10 Lessons Learned in 10 Years of Self Employment

by | Mar 23, 2019 | Josh's Blog | 8 comments

10 years ago (March of 2009), I got laid off from my job as a cabinet maker. I began working jobs on the side to cover bills and soon after, started into the wild world of graphic and web design. Thus began my journey into self employment which I have not looked back from or regretted at any point.

Now, as I’m fortunate to run a 6-figure web design business and a growing personal endeavor here at joshhall.co to help other web designers achieve the same, I’ve decided to reflect back and put together my top 10 Lessons Learned in 10 Years of Self Employment.

I hope these will be helpful to you if you’re thinking about starting your own business, maybe you have a side hustle you’re wanting to grow or if you’re at the start of your own business journey already!

1) Embrace the 3 “P”s

  1. Patience – because as we’ll talk about next, good things don’t happen overnight and take time. You’ll also have to learn patience in every area of life when building a successful business. Patience with different personality types, patience with colleagues, patience with technical problems, even patient in your success.
  2. Perseverance – because running a business and being self employed is one, if not the hardest thing you’ll ever do. And you’ll have to persevere in areas you never thought of. Perseverance through the highs and lows of your business. Perseverance through the unknowns like “will I have enough clients this month?” “Will I be able to pay my mortgage, etc?” Even perseverance through the mundane of day to day emails, business life, etc.
  3. Persistence – because you have to be the one driving your business every day. You’ll have to be the one to steer the ship, cast a continuous vision and push through every challenge and failure that you’ll endure along the way.

2) Prepare for Delayed Gratification

In world where we’re accustomed to getting things instantly, you’ll need to have a new mindset when it comes to having any sort of business or financial success. Things don’t come easy, they don’t come quick and they don’t happen instantly.

The best things in business and in life don’t come easy and they don’t happen overnight. Instant success and instant returns, in my experience, are virtually nonexistent in the business world. You might spend days, weeks, months or even years for something to pay off but when it does…wow it’s sweet. And you’ll find the personal and professional growth that it took for you to persevere through the tough times is immeasurably valuable.

The worst thing I hear fellow web designers who are starting their business say is “I need to grow this fast,” or “I need this to get huge quick.” Of the many problems with those statements, there’s an underlying aspect of growth, sustainability and systems to be able to handle success.

You have to enjoy the process. Enjoy progress in the daily mundane details of small wins and remember what you’re building towards every day.

Success is a vague term that means something different to everyone. And while financial growth and stability is no doubt a big part of the term, it’s not all of it. I.e. – if you’re well off because of your business but are so stressed and overworked that you have no time to spend with your family, no time for a life outside of your email and tasks…I wouldn’t be quick to call that fully a success.

3) Don’t be Afraid of “Coopetition”

In the world of web design at least, there are freelancers and agencies who feel they need to be the sworn enemies of their competition. I’m sure the same is true across all industries. But what I’ve found is that when you embrace cooperation and even partnerships with your competition, it can lead to more referrals and more fruitful relationships all around.

I have several colleagues and competing web agencies that I often refer clients and potential leads to. And by doing that, they now return the favor. If it’s something that I “could take on” but know there’s someone who’s a better fit – I’m going to refer than and plant the seed to a much better result for all involved.

You’ll also be surprised at how much you’ll learn when you partner or work with your competition and help build each other up.

4) Prioritize your Systems, Processes & Automation

If there’s anything I regret in my decade of self employment, it’s the amount of wasted time I’ve spent in repeating the same thing over and over and over and over again or making life more difficult for my future self (or now my team) by not keeping things organized and investing in a system or process to make life easier.

Practically, one way I employ this is if I find myself repeating an email to a customer or team member, I either make it an email template that I can just open up and send or make a tutorial video or walk-thru saving me from repeating the same information over and over. It may take an extra 20 or 30 minutes initially to record and publish a walk-thru video but it’ll save countless hours in the long run.
I do the same thing for clients when we onboard clients to Basecamp, my project management platform. I used to have to explain over and over how to use the system and hope they got familiar with it quickly but now I just send a quick walk-thru video BY ME which makes it feel personal and saves me boat loads of time in the long run.

I could talk all day about systems and processes but we’ll leave it at that 🙂

5) Keep your Pace Calm & Sustainable

I’ve found that a lot of entrepreneurs, new business owners and start ups are super gung-ho, energized, pumped and work tirelessly and while there are times for those type of personality traits, I find that most of those folks wear down, fizzle out and ultimately call it quits frequently after about a 3-6 month period.

This is largely because their daily pace is not sustainable or mentally, physically and emotionally healthy. Even if you’re the type of person who can sustain a “crazy busy” style for a long time, it’s likely that your team and your family can’t. I’ve seen this time and time again with clients and colleagues who are so go go and they have an insane amount of turnover with staff because it’s just not a pace that can be sustained for the long term.

When anyone says something to the effect of “I want to be the biggest in my area or niche within a year and just crush it”… my eyes roll because I know even if they have some quick success, it won’t last long.

I continually battle going through seasons where things are so busy and I say “once we get these projects done or once I get through this string of tasks, then I’ll slow down or take time to workout, prioritize my well being,” etc. But then once that season passes, a new string of projects come online and it all continues. I’ve learned to be intentional about the daily routines to keep things calm and sustainable. Whether it’s making time for a walk or a workout no matter what, or stopping at a certain time to spend with family, or not checking email right when waking up, etc.

Now there are of course times where things happen and you’ll be busier than others but I encourage you to always ask yourself this…what would happen if I just wait to respond to this in normal work hours? Is this life and death or do I really need to worry about this right now? Probably not in most cases.

A couple good books that expand more on the subject are mentioned in the links below.

6) Invest in YOU

This is perhaps the most important investment you’ll make in self employment. It’s more important than the equipment you buy, more important than the space you rent or the business expenses you invest in. It’s the one investment that pays off in every area and keeps giving back year after year.

The self improvement and motivation space is often eye rolled and scoffed at but the fact is, if you don’t invest in yourself more than any other area, it’s likely that your business will fail. I can be the most talented web designer in the world, but if I can’t sell, I can’t communicate and I can’t work well with others…unless I’m working for an agency, my business is doomed.

Practically, for me at least, a decade of investing in myself has looked like:

  • Buying and reading a lot of business and personal growth books
  • Going to seminars and workshops
  • Joining networking groups and similar groups like toastmasters to work on communication and leadership
  • Investing in coaching services
  • Asking to be mentored and learning from others

It’s important to leave a certain amount of time per week open for personal investment no matter what business you’re in and no matter how busy you are.

7) Don’t Burn your Bridges

I’ve found that in business, it’s very easy to burn bridges, figuratively of course. Whether that’s shunning a potential lead who decided to go with a competitor or be quick to anger with something goes awry with a colleague or associate, or even to respond too negatively to a comment online…there are daily opportunities to burn a bridge that otherwise may lead to an opportunity or at least, a positive impact.

I’ll mention 2 prime examples:

  1. A now client of mine years ago got a quote from me for a website design. She said it was too expensive and decided to go a cheaper route. My first reaction was a little angry that I had spent a lot of time planning out the project, learning about her business and preparing a very in depth quote. But instead of being short with her, I let her know that the offer is always open if she has a bad experience and decides to come back.

    A month later, I received an apologetic voicemail saying she went the cheaper route, got burned and asked if the offer still stood and that she’s willing to do whatever it takes to work with me. She is now one of my best clients to date and never questions what I charge when we work together. Had I responded badly from the start, I would’ve burned that bridge and closed off what is now a great and profitable relationship.

  2. A comment on one of my YouTube videos came across very wrong and rubbed me the wrong way. While I’m not always a saint when it comes to responding (or preferably not responding to those type of comments) I slept on it and came back with a much more level headed response the following day.

    Little did I know that the persons didn’t speak English as a primary language and just worded things a little wrong. They came back completely different the second time and is now a student in one of my courses. I could’ve responded terribly causing them to go elsewhere and potentially ruining what is now a great chance for me to mentor them in web design.

So the long and short of it is – don’t burn your bridges. You never know where something may lead if you take the high road and leave an opportunity open for both sides. Now there are some people not worth working with or evening opening up an email from so don’t get me wrong 🙂 But more often than not, I’ve learned that what can be easily dismissed may lead to something better down the road.

8) Limit your Distractions

We live in a very distracted time and world. Between email, social media, texting, YouTube, podcasts and an endless stream of distraction based media, I could spend all day getting no deep or meaningful work done. And for me personally, this doesn’t even include responding to comments on my site or YouTube, or messages or comments in my Facebook groups.

Even as I write this, I know that emails and messages are coming in, I’m probably being pinged on Facebook and I have small tasks that are building – but in order for me to get the most important work done that I need to get done, I have to limit those distractions and focus my attention to the most important areas of my work.

Practically, for me this often means turning off my phone, closing my email, resisting the urge to check Facebook and to stop all notifications from comments and pings. I only get to those small level tasks when I WANT TO instead of being pulled every which way at any point throughout the day.

One thing that has helped me, especially as a web designer, is to have a blocked out section of the day for reactionary work. So I can focus on my deep level and most important projects at certain points and know I’ll get to that widget that broke on a website shortly, etc.

Whatever you do to limit your distractions and get to your most important work while you’re mind is fresh and not distracted…do it!! It’ll save your sanity and make you a lot more money down the road.

9) Don’t be afraid to Fail.

Seriously, it’s good for you.

You’ve probably heard this from every self help or business book and have seen it on inspirational quotes and memes all across social media but don’t be so quick to overlook it. It’s something that is so profoundly important and is wired in the DNA of every successful business owner sooner than later. The fact is you will fail and you will fail often. I’m not talking about the business failing as a whole, though in worst case scenarios, that might happen. But I’m talking about the little failures, sometimes daily failures that happen along the way.

Practically, this includes offering a new service that fails. A new product that fails. Going for that big client that you don’t land. Stepping outside your comfort zone and falling flat on your face in a presentation. Trying to add a new team member that didn’t work out. Opening yourself up to criticism and public opinion.

There are numerous little daily, weekly or monthly failures that will come and you have to be ready for and prepared to bounce back from without hesitation. Every business owner who has been in their game for longer than a few months will tell you that it’s key and that they’ve undoubtedly failed more times than they have succeeded.

The reality is that most people don’t take the leap because they’re afraid of failure. They’re afraid of what might happen if it doesn’t work out. What might happen if work gets too thin. What might happen if they can’t take on the stresses. What might, what might, what might…listen – probably all of that will happen. But it’s how you respond and get back up from a failure or setback.

And don’t confuse failing with quitting. They are vastly different. Going for a new product launch and ultimately failing at it will provide you with so many lessons learned and value teachings that you can learn from and apply to the next opportunity to make it successful. Quitting halfway through because you don’t know if you have what it takes to finish or you’re afraid of what might happen if it goes awry is a different ball game. There’s no growth. There’s only “what if’s” and personal disappointment in yourself.

This is particularly important if you’re a personality type that doesn’t respond well to failure and needed to get a perfect A on every test in high school. Traditional academia teaches failure is bad whereas the business world will reward it in a multitude of ways.

Practically, I’ve never seen this play out more than when I started my business and went to a networking event. An account who was clearly there because he was told to be and was a bored, somber presence about him, asked what I did. I said “I just started my own web design, business.” He said “wow that’s risky man, what if it doesn’t work out?” To be honest I think it took me off guard and I don’t remember what I said…but today I’d say…”what if it does?”

Moral of the story is, don’t be afraid to fail. Go for it. What’s the worst that can happen? Will you be living on the street if you go for your dream? I highly doubt that would be the case for most people who are starting a business. Yeah, maybe you will miss a mortgage payment one month. Maybe this venture won’t work out and you’ll have to swallow some pride and move in with the parents. But I’ll tell you what – it’s better to live life to the fullest and go for it rather than be a bored, shell of a person living in the fear of failure and wondering “what if…”

10) Be Nice

Those guys & gals don’t finish last after all…

Maybe nice guys finished last a few decades ago and maybe in certain industries, you need to be harder and meaner than others but I’d argue that in most industries and as proven in my field of web design…being a “nice guy” has paid off for me ten fold.

Practically this is shown in point #7 above when it comes to not burning bridges but it also plays out in every aspect of business. From how you come across on your website, how you are in person at a networking meeting, how you respond in emails and messages, how you handle conflict and tough situations with clients and internally with a team, to how you deal with people who aren’t so nice…

Nobody wants to work with a douche. That’s true from a team perspective and from a client perspective. I’ve also had this play out practically time and time again with colleagues particularly in the design field. Yeah I could totally send my client to this developer or designer…but they’re just not a very nice person and I know it’s not going to go well. So guess what, they just lost out on a job.

Being super talented but having a terrible personality will only fly for so long. I don’t know how many projects I landed through the years where they chose to go with me, not because I was the best or most talented designer, but because they liked and trusted me and knew it would be a good experience while working with me.

It’s amazing how far being a nice and cool dude or gal will get you. And in the digital age of anonymous commenting, loud opinions and non face to face confrontation, it’s easier than ever to not be nice. But if you’re nice in those areas particularly, it’s amazing what seed that plants 🙂

Well I hope you enjoyed the top 10 lessons that have made a huge impact for me in being self employed for a decade! If you have any you’d like to share if you have any thoughts on what I’ve shared, let me know in the comments below!

Links mentioned in the video:

Books mentioned in the video: