27 things I learned from 5 years in business

Chris Esh

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This April marked five years since I left my last “real job” at a nonprofit and dove full-time into starting a business. I had just spent about a year self-learning code and basic design in my free time. I felt far from ready but realized I’d never get things off the ground while working full-time at a day job and having a 2-year-old at home.

So I dove in headfirst, not really knowing what to expect.

While I had a competent skillset for website building, I realized immediately that I knew precious little about the actual mechanics of running a business. Like how to find clients, how to write a proposal, how to charge, how to manage finances, how to run a successful project, how to provide customer service, etc.

Business schools, business seminars, and books have their place I’m sure, but there’s no substitute for the actual experience of running a business. Through trial and error, feast and famine, and watching how lots of other business owners operate, I’ve learned a few things over the years.

Running a business is an accelerated learning program with a quick feedback loop. I had no bosses or coworkers to blame if things didn’t work out—the responsibility was solely mine. I got to decide who to work with and under what terms, then own the successes or frustrations that came from those projects.

If I didn’t like something it was up to me to change it. I could try new things, change my process, raise my rates, make videos, etc. without needing anybody’s permission. Which allowed me to experiment, fail/succeed, reflect, and try again until I found what worked.

Five years older and a little bit wiser, here are a few lessons I’ve learned along the way:

  1. Trustworthiness and good communication are more important than hard skills in any service industry. They are rare and thus highly valued. These “soft skills” are what kept me afloat over the years while I gradually gained experience and built my skillset.
  2. You have to get going to get good.  Don’t wait until you feel “ready.” If you’re anything like me, you’ll never feel ready.
  3. If you actually care about your clients and take pride in the quality of your work, you can often outperform your overpriced competitors who have no passion.
  4. Be patient. Five years in, the two most valuable assets my business has is experience and a strong referral network. But these take years to develop. The key in the early years is to survive long enough to start to reap the rewards of all these seeds you’ve planted in the early years. Don’t worry too much about metrics the first years. If you make enough to stay open for another year, well done.
  5. Keep costs down, both in your business and personal life. When you can live comfortably on $4k a month in after tax income, it’s far easier to stay afloat than if you need $8k a month.
  6. But do spend money on:
    1. Education. I spend $1k on an online course for WordPress business owners which felt like an insane amount of money at the time. But it proved to be one of my best investments ever, and likely what guided me into a profitable business. Also I also have a rule of unlimited spending on books and other learning resources.
    2. Hiring people to do things you aren’t good at. My first year in business, I did my own taxes because I didn’t want to spend $400 for an accountant. It took tons of hours and made me super nervous I did something wrong that would get me audited. The next year I paid an accountant and he helped me change up my business structure and saved me $3-4k the first year.
  7. Take responsibility for everything that happens and learn from it. I’ve had a few really crappy clients over the years, and I’ve learned (mostly) not to blame them when things go sour. Instead I ask “Who hired them?” and the answer is obviously me. Then I ask what red flags I missed that I can look for next time to lessen the chance that this happens again.
  8. Recurring revenue is gold. I started offering monthly website care plans towards the end of my first year. Growth was slow but steady, as I added a handful of clients a year and few ever leave. Now I’m up to almost 40 clients and a dependable chunk of monthly revenue, which gives me much more freedom to pick and choose web design projects.
  9. Post on social media enough to remind people you exist and why they like you—otherwise people will forget you exist. But don’t try to sell on social platforms. My two favorite types of content are: 1) Providing helpful advice, ideas and resources to my target audience and 2) Showing my work, whether sending a client shoutout for a newly launched website or showing steps in the process as “the sausage is being made.”
  10. Protect your nights and weekends relentlessly. Your work will expand to fill the available space so if you get in a habit of working off hours, it becomes extremely difficult to switch back.
  11. Businesses (and careers) are built on relationships. Always be open to connecting with professionals relevant to your industry. Unless they’re trying to sell you something disguised as a “mutually beneficial partnership,” in which case ignore them.
  12. Have an abundance mindset. Make friends with your “competitors”—there’s enough room for more than one fish in this pond.
  13. Trust your gut when interacting with clients, potential partners, etc. Every once in a while I get an uneasy feeling about someone, that I don’t quite trust them and their intentions. I’ve ignored this hunch enough times to discover that it’s rarely wrong.
  14. Business cards get thrown away and forgotten. Get in the habit of connecting with people on LinkedIn whenever you make contact. This will keep you connected long beyond when they’d otherwise forget about you.
  15. High-quality clients make my work enjoyable and engaging. Bad clients make me hate my work. The sooner you can figure out how to distinguish the good from the bad (and then figure out how to attract the good and repel the bad) the more enjoyable your life will be. 
  16. Be aware of insecurities and don’t take criticism of your work too personally. Revisions are part of the process, not an attack on your skills.
  17. Instead of trying to perfect a project before anyone sees it, try to get feedback at multiple points throughout the process, long before all the pieces are in place. This allows for course correction if there’s divergence between you and your clients’ vision, which is easy to do early in the project. If you don’t discover this until the end it’s a huge waste of time.
  18. Strive to be a true professional in everything you do. Whether clients love your work or complain, be friendly and respectful.
  19. But don’t be a stuffy professional. Be human, tell jokes, treat your clients like friends. Let your unique personality show through.
  20. If you mess up, be honest about it. It sucks when you make a mistake, but trying to hide it makes a bad situation worse. If you instead take responsibility, fix it to the best of your ability, and apologize for the error, most reasonable people will be grateful and understanding. I have multiple clients that actually seemed to like/trust me more after I made a mistake, explained what went wrong, and promptly fixed it.
  21. Always be learning and always keep an eye out for new/better ways of doing things. Don’t get in the trap of doing things a certain way because “this is how we’ve always done it.” That’s the fastest path to irrelevance. In the last 5 years, I’ve significantly revamped my website building tools/process 3 times as new, better tools have been created. I expect this to be a constant, ongoing process.
  22. Be ruthlessly disciplined about how you manage your email. You’ll get nothing done if you spend all day in and out of your email. Instead: 1) Remove all email notifications 2) Schedule when you check your email 2-5 times per day 3) When you check your email, process all new messages and add any tasks to a to-do list—don’t use your unread messages as your to-do list.
  23. Schedule uninterrupted blocks of 2-4 hours for deep work. Nothing meaningful gets done in 30-minute chunks. The best way to make this possible is to cluster your meetings during a couple specific days of the week so the other days are meeting-free.
  24. Build a flexible network of freelancers and contractors that you can collaborate with as needed. I used to try to do everything myself but soon discovered that there are a lot of areas of my work that are either 1) Fairly simple and repeatable and thus don’t justify my hourly rate or 2) Requiring skills I don’t have that others can easily do. For these things I hire others.
  25. Build repeatable processes for everything. I’ve gradually been building checklists and process documents for all the things I do in my business. This saves a ton of time and provides a clear path forward when starting a large, potentially daunting project.
  26. Being a business owner takes faith and patience. I’ll go months without signing on a new project, then in a matter of weeks bring in enough new work to cover me for six months. While it’s tempting to lower your standards when things are quieter, don’t! I’ve had to sometimes turn down amazing projects because my schedule was too full with subpar commitments.
  27. Aim for the lifestyle you want, rather than making a certain amount of money. Define your “good life” and keep it on your radar as you make business decisions. Don’t grow your business for the sake of growth. I’ve talked to multiple successful agency owners who told me candidly they were making more money and doing more of what they enjoyed before they hired a team.

Onward to the next 5 years!


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