7 things I learned in my 1st year of chasing a dream full time.


This week marks one year since Jenny and I launched the biggest career adventure we’ve ever gone on. After 15 years at big companies we decided to strike out on our own. (I say “we” because it was definitely a team adventure with both of us looking out over the same railing of the same boat over the same ocean horizon. Hannah Crosby captured that feeling perfectly in her painting above.)

In reflecting on that, I realized I’ve learned a few things these last 12 months. Here they are:

1. Never blame a boss for holding you back.
For a decade I told myself “Oh the things I could do if I didn’t have a boss!” Last year I became self employed and found myself technically without a boss. Suddenly this overwhelming sense of panic set in that said, “OK, there’s no one to blame except you. You’ve talked a big game all this time, let’s see what you’ve got!” Never blame your boss or job from preventing you from doing cool stuff. Just do cool stuff now. Be honest that most of the time the person holding you back is you. (I’m the greatest hindrance to my own adventures!)

2. You will feel like the only one who doesn’t have everything figured out.
This is a huge myth. There’s a name for people who tell you they have it all figured out, they’re called “Liars.” I don’t have it all figured out. The older I get the more I realize life is like jazz, not classical music. You don’t get perfect sheet music to follow step by step, you get skills that you improvise as everything constantly changes around you.

3. You need people.
Out of pride and fear, I sometimes hide. I hole up, afraid that asking for help indicates that I’m weak or dumb. Shouldn’t I have things figured out by now? Won’t people doubt all my ideas if I tell them I’m scared and need help with a project? If I was talented enough, smart enough and awesome enough wouldn’t I not need people? These are the fears I hear sometimes. The truth is, I can’t do this alone. Andy Traub and Shauna Callaghan for instance helped me get my blogs back up. They were and continue to be amazing. Working on your own is a lonely, isolating business if you’re not careful. I’m learning to ask people for help.

4. Some people won’t understand.
I feel like a confused loser when people at dinner parties ask me what I do. I love saying “I write books!” but their faces often say, “That’s not a real job or that’s not enough of a job.” I feel like I have to justify my existence in those moments and usually just ramble until I have finally worn them down through an onslaught of words and sweatiness.

5. It’s fun!
The highs are high and the lows are low and the middles are sometimes confusing, but it’s fun! Every day is different and the joy you get to experience is worth the fear you have to face. I’m getting to publish a book with Penguin! I get to go on tour with Orange! I get to do a weekly mastermind with a group of guys I love. Our family did a crazy four week summer vacation/work trip. All of those things are a by product of daring to go on a adventure.

6. It’s easier to write books telling other people to chase dreams than it is to actually chase one of your own.

7. You can become a workaholic in approximately 4 seconds.
Your day never ends if you’re not careful. You’ll check the weather on your iPhone at the dinner table and the next thing you know you’re completely ignoring your family as you catch up on emails.

It’s been a crazy scary awesome year, which I think was also the title of a TLC album. I guess what I’m trying to say is if you’ve got a dream, you should try. I don’t mean quit your job, I don’t mean start a business. I mean anything. Try. Just try. I did this year and it was like everything and nothing I expected. Also, don’t go chasing waterfalls.

What is one thing you’ve learned about your job or your dream in the last year?

  • Joey E
    Posted at 04:49h, 18 September Reply

    I’ve learned that ambiguity is common in my new job / role. I hate not knowing exactly what I need to do. But then again, I have a great boss who is giving me the freedom to explore, dream, succeed, and fail.

    • Jon Acuff
      Posted at 07:04h, 18 September Reply

      You hit the nail on the head. I hate not knowing exactly what I need to do too!

    • J.T. Smith
      Posted at 10:28h, 18 September Reply

      I’m the opposite personality type. I love not knowing my next step and just going with the flow. To me, it brings out my most creative side and gives me room to brainstorm.

    • Philip
      Posted at 10:43h, 18 September Reply

      Joey E, that is absolutely on point, not “knowing” the perfect next step. I’m constantly telling myself to just take action.

    • Huong
      Posted at 11:04h, 18 September Reply

      I second this too! I HATE not knowing what to do, but like Marie Forleo taught me, “Everything is figureoutable.” and I cling onto that for dear life!

  • Andrew C
    Posted at 06:09h, 18 September Reply

    I’ve learned to keep my dream of location independence at the forefront of what I’m doing. This is a lot like a farmer who takes seeds that could be feeding his family now and plants them, but he’s looking forward to his harvest when he’ll have many times what he planted. Building my business over the last year has been a lot like that. Thanks for keeping me on track, Jon!

  • Chris Lawson
    Posted at 06:17h, 18 September Reply

    I’ve learned you have to be flexible and go back to the drawing board every now and then.

  • David Mike
    Posted at 06:40h, 18 September Reply

    Thank you for always being willing to share real information about your journey. The hills and the valleys, real is better than perfect. I’ve learned that there are people out there that will help you and ride along with you too see your dream happen.

  • Mike Dwyer
    Posted at 06:47h, 18 September Reply

    I’ve learned that our job is what we make it. Giving our whole hearts to our work leads to rewards, no matter what your career looks like.

  • Eric
    Posted at 07:06h, 18 September Reply

    Thank you for being transparent about being afraid and not always having the answers. You always show both sides of the coin. Again, thank you.

  • Jen
    Posted at 07:17h, 18 September Reply

    I’ve learned not to expect instant results, and to allow myself time and breathing space to build my dream. It doesn’t happen overnight. I’m also trying to learn to not be too hard on myself!

  • Will
    Posted at 07:36h, 18 September Reply


    I feel that even though I am writing a book for others to read and be encouraged by, it is actually a long letter written to myself challenging me to chase a dream. I have become the target audience. It’s scary.

  • Daniel Tomlinson
    Posted at 08:06h, 18 September Reply

    I would just like to ditto all of the above. Ditto. I tell my Team Members and future Team Members that residential cleaning is not rocket science. Starting and running a business is rocket science. It’s hard. If it wasn’t everybody would be doing it. Looking forward to the new book good man.

  • james
    Posted at 08:39h, 18 September Reply

    Great post, Jon! And thank you for sharing your journey with us. You encouraged me to start writing myself and just last month I launched my blog. Couldn’t and wouldn’t have done it without you inspiring me through your posts. Thank you!

  • Nikki Lerner
    Posted at 08:55h, 18 September Reply

    That the fulfillment of dreams are not just for “other people” (whoever they are), but for me too and that it is amazing what I can accomplish when I put some focus and intention to it.

  • Cheryl Barker
    Posted at 09:51h, 18 September Reply

    I’ve learned I have to persevere — again. Just when the dream was about to come to fruition, it slipped away. So once again, I’m pressing on and persevering. And I’m so very thankful I can trust it all to God.

  • Anna
    Posted at 10:25h, 18 September Reply

    Excellent, Jon; honest and inspiring. So appreciated, especially as I prepare to dive into TPQ full-time #soon 🙂 And congratulations to you and Jenny on a heck of a first year!

  • Stacy Zeiger
    Posted at 10:27h, 18 September Reply

    I’ve learned you can’t get comfortable. I freelance as a curriculum designer/writer and have a lot of clients, but I’m always looking for new opportunities and developing my own resources because the minute I get comfortable with the clients I have or the level I’m at, a client runs out of money or falls off the face of the Earth. By not being comfortable, I don’t have to stress when that happens because I’ve prepared for the possibility.

  • Lauren J
    Posted at 10:30h, 18 September Reply

    I’m learning – just started moving forward on this dream – that you have to be your own source of positive thinking. In my particular field of dreams (#moviepun), people are constantly telling you, “You’re not good enough. You’re not who we want. You need to be this or that.” It’s repetitive rejection that you can’t take personally or you’ll wallow in insecurity. You have to continually find your confidence and work really hard not to lose your identity or self-worth.

  • J.T. Smith
    Posted at 10:31h, 18 September Reply

    I learned the importance of diversifying your income streams. As a person who makes money from volatile industries such as affiliate programs, seo dependent websites, and social media, if any of those things take a hit it’s important that the other income streams are strong enough to support you.

    It is somewhat important to have multiple projects going at once, at least in my dream job it is.

  • Emily
    Posted at 10:37h, 18 September Reply

    I’ve learned that no one has to be kind, or even courteous to me. And I’ve also learned that I don’t NEED anyone to be kind or courteous to me. I can be secure in what God thinks about me and my work. Hard lesson for a sensitive introvert to learn.

    And as a missionary/ministry worker, I completely get the “that’s not a real job,” stare. And the enusing panic that causes word-vomit.

  • Joe Cox
    Posted at 10:38h, 18 September Reply

    I’ve learned that every day I’m looking back or worrying about what my dream will look like in the future is another day I’m not actually living it. I’ve also always known that dreaming about it is never enough. This year more than ever, I’ve learned that we have to make the conscious decision to step into our dreams, to do the things you know will point you in the direction of those dreams even though fear is knocking and you don’t feel qualified. Was it Lao Tzu who said, “The journey of a thousand miles begins with a single step. I’ve learned that I must take a single step. Today. Everyday.

    Thanks for the work you do, Jon. May you continue to be blessed indeed and may your coast continue to enlarge so that others may be encouraged by your work.


  • Aaron
    Posted at 10:48h, 18 September Reply

    I’ve been chasing my dream of monetizing my musical skills(composition, playing live etc.). The one thing I’ve learned I how much branding is involved in music, and that offering a unique product is a) really inspiring and b) remarkably difficult in terms of grabbing an audience’s attention over in the space of a year.

  • Courtney Jeffries
    Posted at 10:51h, 18 September Reply

    but what if chasing waterfalls IS my dream?

  • Belle Cagas
    Posted at 11:07h, 18 September Reply

    “The older I get the more I realize life is like jazz, not classical music. You don’t get perfect sheet music to follow step by step, you get skills that you improvise as everything constantly changes around you.” — As a musician, I totally get this. Even classical composers didn’t all probably quite get it in my opinion – their final score just had to be the ‘official’ one. But I bet Beethoven and especially Mozart would have played their music differently each time ! 😉

    Thanks Jon for leading our D&B pack tirelessly. Congratulations! You are doing a great job!

  • Vincent Pugliese
    Posted at 11:11h, 18 September Reply

    I love that #6 is so concise! I love the honesty. Wish I could join you for the meetup in Columbus, but I’ll be hustling that day. Can’t wait for a Pittsburgh meet-up!

  • Josh Canady
    Posted at 11:11h, 18 September Reply

    I have learned 2 big things. A lot of success is simply doing and completing. Its movement. Even if its not perfect just completing something gets you ahead of the game and can open up doors to the next thing. Most don’t even get to the doing phase and for good reason….it’s hard.

    Also, I was shocked by the amount of support (or lack there of) from friends and family. I had this vision that everyone around me would hoist me up on their shoulders and carry me into town square shouting “For he’s a jolly good fellow” when they heard I was chasing a dream or when I released something I had worked so hard on. The opposite was true and that was a hard pill to swallow. I am learning that you simply have to search for those who WANT to be in your tribe and believe in what they are doing. And that’s not everyone including many family/friends.

    Thanks for this post Jon!

  • Ketra
    Posted at 11:23h, 18 September Reply

    I love this post! I am learning how to let go of perfectionism and enjoy the little things in life. This is a crazy wonderful life meant to be lived out and appreciated. Thanks for always being so inspiring!

  • Tammy Helfrichs
    Posted at 11:28h, 18 September Reply

    You will doubt yourself and your decision, and not be prepared for how emotional the adjustments are. Having good people around you to process these feelings is crucial! Looking forward to what year 2 has in store for the Acuffs!

  • Steve Beal
    Posted at 11:35h, 18 September Reply

    Wow I just sat down to lunch and really needed to read this. Every single point you made has hit home big time with me in the past month. I read Quitter and Start and went to Kent Julian’s speaking boot camp because of those books 6 months before being downsized from my executive position of 28 years in May. So I took that as a sign to give it a go on my own and set a time frame of 2 years. My loyalty kept me there, but I am so much happier being gone. My wife says she has a new husband and my biggest struggle is patience and that is the one thing that God is teaching me.. The busy days are great, but the days I don’t have anything specifically to do are torture. It’s funny but I was just thinking yesterday that you were someone who did have it figured out. Thank you for your transparency.

  • Corie Clark
    Posted at 12:45h, 18 September Reply

    So much truth and wisdom in this post, Jon. Although I am not the primary income in our home, I still take my work very seriously. It’s so hard sometimes to balance it all and make sure I’m giving the most important things, like my family, priority.
    Thank you for this insight. My husband is starting a business and I’m going to pass this along to him. 🙂

  • Suzewannabe
    Posted at 13:31h, 18 September Reply

    “Ser up the contradiction and live in it.”
    I imagine that I am loved and wanted at work and am very smart and capable. Writing my accomplishments on paper and texting them to a friend made them real again. Like I was a freshly graduated person and the world was my oyster.
    This morning I wrote an abstract to AAPG.org with me as lead author.

  • Jim Woods
    Posted at 13:49h, 18 September Reply

    I’m only one month in, but I TOTALLY agree with every word of this. Could not agree more. Thanks for sharing this!

  • Lynne Childress
    Posted at 14:39h, 18 September Reply

    I have learned that my dreams are doable. I have to DO them. Great post.

  • Samuel J Hunt
    Posted at 16:42h, 18 September Reply

    I’m only doing a small, small part of my dream, and it is more scary and difficult than I ever imagined. However, I am learning to remind myself that (a) I am not alone and (b) I am actually using my talents and doing something I’ve always wanted to do, instead of not using my talents somewhere I don’t want to be.

    It’s hard not to just be awesome now and have to work and learn and grow into it, but there is purpose in it.

  • LW Warfel
    Posted at 16:52h, 18 September Reply

    I’ve learned that other dreamers want to dream with me. They understand me best and don’t see me as crazy. They want to see me live out my dreams, and they stay beside me to help and encourage me. I’m thankful to be part of Dreamers & Builders. and thanks, Jon, for leading the way!

  • Mike B
    Posted at 17:27h, 18 September Reply

    I’ve found that #3 is painfully true. The not good enoughs hit me all the time and hold me back. The thing about needing people, though, is what do you do when you know you need them…but can’t find them? Or don’t know how?

  • Joseph Lalonde
    Posted at 05:02h, 19 September Reply

    That it’s tougher than I ever thought it would be

  • Danny Kofke
    Posted at 07:22h, 19 September Reply

    When my family moved from Florida to Georgia eight years ago, I had to attend a new teacher hire orientation. Even though I had taught for six years before we moved, I was a new hire in the state of Georgia and had to learn about the various things they offered such as insurance and investment options. While listening to two of the presenters that day, I thought “This is what I want to do and is my dream job.” This was before any of my books were published so I did not know how I could impress and express my interest to them. I just wrote down both of their names and contact information. A little over one year later, my first book – “How To Survive (and perhaps thrive) On A Teacher’s Salary” – was released. Here was my in! I emailed both of them, they both got right back to me and that began my relationship with two of the most impactful people in my life.

    They liked my story and we began doing some presentations (road shows) together. We drove to various school districts across numerous states to give FREE presentations to help school employees get the most out of their lives. There were times I would take a day off from teaching, drive 5 hours to Florida, present that evening, drive back home, get 3 hours of sleep and then teach the next day. Even though I did not earn a dime from this I absolutely LOVED every minute of it.

    In 2011, my second book – “A Simple Book Of Financial Wisdom: Teach Yourself (and your kids) How To Live Wealthy With Little Money” – was released. At this point I met with both of these gentlemen about working for them but there just wasn’t the right fit with either of their companies.

    Last spring, I received information from someone that basically showed me that I should start exploring the possibility of leaving the teaching profession. Not going to get into great detail but this conversation was an eye-opener. I then prayed for HIM to change my heart or change my location. Towards the end of June, I was teaching summer school. I got home and had two messages on my machine from one of the guys that I heard present 8 years ago asking me to call him asap. I did and it turned out his company was growing and they were ready to add a position that he thought I might be interested in. I interviewed in July and they asked me back for a second interview on August 4th. After this second interview I was offered my dream job with Invest-N-U as a retirement consultant and now get to help teachers learn how to manage money better and invest for their futures.

    After getting hired, I thought back to all that has transpired since I first saw David (my new boss) present. I have now written three books, appeared on over 50 television shows, been interviewed on over 450 radio shows and driven/flown thousands of miles to present. There were times when I was presenting to a room of only 10 people or talking on a radio show in which maybe one person was tuning in but I kept hustling until that door finally opened.

    I am just completing my third week working with Invest-N-U and have already learned so much. Number one is no job is perfect. I do LOVE my new gig and feel as if HE put me here but there are some drawbacks. I now have a one hour commute to get here (compared to a 5-minute drive when I was teaching). I also see less of my family. I was fortunate enough to teach at the same school where my wife and also where both of my daughters attend so we had a lot of family time. I am not looking back and know I am exactly where HE wants me to be but am just pointing out that chasing a dream can actually be more difficult than following the norm but it is so worth it!

  • Derek
    Posted at 07:46h, 19 September Reply

    I just launched my own business online. I was the marketing manager for a Christian bookstore many years and today I write and develop courses helping pastors and churches leverage social media.

    What I learned is that things take longer than anticipated. I always underestimate the amount of time it’ll take to get a project done, write a post, develop a product or course and so on.

    I’ve also learned not only does the buck stop with me, it also starts with me. Procrastination can be a killer.

    On the upswing, that feeling I get knowing that I’m impacting lives and even whole church communities because I’ve taken a risk of starting this online venture is amazing!

  • Jesse Phillips
    Posted at 11:17h, 19 September Reply

    The No Boss thing is so true! I’m a terrible boss! It’s so hard to keep myself on task! So ironic. We really do all need each other, we all bring something valuable to the table. Both working by yourself and with a team have benefits and challenges.

    I appreciate your honesty and transparency and telling it like it is, Jon. Thank you!

  • Ted Sperides
    Posted at 12:41h, 19 September Reply

    The thing I have learned in my first year and a half going after my dream is that success happens in it’s own way and it is different for everyone. Someone may say, do these 5 things and you will be successful, another person may say do these 5 other and completely opposite 5 things for success. The truth is, every business, every person, and every industry is different and the only way to “win” is by showing up when it gets hard, truly caring about what you do and delivering results/value you to your customers. Also, those first few people who “bought” from you when you were first starting out, and decided to take a chance on you/your business. Treat them like royalty. Oh yeah, and the days when you are just about ready to throw in the towel, give yourself one more chance, and there is a magic thing that happens usually… it somehow works out.

    I could go on for days…


  • AC
    Posted at 13:10h, 19 September Reply

    Thanks for that,

  • Heather
    Posted at 13:54h, 19 September Reply

    This past year has been my year to take the leap and start chasing my dream full time. What I wasn’t ready for was the immense amount of fear and doubt that can creep up at a moment’s notice. One moment you are flying high because of a success and then POOF, you feel like an idiot. But when I think about where I was a year ago and where I am today, well, frankly the doubt creeps away a bit faster. As always, thanks for your words Jon.

  • George
    Posted at 14:40h, 19 September Reply

    Exactly the words I needed to hear! We (my wife and I) started a new ministry during the summer and it is like you were listening in on our prayers and conversations then decided to write this. HA! I am so happy I am not the only one that goes through this. We should start a support group. 🙂 Thanks for the wonderful post!

  • Garrhet Sampson
    Posted at 06:05h, 20 September Reply

    This post definitely describes my experience! On top of the blog I run my wife and I also are self employed as proofreaders. You’re totally right about the temptation to become a work-a-holic. I’ve found it helps to pencil in time off just as diligently as you pencil in your work time. That way you know when you’re supposed to be hustling and when it’s time to relax!

  • John R. Meese
    Posted at 09:11h, 20 September Reply

    COngrats on a full, successful year on your own, Jon. Thanks for sharing the insights you’ve taken from that! Sharing your honest experience after taking the leap of faith is encouragement for those of us not far behind 😉

    P.S. It was great to see you at the HoP book launch in Nashville last Monday. Sorry I didn’t get a chance to say hello in person!

  • Jason Vana
    Posted at 10:31h, 21 September Reply

    You already mentioned it in your post, but I’m learning that it’s okay – and beneficial – to need help. When I allow others to use their strengths to grow this dream, the dream only gets better.

  • Micki Vandeloo,GPC
    Posted at 16:20h, 21 September Reply

    I have also been growing my coaching and writing business over the past year, and have found that “being my own boss” has been exhilarating, stressful, frustrating and the most fun I have ever have. I also have found that, once you open yourself up to receiving your own great ideas, they start to flow. Finally, I have discovered that I need to pace myself. I do still have a “day” job, and, if I am not careful, I will work 12-14 hour days for days on end.

    I have grown so much in the past year, and can’t wait to see what the next year brings! Thanks for sharing what you learned, Jon!

  • Anthony
    Posted at 22:21h, 24 September Reply

    I’ve been living my dream for nearly 7 years, 4.5 of them full-time. It’s taken me a lot longer to learn some of these things than Jon 🙂

    The only one I’ll add is this:

    Chasing public affirmation is feeding a monster. It can’t sustain you, won’t fulfill you. If you love what you do, do the best work you can possibly do. If that brings affirmation from people, great. But your happiness with your work cannot depend on how it is received. You have no control over that. The only thing you can control is the work itself. Do work you’re proud of, then do it again, and again.

  • Eugenio Cebollero
    Posted at 00:23h, 08 October Reply

    To point #6 in this blog post’s list, I’m unsure of what dream it is you are chasing which makes me a candidate for point #4. Having been a follower of yours since “Quitter” and “Start” I presumed the impetus and inspiration behind those books were shaped around becoming the best version of oneself in order to prosper in a career, employed or self-employed, which complimented the vision, mission, and underpinnings of your previous employer. I understand that you are an excellent orator, wordsmith, and master of wit and working those talents into print is something I would be pursuing as well if those talents suited me. Reading the “About Jon” bio, I still cannot pinpoint your vision, or mission. (Again, I fall into category #4.) In a sense, I feel like I just discovered Forrest Gump along the run to nowhere in particular, but am simply inspired to run alongside you and see what I find out about myself along the way. And, maybe that’s just the point. Anyhow, it was a pleasure to meet you down in Brandon, FL back in Nov. of ’13 during the “Start” book launch tour. I look forward to your musings and your next body of work. Best wishes. Stay motivated. And, when you’re ready, you can stop running, but never give up the hustle. – Eugenio

  • JD Markland
    Posted at 16:06h, 20 December Reply

    This year I learned that work/life balance belongs to you. Don’t let work dictate your life and don’t look for someone else to allocate your family time. Let’s be real here – you have to deliver at work. It’s up to you to set realistic expectations and then follow through. You only have one life. You are in charge of how it’s spent.

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