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37 Lessons From 5 Years of “Being My Own Boss”

Five years ago I took a huge risk–I left a comfortable job at a mid-size law firm in Kansas City. Since then, I started and sold a law firm marketing company, grown Venture Legal into a sustainable law firm, and started Contract Canvas (a digital contract platform for freelancers). My wife and I also welcomed two daughters into the world.

It’s been a rollercoaster. The highs are very high. The lows are very low.

But there’s one constant: more often than not, I wake up excited for what I’m about to do that day.

I don’t claim to have all the answers, but I’ve certainly learned a lot about entrepreneurship (and life in general) in these five years. So without further ado, here are 37 things I’ve learned since becoming my own boss.

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  1. It’s not the critic that counts.
    If someone offers you constructive criticism, listen. But if they are just trying to stop you from creating something you’ve always wanted to create, ignore them.”It is not the critic who counts; not the man who points out how the strong man stumbles…. The credit belongs to the man who is actually in the arena… because there is no effort without error and shortcoming.” – Theodore Roosevelt
  2. Write down goals… track them… share them.
    It’s not good enough to just set goals. You have to write them down somewhere you will see them often. Then, evaluate your progress on a regular schedule. And even better, share them with other people and ask them to hold you accountable.
  3. You have to create good habits.
    Studies show that almost half of what you do every day is the result of habits. But since they are habits, you usually don’t even realize you are doing them. That’s why you have to actively pay attention to what you are doing throughout the day and then get rid of the bad habits.
  4. Turn off notifications.
    This is a big one that I only recently discovered. You should turn off all notifications on your phone (and elsewhere) unless you really need them. You don’t need constant beeps and buzzes for the little things. They will distract you from what really matters.
  5. Give First.
    Give your unconditional support to your community. Don’t ask for anything in return. Just help people. More often than not, at some point in the future, you’ll benefit. But even if you don’t, you can’t live a full life if your community isn’t doing well. (h/t TechStars)
  6. Find a mentor.
    It doesn’t matter how old you are, or how far you are into your career, there is almost always someone out there with more experience than you. Find them. Ask them for advice. But also respect their time and don’t overreach.
  7. Be a mentor.
    Mentoring people with less experience helps them… and you. It forces you to think about what they need to do to succeed, which you can then use to evaluate where you are in your development. It also helps you to break down complex issues into easier to understand terms.
    Bonus: Judge a competition
    . When you are placed in the judge’s seat, it helps you to better understand how judges will evaluate you when you are the competitor.
  8. Learn when to say yes and when to say no.
    If someone asks you to do something outside your comfort zone, say yes and figure out how to do it. That’s the best way to grow.At the same time, you have to learn to turn down a lot of things. There are an infinite number of things that can distract you. You can’t sit on every board. You can’t take every coffee meeting. You can’t go to every party. You can’t do everything.Remember that “your priorities are shown by where and on what you spend your time.”


  1. No one is special.
    Humans just like you and I built everything around you. They are not special. You are not special. I am not special. Everyone is capable of doing great things and everyone that achieves great things failed along the way. You will too.
  2. Don’t overfill your teacup.
    Your mind is like a teacup. It can only hold so much. This comes from an old parable: An overly-busy young man visited an elderly monk seeking advice for his anxiety and stress. The two sat down and the monk poured himself a cup of tea and then poured a cup for the young man. When it was full, he continued pouring as the tea poured over the sides of the cup. The young man shouted “Stop! Can’t you see the cup is full?” The monk paused and said “Your mind is like the cup. Unless you free up space in your mind, I cannot help you.”
  3. Some things are up to you, some things are not. Focus on the former.
    I’ve been introduced to Stoicism via a few books in the last year. One core concept is that the absolute best way to live a happy life is to focus your energy solely on the things you can control. To do this, don’t focus on what other people think. Rather, internalize everything.This is related to concepts in Zen Buddhism as well: “It is the way you look at things and the way you relate to them that determines your state of happiness or unhappiness, not the things themselves.” – Chris Prentiss
  4. There are two kinds of mindsets: Fixed and Growth.
    A fixed mindset is defined by believing that your qualities and talents are fixed at birth, while a growth mindset is defined by believing you’re your qualities and talents can be cultivated and improved over time. People with a fixed mindset are more likely to fear failure because failure would indicate that they, as a whole, are a failure. But people with a growth mindset are not afraid of failure because they know that failure is just part of the process to becoming great. It’s that growth mindset that drives many people to achieve success. And best of all, you can change your mindset. For more, read this book.
  5. Don’t ignore your physical health.
    It’s so easy to ignore your physical health. I did. But the moment I began working out and focusing on my physical health, I realized the benefits carried over into just about every aspect of my life. I have more energy, I have better focus, I have less anxiety, etc. Not only is that good for me, it’s good for my business.
  6. Don’t ignore your mental health.
    Your mind is a muscle. And just like other muscles, you need to protect it from injury and work it out to make it stronger.This takes different forms for different people. For me, I’ve found that studying philosophy (specifically Stoicism) and Zen Buddhism helps. I’ve learned how to reduce anxiety and stress by internalizing everything and focusing more attention on my thoughts and actions. I’ve also learned that overthinking is the biggest cause of unhappiness and that if you focus on unnecessary and speculative questions, you’ll just create imaginary problems. (This is related to lessons 9, 10, and 11, above.)

Working with other people 

  1. Trust your gut.
    If you’re exploring a potential business relationship with someone, and your gut says don’t do business with them, then listen to your gut. It’s probably right. In the last five years I can recall two very specific examples of this­–my gut said something was wrong with the other person, I ignored my gut and did business with them, and things fell apart. I later learned that others in the community had the same bad experiences with those people. Some people are just bad people…
  2. Always ask questions – Never assume you know the other party’s intent.
    If there is a disconnect between you and another person, it’s most likely due to a lack of understanding. In those situations, you should always ask for clarity. Often, it is the fastest way to get to the bottom of the disconnect and find a winning solution for everyone.
  3. How to hire independent contractors.
    Don’t hire independent contractors without a contract. The nature of the relationship is that both parties are independent of one another. Thus, a contract is critical.
  4. Don’t charge too little.
    Too many people charge too little. I get it; it’s hard to set a high rate and even harder to communicate it to prospects. But your rate is a reflection of your quality. Good work shouldn’t be (and isn’t) cheap. After you set your rate, be confident when you share it with others.
  5. Charge based on value, not your time.
    I love this story I heard years ago on NPR: A man opened a new restaurant and asked his friend if he could line up a review in a popular magazine. The friend said “sure, if you pay me $10,000.” The restaurant owner said “fine, whatever it costs.” The friend hung up, called the magazine editor, and lined up the review in just a few minutes. When he called the restaurant owner back to share the good news and request payment, the restaurant owner said, “I’m not paying you $10,000 for five minutes of work.” The friend then said, “no, you’re paying me $10,000 for my work over the last 20 years that allowed me to get you a review in less than five minutes.” The restaurant owner shut up and paid the bill.The moral of the story: Always charge based on the value you provide.
  6. Be transparent about pricing.
    When you work with clients, you can avoid a lot of disputes simply by being transparent about your pricing. All too often you do the work, invoice the client, and then they delay paying you or refuse to pay you. In most cases, that’s because they didn’t know the rate up front. (This is why I have pricing on my website and why I built my contract shop.)

Running a Business 

  1. Numbers are boring, but you gotta get them right!
    I like to say that your most important metrics are your financial metrics. That’s because you can’t succeed in business if you don’t get your financials in order. I met with an accountant before starting my company and I meet or talk with him regularly. You should too.
  2. How to manage your accounting records.
    As early as possible, create a good chart of accounts–a list of all the places you are likely to spend money and all the places from which you are likely to receive money. For me, I divide my firm income into various accounts (like freelancers v. startups) and I divide my firm expenses into different accounts (like subscription marketing v. non-subscription marketing). Doing this makes it easier to track your financials and understand where money comes from and where it goes.Also, you should absolutely invest in a cloud-based accounting tool. I really like Xero.com but I also hear good things about FreshBooks.com.
  3. How to find a good bank.
    Picking a bank that works the way you work is critical. If you care about digital tools, make sure they have great digital tools. If you care about in-person communications, make sure you like their bankers. Further, make sure your bank integrates with your accounting tools.
  4. How to run payroll.
    This one is simple. Use Gusto. I absolutely love Gusto for paying employees and contractors. For a low monthly fee, I can manage my payroll using their dashboard, they take care of all state and federal filings, and they even manage the tax withholdings, escrow, and remittance. It’s awesome. (ps, that’s my referral link)
  5. Don’t screw up your taxes.
    Most small businesses are “pass through” entities. This means you’ll report your income on your personal tax return and you’ll likely need to pay estimated payments to the government. As a result, you should set up a good system to track your income and set aside roughly 15-30% for taxes. The best way to deal with this is to meet with an accountant to help you get organized.
  6. Don’t use your email inbox as your task list.
    I did this for a long time until I realized it was a stupid way to manage my tasks. If you do this, you are giving everyone with your email address power over your task list. You need to create a plan for short term and long-term task management. I use Asana for long term task planning and a paper journal for day-to-day task lists.
  7. Don’t build too much too fast.
    Always test your assumptions. Ask prospects if they will buy your product/service. Then build a small version of it to see if they actually do buy it. Then expand. I learned this the hard way and spent way too much money and time building something I couldn’t sell. Don’t repeat my mistake. In short, don’t build too much, too fast. Get feedback first.
  8. Never do anything just because “it’s always been done that way.”
    You should always experiment with new ways of doing things. The fact that something has “always been done that way” is probably the worst justification ever to do anything. Within the legal industry, this is actually kind of easy because most lawyers simply copy old contracts and never innovate. I try to avoid that at all costs.
  9. Why coworking is awesome.
    I’ve been coworking for five years and I love it. I’m surrounded by creative people all the time and I’m constantly meeting new people. Since WeWork takes care of everything from cleaning to printing and WiFi, I don’t have to worry about those little things. I love it. PS – you should check out WeWork. (that’s my referral link)
  10. Why coworking sucks.
    Some people will hate coworking. If you don’t like being interrupted from time to time, and don’t like being around a lot of people, then it may not be for you. In most coworking settings, you can get a private office (which works really well for me) but some people will still think that is not private enough. Also, if you need a lot of privacy for sensitive meetings, coworking may not be for you.
  11. How to streamline things.
    If you start a business, you’ll wear a lot of hats. That’s why you have to streamline as much as possible. Using online forms, online billing, digital signatures, etc. can really help you. For example, when a new client engages Venture Legal, I use an online intake form to capture their information. I then use a DocuSign template to quickly get an engagement letter signed. I then do all of my invoicing through Xero and integrate with Stripe to allow for online payment. It takes some time to set all of that up, but it makes me more efficient day-to-day.
  12. Don’t use a free email provider.
    If your email says @gmail, @yahoo, @aol, or whatever, at the end, then I question how serious you are taking your business. Register a domain, then set up G Suite (Google) or Office 365 (Microsoft) or some other email provider so that you can have an email address with your domain in it. Further, that provides much greater privacy than using a free email platform.

Marketing & Getting Work

  1. Pick an easy business name.
    There is a lot of advice out there when it comes to picking a business name. You should think about trademark law and marketing in general, but one thing people don’t think about as much is the practical side of things. For example, is it easy to understand your name when you use it in a conversation, or what about when you give your email address to someone over the phone?
  2. Protect your trademark.
    As mentioned above, you need to think about trademark law. I’ve written a lot about that. You can learn all about trademark law in my free ebook, How to Protect Your Intellectual Property.
  3. How to create a brand.
    My favorite definition of “brand” is that your brand is “what other people say about you when you are not in the room.” While that is largely not up to you, you can take certain steps to influence what they might say. First, you have to provide amazing service to have a great brand. And second, you have to take marketing seriously (see the next lesson).
  4. How to market your services.
    With your branding in mind, come up with two or three key messaging points. These are the things you want people to remember about you after engaging with your marketing. Then, make sure that you use those in all of your marketing messages. In terms of where to market, this is easy–go where your customers are. That may be networking groups, large events, online in social media, whatever.
  5. How to be niche.
    If you are going to err, err on the side of too niche. Find a niche market and own it. Do everything you can to support that niche, make yourself the go to professional in that niche, and don’t worry about other niches. Sure, you can work in other niches from time to time, but your primary focus (and certainly your primary marketing focus) should be within your niche.

What lessons can you share?

It’s impossible to capture everything I learned in the last five years into just one blog post. But this is a good start.

What about you? What invaluable lessons have you learned about entrepreneurship or life in general? Shoot us an email or connect with us on social media to let us know!

(This article is general in nature and is not legal advice. Image: Adobe/thanksforbuying)

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