learn to live on less. This is a totally viable and reasonable option. It’s all about living with the compromises and understanding the tradeoffs.

Option 2. Do nothing and have good luck and/or good timing. Possible, but maybe not probable?

Option 3. Do things that may help you earn more money. The following is a list of things you can do: Reach out to potential customers who might have previously expressed interest in working with you, try a new marketing channel, try a marketing campaign that makes you stand out, send out an email blast, change your pricing, change or repackage your offering, ask customers for referrals, put a product on sale, sell something you haven’t sold before, ask your friend who runs a popular website to feature you in an article, etc. There is a universe of possibilities here. Go on, get creative.

As an added incentive, knowing your deficit means you need to be specific about the amount of money you need to earn to close the gap. And being specific is perfect because it helps you discern what opportunities to say yes to. And oddly enough, sometimes when you aren’t specific, you fail to see opportunities.

And if you’re reaching your monthly income goal, that side of the coin has plenty of options to weigh as well. Should you keep things the status quo or scale back or raise your prices? Should you take a nap? The possibilities are endless.

Track Your Progress

It’s really easy to make predictions and forget about tracking or revisiting them, especially if you’re worried about not reaching your goal.

At Least Monthly

You should track your progress at least monthly, if not more frequently. Twice a month or once a week are both great time tables for assessment. Daily might be a little too crazy - unless you’re running a restaurant, in an specific industry or in a critical time where meeting daily goals can have a dramatic impact on the long-term survival of your company.

Know When To Change

If you’re consistently not meeting your goals, then think about changing something. The trouble is not just knowing when to change, but also what to change. Are your goals too lofty or are you not hanging on long enough to see true results? Can you move the needle in a meaningful way with small tweaks to your copy or do you need a new marketing strategy? Does one thing need to change or does everything need to change?

Listen, Reflect, Be Open

Remember fifth grade science when you learned the Scientific Method? Here’s a refresher: Make an observation, form a question, form a hypothesis, then conduct your experiment, observe the data, analyze and interpret it and come to a conclusion about your hypothesis. That is basically what I’m telling you to do, just through the lens of earning income.

So much of being a freelancer or running business is about experimenting. We have an idea about a problem that we can solve, we start figuring out how to solve it, how to speak to the people who will buy our solution, how to make adjustments to refine our offerings and reach our targets. Make sure to listen to the market and your customers and to be open that the answers are all around you.
 

How Much Money Do You Need to Make?

Knowing how much money you need to make is crucial when you’re thinking about or have just started your own business.

In theory it’s simple, but in practice it can be challenging.

It starts with understanding how much money you typically spend and save. And it takes into account how much you want to change your spending and saving.

Once you have a general range of how much you need, you can start to do things to impact the income number. Control the things you can control like investing in your company to earn more or cutting back on unnecessary expenses.  

If you don’t even have a target, it’s tough to know where to aim or how to make your chances of hitting the target better.

The first step to figuring how much money you need to make is knowing how much you need for your personal expenses.

Step 1. Get the Data Together

I come from the school of thought that the best way to figure out how much to budget is to track your expenses for three months. I use actual data as a basis because at least you’re starting from reality and not your beautiful and wonderful and robust imagination. (Read: I don’t trust that you know how much you spend on things like clothing or over-priced avocado toast).

Your first option is to pull the last three months of statements, use a calculator and spreadsheet.  It’s tedious but it’s accurate, but you can start now.

Another option is you can track expenses for the next three months using mint or personal capital or some other app out there. It’s less tedious and you push off being financially responsible for three beautiful months.

Another option you have is to use the bank’s technology to help you. Most banks compile a year-end summary or a year-end spending report. Download yours from last year. It might have inaccuracies because the bank’s AI machine thingy is doing it, but it might be a good place to start.

Put Together Your Budget

After you choose your method, download the data you need and get organizing.

Even if you use an app, I still like using a spreadsheet, obviously because I’m a dork, but I like the creative control I have over how I see the data.

Get Your Free Worksheet: Know Your Numbers

The first layer of expenses are fixed expenses. There are the bills and expenses you have that you are obligated to pay each month. So things like rent, utilities, groceries and any loan payments. I call this category fixed expenses, even though groceries can vary, they’re fixed because you must spend in this area every month.

The next layer of expenses are called discretionary. They’re things that you don’t necessarily need to spend on each month, but they make life better. Often it’s clothes, your hobbies, your vices and other fun, recreational stuff.

The third layer of expenses are what I call ancillary expenses. Think of these as expenses you’d cut if you had to go on a wartime budget because you’re pivoting your business and it’s slow or your company isn’t as profitable as you thought it would be. So things like putting away money into savings, investments and giving it away as charitable donations.

Sidebar: Taxes I add taxes into this category to because they’re a function of income. If you aren’t earning money, you don’t pay taxes. But taxes are unique snowflakes, they’re dependent on everyone’s unique situation. More on that later.

If you’re only looking at the last three months of expenses, don’t forget to add in things you might pay only once or twice a year like property taxes or insurance payments.

Whether you use a spreadsheet or an app or a website, get a monthly total and an annual total. If you get sticker shock because of how much you spent, maybe you should create a projected budget and modify some of the figures.

Adding in Business Costs

Next, figure out how much your business will cost you… to set it up.

If you haven’t started your business, how much are startup costs or pre-launching costs. Do you need to pay for a website and business cards? Do you need purchase $10,000 worth of Herbalife before you can start selling (please, don’t do that). Or do you need to buy a building and set it up to grow 100 lbs of cannabis because you want to start a cultivation center? Figure that number out.

Then, figure out how much it will cost you to run your business each month. What are your monthly bills? How much is your email service and all the apps you need? If you’re already running your business, then take a look at the last three months of expenses and figure out an average cost.

You can also look at a range of how much spent. For example, $25-50/month.

The safest bet could be to take the maximalist approach and assume you’ll spend the higher number each month. It can be scary to take the maximalist approach, but likely safer because you’re building fat into the budget.

You’ll have variable costs the way you do with your personal budget. Things like the costs of having coffee meetings or marketing expenses.

Don’t forget the one-time costs like paying your accountant or if you pay for annual subscriptions.

A little commercial about taxes. Disclaimer, Im not an accountant, so this isn’t tax advice. This is advice that you should get tax advice. If you have a pass-through entity, like an s-corp or LLC, your taxes might be limited to city taxes or sales taxes and not federal income taxes.

But remember what I said earlier? About taxes being unique snowflakes. Let’s look at an example. Let’s say Marion is a florist and he pays himself $46,000 from his s-corp. His company, Flowerz by Marion, ends up with a profit of $50,000 at the end of the year. Now let’s say Charlie runs a company that teaches little kids how to play golf, Putz by Charlie. And she also pays herself $46,000 in salary, but her LLC ends up with a $15,000 loss at the end of the year. Even if their salaries are the same, their companies financials vary.

What I’m trying to convey is that small business owners have an additional layer of tax complexity because with pass-through entities (s-corps and LLC’s) the net profits (or losses) flow through to the owner’s personal taxes.

So now you can figure out your business’ monthly and yearly expense.

Get Your Free Worksheet: Know Your Numbers

Figure Out How Much You Need to Earn

Now that you know that, I want you to breakdown how knowing your monthly number breaks down into income goals.

For example, once you realize you need to earn $8,000 to pay yourself and run your company, how can you frame that in regards to how you make money? If you charge $150/hour, then you’d need to bill about 54 hours a month to earn that income.

If you work on an $8,000 a month retainer, how many clients on retainer do you need each month?

After you make your income goal, it’s up to you to reflect on how realistic the goal is. Maybe you need to change your spending and pay yourself less or maybe you need to raise your rates so you don’t have to work crazy, long hours.

Get Your Free Worksheet: Know Your Numbers

A Totally Not-Boring Guide to Getting Your Financial Shit Together

Photo by Verne Ho

This is a beast of a checklist. It’s pretty high-level overview of the things you need to do, questions you need to answer and math problems you need to solve to feel like you've got control over your finances.

It’s going to take time. You might get stuck on the budget step for a while or on the figuring out how to make enough money to live your life step for a while.

You can do some of the steps concurrently, but you’ll see that it’s hard to jump around the list and make headway.

The contents of this checklist comes from an amalgamation of my formal education (s/o to everyone with a degree in finance) and my work experience in the years I was a financial planner, a small business consultant and how I work with folks currently.

Please realize that this is all total and absolutely nonsense, but it can help you feel a small sense of control in a universe of uncertainty; It can help you exist in the world we live in today, one that is governed so profoundly by economics and money.

1. What the hell do you want to do with your damn life? And how much will that cost you?

Figure out what the hell you want your life to be like. Am I asking you to create goals for yourself? Yes. Am I asking you to take a hard look at your life and to figure out what you want out of it? Yes.

Here are the questions you should ask yourself to help you figure out what the hell you should be doing to get your damn life together.

• What are your personal values?

• What are your personal goals?

• Map out your goals in terms of timeframe: short-term, intermediate, long-term.

• What are your business values?

• What are your business goals?

• Map out your goals in terms of timeframe: short-term, intermediate, long-term.

Not only am I asking you to explore the inner terrain of your damn self, I’m also going to make you turn that shit into a math equation.

• For your personal goals: breakdown your goals into dollar amounts. How much money does each goal need? Use the time frame to help you understand how much money you should save over time. For example, if you want to save $10,000 and you can save $500/month, that means you can reach your goal in 20 months. These figures might be arbitrary right now because you still don’t have a clear picture or other important aspects.

• For your business goals: breakdown your goals into dollar amounts. How much money does each goal need?

This breakdown will help you prioritize your goals and figure out which ones you can start moving towards. For example, maybe you think buying a house is a short-term goal, but the fact that you need to save $120,000 for a fucking downpayment might make you push it further to a long-term goal or maybe you’ll realize you ultimately value flexibility and you will decide to build equity and wealth in other ways.

2. Get Good At Earning Money

Now that you know what your goals are going to cost you, you may need to earn the money to make it happen.

Here are some questions you should ask and answer that will help you on your journey to stacking the cheese:

• What problem does your business/freelance work help solve? (If you work for an employer, what problems can you solve for your employer?)

• Who are you solving it for?

• Will those people pay you to solve their problem?

• Can your potential customers/actual customers afford to pay for what you’re offering?

• Is the price you’re charging a reflection of the value they’re getting? Is it too cheap?

3. Know Your Numbers

As you’re getting good at earning money, you should figure out how much you need to earn to live day-to-day, week-to-week, plus additional cash you need to stack for your silly goals. Here are the questions you need to ask yourself and answer to find out how much cash you need to be bringing in.

First, figure out how much do you personally need to live?

• Add up all your bills, monthly obligations, cash for spending on having a good life.

• Don’t forget to include savings and debt payments.

• Express that amount in terms of your business model. How many hours do you need to work, projects do you need to sign or milestones do you need to reach each month to fund your life?

Next, figure out how much your side hustle/business needs to earn to run.

• Add up all your business expenses. Don’t forget to include expenses that might happen in lump sum like insurance.

• Add in the amount you need to pay yourself (the first part of this exercise).

• Express that amount in terms of your business model. How many hours do you need to work, projects do you need to sign or milestones do you need to reach each month to fund your business?

• Taxes are also a variable. Talk to your accountant to help plan for this.

Figure out how you’ll keep your budget. Will you actively manage your budget or passively set up systems to protect you from overspending?

Finally, do a Reality Check: Can you realistically earn what you need to support the numbers? You might need to rework the numbers if it’s not realistic. Maybe you need to adjust savings goals for a longer term. Or maybe you need to do some Tony Robbins, voodoo magic shit to make your wild dreams come true.

4. Setup Your Savings

• First, fund your emergency fund. The general rule of thumb for an emergency fund is 3-6 months of your expenses. Make sure you’ve budgeted for this.

• Set up a high-yield savings account the bank you don’t have your checking account at (to protect yourself from yourself).

• If you can set up an automatic transfer each month or twice a month, do that. Get out of your own way. If not, then do it manually, but beware that robots are better at savings than you are.

• Figure out how much of a cash cushion you need in your business. The exact amount depends on the business, but 3-6 months of expenses is a good rule of thumb.

• Come up with a savings plan to reach your goal. You can set up your savings with the bank your business checking is at. Try to fund it regularly with an automatic deposit.

• NOTE: It’s uber important to save even if you’re in debt. So you might have to cut expenses to make this happen.

• Start saving for other goals in your life the way you do for your emergency fund: What’s the goal amount? What’s the deadline? How much will you save each month?

5. Get Your Shit Together (Get Organized)

The following checklist will help you tidy up your finances. You’ll feel great and you’ll great.  

• Make sure your checking accounts are only for spending and not for saving. Set up your emergency fund as a separate account from other savings like wedding or retirement or travel savings.

• Assuming you have the cash, pay your bills on time. Try setting aside time to look at your finances or making it a ritual, get booze involved, or just stop being a baby and handle your shit.

• Don’t forget about old 401(k)’s. Call HR and ask them where your damn money is. If you have money in an old 401(k), don’t forget about it and maybe even roll it over into a different retirement account.

• Keep your business and personal separate. Please, for the love of cute dogs, separate your side hustle from your personal accounts. Only business expenses and business income and paying yourself will happen with your business accounts. And everything you spend for personal stuff should be in the personal accounts.

• Start scoping out your business team: attorney, accountant, bookkeeper.

• Hire a great accountant.

• Understand when it makes sense to set up a proper entity so when you get there you know to set it up.

• Will using technology help you or make you less organized?

6. Make a Plan to Get Out of (High Interest) Debt

First ask yourself, how and why did you get into debt?

Next ask yourself, can you fundamentally alter the circumstances that got you into debt so you won’t get into debt again? Meaning, if it’s something like medical debt that you couldn’t foresee, then can you put systems in place to help you prepare in case something similar happens again?

Examine the options for getting out of debt and determine your plan. Options can include a loan from a rich friend or family member. Warning: there may be psychic or other types of non-monetary interest that you pay when you borrow money from someone you love.

Other options include a personal loan, negotiating with the credit card companies or starting a side hustle for extra income.

7. How to Care About the Long Run

You have to care about your future self because nobody else will. It’s sad, but it’s true. Here’s what you need to do.

• Understand that investing is magic and that cash can lose value over the long run, which is why we’ve been taught it’s important to invest. Then start actually investing.

• Your accountant can help you determine what type of retirement account you can and should open up.

• Learn about wealth and how you can build it, if you’re into that sort of thing.

• Make projections for how much money you’ll need in the future.

• First you might need a good cry when you see how much you need to save. The, start implementing a plan for your old self. Some examples include the following: getting a boring job selling insurance so you can earn money and save for retirement, planning to eat cat food in retirement, marrying someone rich. The options are endless, really.

• Stop not having a will and an advanced medical directive.

8. Love Thy Accountant

Get an accountant whose job is to learn the new tax code and help you navigate it when it comes to your unique tax situation. Here’s what your accountant might help with you:

• Figuring out all the types of taxes you’ll be responsible for

• Figuring out how you’ll pay for taxes

• Keeping you updated with important tax dates

• Ask around for accountant referrals, interview them and figure out if it’s a good fit.

9. Manage Your Risk

• Figure out what kinds of risks you’re exposed to and determine what risks you’ll outsource to insurance. For example, driving a car has a lot of risk, but you can outsource the risk by getting auto insurance.

• Understand what’s out there. In general there is health, auto, renters, homeowners, general liability, professional liability, disability and life.

• Determine what kind of insurance you need personally and professionally.

• Determine how much insurance you need.

• Gather quotes.

• Choose the insurance, buy the insurance, make sure the insurance policy covers what you need it to cover.

There you have it. The definitive guide to help you get your finances in order so you can live your damn life. If you’re more overwhelmed after reading the list, I’m sorry for the momentary discomfort. And you’re welcome for lighting the fire under your ass. Here are some pro tips to get through the list:

Pro Tip No. 1

Realize it might take time. Sometimes it takes years to master earning money or reaching a big savings goal. I feel you. I’m an impatient idiot about everything.

Pro Tip No. 2

Don’t beat yourself up. Control what you can, but realize there is a lot you can’t. What a fun ride life is, huh?