in entrepreneurship

Entrepreneurship: Year One

My first post in 2011. Good thing it’s an important one…

It’s been one year. One year since I started this maiden voyage of entrepreneurship. One year since I walked into my nine to five and walked out with two weeks severance and a “have a nice life”. Today marks the one year anniversary of leaving corporate America and giving things a go on my own.

Now on my second business, I’ve learned a lot and grown exponentially as a professional, and more importantly, as a person. There have been ups and downs, many times where I’ve wanted to say “screw this” and get back into a nine to five routine, but as other business owners and entrepreneurs can attest, their is something addicting about living live by your own terms and being the master of your own domain.

The word of the year for me, by far, was focus. Focus encompasses everything I’ve been through this year, and focus has helped guide every decision I’ve made. Focus is the one thing, above all else, that any aspiring entrepreneur must have to see “success”. It’s the one thing I’ve continued to find solace in as a professional and as an individual.

And truth be told, this has been a very successful year. I don’t like to toot my own horn or dust my shoulder off, but I’m big enough to embrace my own successes, just as I’ll be the first to admit when I’ve fallen short and, by public definition, failed.

Through it all, I’ve been very transparent online – I’ve allowed all of you who are interested into my life on a very personal level, and many of you reading this have watched me evolve over the past year. Without your support, this would have been a much, much more difficult road to travel, and since the very beginning of this still relatively new chapter in my life, the readers (that would be you) have been there to wish me the best.

So, in true “year in review” fashion, I have a couple of “life lessons” to pass along to those who may be traveling down a similar path or are thinking about turning over a new leaf in 2011.

Believe in yourself and trust your instincts

God, it sounds so cliche’ I almost hate myself for writing it, but it’s said over and over  for a reason – because it’s true. The one person you MUST learn to trust completely is yourself. Your instincts will not steer you in the wrong direction, and if they do, embrace the poor decision and learn from it. The worst feeling in the world is having to say “I knew I should have done that”. Don’t be that guy, go with your gut and stay true to yourself.

Focus on your client’s happiness

Your ideas and your vision will get you far, but at the end of the day, success falls on your client’s happiness. Do everything you can (within reason) to make them happy. As a designer, developer, and strategist it’s my goal to get clients thinking in new and innovative ways, guiding them toward “outside-the-box” reasoning – but there’s a fine line between enforcing your ideas and FORCING your ideas – don’t do the latter – guide your clients toward the light, but let them be the decision makers and do everything you can to reflect their vision (without losing yourself). A satisfied customer is the best customer.

Don’t underestimate (or overestimate) your value

Having traveled quite a bit in the past year, chatting with current and aspiring entrepreneurs, it’s unanimous that one of the most difficult tasks of an entrepreneur or freelancer is determining your own value? The age old question: “How much do I charge”? I can’t answer that one for you, but I am here to tell you that you’re probably worth more than you think, just maybe not THAT much.

Also, an extremely important note: Your pricing model will change, your rates will evolve as your own personal needs change and your skill-set evolves. Don’t be afraid to up your rates – know your worth and own it. There’s no “going rate” for what Proof does, you can pay peanuts or you can empty your bank account for marketing services – it’s not about competing, it’s about knowing your position in the market and embracing your worth.

Ironically, the best part of working from home is not working from home

Sounds weird, I know – you’d think being able to work from home would be the best part of being an entrepreneur, and don’t get me wrong, all the Saved by the Bell reruns and Law and Order marathons are great, but my productivity exponentially increases when I get off the couch and head into a coffee shop. It’s like Jedi-mind-tricking myself into thinking I have to wake up, shower, and head into the office. Changing up your scenery does wonders.

Total freedom is a fallacy

Hear me out. The one thing you’ll hear every entrepreneur talk about is freedom and how great it is to have freedom. And it is great – but total freedom is something we trick ourselves into thinking we want. Now that I’ve been doing this for a year, I find myself craving structure – not “work from a cubicle” structure but structure to my work-day so I don’t find myself constantly working all hours of the day and being on call 24/7. I now appreciate structured freedom and am working now more than ever on finding my own work-life balance. Like everything, it’s a work-in-progress.

Be up front about setting your own expectations

One of the lessons I learned very early on is that you can’t be everywhere all the time. You can’t do everything. You can’t please everyone 24/7. So stop trying. You will absolutely drive yourself nuts (been there) if you create the expectation that you’re always on call. Don’t create an environment for yourself in which your clients believe you’re always reachable. Why? As soon as you do, you create an unrealistic expectation. The minute you can’t reply to an email at 11pm, the minute you cant fix someone’s website at 3 in the morning, your clients are panicking wondering where the hell you are. Put simply, don’t do it to yourself – be up front about your expectations and relay those to the people you work with.

And for God’s sake, don’t let your work consume you

The best part of what I do is that I love doing it. I love my life and I’m humbled that I’m in the position to be writing this post at 25 years old – I never thought I’d be here, but I am here, so here I am. But, you enter treacherous territory when work is more than a part of your life, it is your life. Know where to draw the line. Know when to unplug and spend time with your family. Know when to call it a day, know when to say no to a new project that comes your way. Don’t bite off more than you can chew and don’t try to do it all.

So there you have it, a year in review, and what a year it’s been. I take everything I’ve learned in year one and will carry it with me as I continue down the path of year two. There’s a lot of great things ahead of me, a lot of challenges to overcome, and a lot of success to be had. I’m looking forward to every minute of it…

(Photo c/o Rob Williams)

Add Your Voice



  1. Matt,

    I find your story of the last year inspiring on so many levels. I know it’s not easy putting your life “out there” for everyone to see. But, from the day you were out of a job until today, you’ve shown that if you put your mind to something, anything is possible. Here’s to the future… and to success!


  2. Great post, Matt. It’s been about a year of entrepreneurship for me, too (left the corporate job 1-1-2010) and you are spot on with your life lessons. I’ve seen the ups & downs of all of these and come to the same conclusions. You couldn’t have said it better. Best of luck in your “second year!”

  3. Well done Matt. It’s an exciting journey eh? I enjoyed reading this – particularly your point about letting customers decide. And sometimes that requires a lot of patience and that can seem tough (to me at least).

    If I may, I would add learning from my mistakes to the list. I make a lot of ‘em – through trying new things. Mistakes are a great learning experience and as owners of our own business I think they are an enjoyable part of what sets us apart from big established corporate dinosaurs (the kind I used to work in anyway).

    Here’s to the next purposeful, enjoyable year.

    • It does require (a lot) of patience to accept that the customer needs to be right. Of course, the best customers are those who trust your opinion, but also challenge and offer their own – it’s all about give and take on both sides.

      Mistakes are going to happen, to be sure. Learn from them and they help you grow, don’t and, well, they’re just mistakes…

      Cheers my friend!

  4. Fantastic post Matt. I know my business is quite a bit different but this really does fit into any entrepreneurial role. These points are learned over and over and over again as the years go by.

  5. Thanks for your thoughts. I am just a month or so into working for myself and am already hooked. I can’t imagine going back to a traditional 9 to 5 anytime soon. I look forward to the next 12 months and the moment I can sit & reflect on my one year mark. I hope I can say I’ve been as successful as you have! I have trust in myself so I’m sure I will.

  6. Love this Matt. I wrote a similar one recently and I always find your loyal community respond most to when you put it out there for all to see (within reason) which it seems you do naturally well.

    Ironically my word for the year is FOCUS. It certainly helps when starting out as entrepreneur’s have a habit for getting distracted by those big bright shiny objects.

    I too change up my scenery a lot and am a constant cafe entrepreneur, as well as trains, planes and buses too or town squares in remote villages!
    And I agree you need to get up and out in the morning and create a semblance of structure in order to actually create more freedom.

    Congrats to you and looking forward to chatting on Skype this week coming – yep I’m sending an email!

    • Traveling (planes especially) is when I’m my most productive – with that being said, I really need to travel more often!

      Look forward to chatting soon, feel free to shoot me an email anytime and we can set something up!

  7. As I transition into college life next year (and hope to start a business along the way), this post’s wisdom will be invaluable.

    Even if I don’t end up running a business, the latitude I’ll have as a student will make my life a lot like an entrepreneur’s. I’ll have freedom, but it won’t be complete by any stretch, since I’ll have to devote a huge chunk of my time to doing work. And, of course, it’ll be extremely easy to get overwhelmed and take on too many projects – so I feel like my college life will be a pretty good analog to entrepreneurial life, though with slightly less freedom (living on campus, not making money, having to attend class).

    Still, the same rules -like the ones you’ve outlined here- seem to apply everywhere. Being a great manager of one (yourself) makes a huge impact in every sphere of life, not just running your own business.

    • They do apply to pretty much everything. That’s the beauty of it – what I’ve learned in the past year as an entrepreneur of course helped me grow professionally. But more importantly, it’s helped me grow as an individual. Cheers!

  8. So many great nuggets here that I figured I’d respond to them all :)

    1) Believe in yourself and trust your instincts
    – YES. We have to have faith that we know what is best for us. Our instincts, our logic, is swimming through our heads for a reason. Mind you, this is coming from you and I, people who have a clear understanding of what we enjoy doing and what our values are. This piece gets more confusing, unfortunately, with people who for whatever reason are half asleep and are unsure of what they care about. It takes some skilled filtering, and a deep understanding of ourselves, to take advice that works for us and ignoring well-meaning but poor advice.

    2) Don’t underestimate (or overestimate) your value
    – I’m not freelancing, but I’ve seen too many local artisans reluctant to sell their work, and then there are those I’ve seen who sell hand-made scarves for hundreds of dollars a piece – c’mon, BE REAL. Know the market, embrace the market.. and this takes research and work. Not enough artists do this, and you wonder why the term “starving artist” floats around. Very frustrating.

    3) …Not working from home
    – I agree. I mean, I’m a teacher who works in a school, but in the evenings and weekends when I’m preparing lessons/marking or even working on other projects, I find I’m more productive when I leave my home every once in a while. Coffeeshop, teahouse, library, whatever – change of scenery is so absolutely necessary to restimulate.

    4) Total Freedom = Fallacy
    – True story. I’ve come to realize too more than ever that time is ours to manage. We can leverage it however we want. My 9-5er friends, I find, often have more free time than I do because they make time after work and on weekends to do everything they love.. whereas I’m constantly working on SOMETHING after hours. Also, as a teacher, our work can consume us if we’re not careful. Setting a structure, looking at our week and allotting time for certain activities – organization and set work times can actually create greater freedom to do what we love.

    5) Setting your own expectations
    – Word. Learn to say no because we need to. We can’t do everything and still do all of it justice. People deserve better than to get half-assed attention from us.

    6) Don’t let the work consume you!
    – Working on it. I love my work too much, and I’m constantly thinking about how to do things better.. but at least I’m putting in the effort to spend time with my friends and family.

    p.s: Happy New Year, Matt! Here’s to another epic year :)

  9. Congratulations on your first year of business success! You’ve navigated so many changes personally & professionally this year and managed it all with grace. Thanks for sharing your evolution in business and in life with all of us here, and I hope year 2 is even more successful!

  10. Hi Matt:

    Congrats on one year!! These are some good tips as I consider doing more freelance and project work. I especially like your thoughts on freedom being a fallacy. I sense there are a lot of people out there who want to do more entrepreneurial work. I also sense that a lot of these people think it’s easy or that having a blog or website means automatic money. Once again, thanks for these thoughts as I embark on some adventures.

  11. Hi Matt:

    Congrats on one year!! These are some good tips as I consider doing more freelance and project work. I especially like your thoughts on freedom being a fallacy. I sense there are a lot of people out there who want to do more entrepreneurial work. I also sense that a lot of these people think it’s easy or that having a blog or website means automatic money. Once again, thanks for these thoughts as I embark on some adventures.

  12. Hi Matt! Good stuff! Didn’t realize the last post I commented on was from a year ago on your layoff! Love to learn more about whether you did an LLC, or an S-Corp and the difference, and all that good stuff about entrepreneurship. Would be great to connect one day. I’ll be reading your archives. Cheers, Sam

  13. Hi Matt,nu00a0nSo I find myself playing catch up through your life lessons and experiences. I can really appreciate your words being that I too am “young” (22) with the “settle-for-no-less” mindset. Thanks for giving back and fueling new spirits. nu00a0nRespectfully,nAllen T. Graham

  14. I’m a bit late here. But the point you made is pretty much timeless. It’s been 6 weeks since I quit a well paying job as a creative director to start my advertising studio. 6 weeks of realizing that the clients who thought I was a rock star are now hesistant to back a ‘new guy’. 6 weeks of forcing myself to get up in the morning and go to ‘office’ even if there may not be work. 6 weeks of thinking of all my friends who are switching jobs and getting fat pay checks. 6 weeks of calling up people for business. 6 weeks of….
    The thing is I know this is good for me in the long run. But its just so damned difficult in the present. And that’s the whole point of being an entrepreneur isn’t it?
    Great post Matt.Hope you have an even better second year.

  15. Awesome, awesome, awesome. So much wisdom in this post. I’ve always admired you, Matt and I’m glad to hear that things are still going well. Kudos!

    • Thanks so much, Sara. That means a lot. it’s the support of people like you that got me to where I am today, and keep me motivated each day. Thanks for being a part of the little ol’ community I’ve built here. Hope all is well!

  16. Matt,

    I am about to go out on my own, thank you for sharing your year in review.  I appreciate you putting your thoughts and lessons learned online for all of us to read.  Your story is an inspiration and I hope I am writing about my ups and downs as a successful entrepreneur next year at this time.  I am going to be structured, focused and in touch with the fact that I need to unplug from time to time and enjoy my family.  Make it a great day my friend, take care!

    ~Harrisburg, PA

    • Thanks, Chris. And best of luck as you go out on your own! It’s hard, stressful, and challenging, but ultimately, 100% worth it. If there’s anything I can do to help along the way, don’t hesitate to reach out. Cheers!

  17. Hi Matt

    I’m starting the same voyage – hope to be able to ditch the desk within a year! Tried it once before (nearly ten years ago) – left job sold house and moved country with my partner (now husband). It didn’t work out and we ended up back in UK with no job and no home. Now we’re back in the rat-race, with a mortgage and two kids. So it’s kind of scary ‘rocking the boat’ – but there are so many new opportunties out there these days. I’d love to ditch the job now but my aim is to get myself set-up first with enough semi-passive income coming in before I hand in my notice. You can follow my exploits through the year on my website:

    Thanks again for your blog – I’m glad I found it!

  18. Truly inspiring words. I learned about the expectations setting thing the hard way, and slowly fixing it now. There’s definitely times where you have to “make them wait” just for the sake of keeping their expectations at a level that can be met for a long, long time to come.

    Great post, and well done with all your success!

  19. This has been a worthwhile read. I am currently an academic that does a little freelancing on the side. Right now both jobs are suffering because I lack focus and I’m overwhelmed with tasks – what a shame. Meanwhile, I’ve been doing some introspection thanks to your article. Your first point about focus, and your last point about ones work consuming him/her resonated quite well with me.

    I am so going to bookmark this site. Thanks

  20. Interesting article Matt.
    Indeed, most entrepreneurs are not very good at maintaining an optimal work-life balance.
    They press on till ungodly hours in the illusion that they initially need to work long hours to get established.
    The truth is, not knowing ‘when to turn off’ can cause burnouts, thereby adversely affecting health, family and business.
    Clients don’t really want to trust their projects to someone who looks haggard and sleepy.