Contest update: this contest is now closed, but I will have some availability to work with motivated people in a couple of weeks. If you’re interested in working with me, check out my services page.
How are you progressing towards your own lifestyle design? What obstacles have you run into on your path to becoming self employed or location independent or whatever other goals you have? Could you use a little help or personalized advice?
I want to help, and I’m giving away 5 free one-on-one strategy sessions to readers of Free Pursuits.
Most of the major breakthroughs I’ve made in my career (especially in my new life as a blogger and entrepreneur) have come about as a result of conversations with peers, colleagues, advisors, consultants or friends. Sometimes all it takes is an hour talking through problems with someone I trust to really push past whatever I’m currently hung up on.
Those telephone or in-person conversations are especially valuable in a world where we often only interact in short bursts over social media.
I spent the first six years of my career after college consulting with Fortune 500 companies about technology, product development, project leadership and communications. It was an amazing learning experience, but I never found my true passion in that role.
Since starting this blog, I’ve discovered that I really enjoy working with individuals who are trying to live a richer, more unconventional life and to follow their passions.
I’m about to take that a step further by coaching people on how to get paid to do things they want to do, and how to design and live a dream lifestyle. I’m also offering to help develop blogs and build small businesses (find out more about all of my new services).
What’s Your Unique Situation?
Lifestyle design is a broad topic. There are countless different ways to define your own ideal lifestyle. Everyone is different. I try to write about subjects that everyone can benefit from, but I know it’s not always possible.
People are at different stages of lifestyle design, some complete beginners, some are starting to make plans, and some have launched businesses but maybe need help making those businesses grow.
There are also so many different types of careers that could support your goals. Maybe you want to run an online business or blog, or maybe you want to negotiate a remote work agreement. You might want to start a small consulting or freelance business, or just be a location independent sales person.
My point is that everyone is different on a number of dimensions, and it’s hard to really find out what your individual obstacles are and help you work through them by using the blog and social media alone. That’s where the one-on-one strategy sessions can help.
Get on the Phone with Me for 60 Minutes for FREE
Over the next few weeks, I’ll be giving away 5 free telephone strategy sessions. I’ll send you a series of questions before the call and do some research on your current blog or business (if you have one). Then we’ll get on the phone for 60 minutes to come up with a plan for moving closer to your career and lifestyle goals.
I’m giving these strategy sessions away completely free. You don’t have to sign up for anything or pay a dime.
I’m doing this to celebrate the launch of services here at Free Pursuits, and to give back to the community that has treated me so well over the past six months.
To win a free session, you only need to do two things:
- Leave a comment on this post answering the following question: What is the biggest obstacle standing between you and your ideal lifestyle?
- Click the little “retweet” button on this post and share it with your Twitter followers (if you don’t have a Twitter account, note that in your comment).
I’ll contact you by email, and we’ll schedule a time to chat. It’s as simple as that. You’ll be on the road to reaching your lifestyle goals in no time.
This contest will be open until the end of Wednesday, October 21.
What is the biggest obstacle standing between you and your ideal lifestyle?
photo by Thomas Hawk
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39 comments add your own
Hi Corbett,
Awesome! My biggest challenge without a doubt is building a business of my own that can sustain me and my lifestyle.
I think for me, money is a major factor. I’ve been trying to design my life for about 6 months. I only work a part-time job to get enough money to survive. The rest of my time, I spend on my lifestyle design blog, reading and learning, networking, etc. However, to date I feel I still can’t do many of the things I want until get more money while doing something that I enjoy doing. I love blogging. I want to earn money through it too. However, even though I am putting my heart into it, I’m getting negligible income from it.
The major obstacle for me is having the courage to start counting down to travel. I keep researching, reading, talking, dreaming, and thinking but I really just need to put a plan in motion. I have $10,000 in student loans left and am able to pay down by $1,000 each month, that is my only debt and I have savings cushion, so that part is ok. I’ve always lived a comfortable lifestyle (simple though as I grew up on a farm) because I have a job that I actually somewhat enjoy and it pays well. I do not have a twitter account.
At the moment taking things to the next level would be the biggest hurdle I’m facing, because there are so many directions Exile Lifestyle could go. Do I keep building and building and building the readership? Try to take a shortcut to the book route? Pitch a show to a traditional or online network that shares my audience? Hard to say right now. My main business should be fine to sustain me monetarily for the foreseeable future, but I would love to be able to make Exile Lifestyle my main (or at least equal) source of income.
Great idea, Corbett! Can’t wait to see how well your services do (and what a generous offer to have as a kickoff)!
Corbett – awesome idea here! I’d love to enter the contest. I think my biggest obstacle is finding the right audience for my site and then generating enough traffic to get customers. I’m struggling with that now and while I have a few concrete ideas on how to get going, I’m having difficulty with implementation.
I’m sure a good conversation with you would help, thanks for doing this – Jason.
Thanks, Corbett. What an offer!
I am finding that, in this moment, my biggest challenge is a lack of clarity. I’m at the very first step of this process: trying to find my niche, my place in the game. How do I present my unique message in a way that has impact? Who is my audience? Where to find them, and how?
I always appreciate the fresh (refreshing!) perspective you offer here, and I’m grateful for the opportunity!
Alaya
Thanks Corbett. What a great offer!
My biggest hurdle is of course myself. Staying on track has always been my biggest issue. I get sidetracked for various reasons, and lose my focus and motivation. I spend far too much time reading and learning rather than doing.
I spend too much time arguing with myself instead of bouncing ideas around with others, and since I am my own worst critic, I end up burning through a lot more time than I should.
The biggest obstacle standing between me and my ideal lifestyle is having a mastermind group of people who can help me launch my business.
Hi Corbett,
My biggest obstacle is definitely me. I become overwhelmed with possibilities and confused about which path to take, then the confidence issues come in…can I really do this, have I really got this right? I have lots of ideas..but find it hard to bring them together into a tangible plan. Although, probably the biggest challenge is belief. I love to read blogs and online information as it usually inspires me and helps me move forward, but I don’t personally know anyone who is self-employed or who I am able to call on for a bit of support or to run ideas past. Some contact with a real life person who is actually practicing a lifestyle I aspire to would make all the difference in helping me move forward.
(P.S I don’t have a Twitter account)
Nice offer, Corbett. Thanks!
My biggest hurdle is determining my “next steps.” I have a lot of ideas and am off to a decent start, but I need to clarify some bigger goals and then figure out what the next logical steps are to achieving those goals.
Each time I try to sort it all out on my own, I end up coming up with more ideas that leave me less focused.
Keep up the good work here at Free Pursuits. Good luck with your new services.
I would love a free session Corbett … it couldn’t have come at a better time as I will be free of Corporate America one week from today!
My biggest problem is that I don’t know what the problem is. I know I want to be able to travel and write freely, and I *think* I should want to monetize my blog in order to help make this a reality, but I don’t think the structure of my blog is good for that. I think the content might be okay, but I think the actual format is bad for advertising. Also, how do I find advertisers? Does monetizing my blog degrade it? Where do I find the line between making money on my blog and still providing the services I hope my blog provides to readers. I think I’m just confused about where to start to reach my goal of writing for a living. Help!
Wow. What an opportunity! I’ve been trying to figure out creative lifestyle solutions since my 2nd year in college, and while I’ve learned a lot since then, there are still many miles to go. My biggest challenge at this point would probably be not being able to identify my biggest challenge… and then those that follow in succession. Somewhere in there is the “Too much information to process and make a cohesive, well sequenced action plan.” I would really appreciate the opportunity to gain insight through meeting with you!
What’s the biggesst obstacle standing between you and your ideal lifestyle?
Easy: Fear. I’ve spent years crafting a position in the work-world M-F (like it or not). Now, I need to do a radical about-face, invest in my passion, and trust that it will come true. My dream to be location-independent, and pursue work of my own accord has always been sitting there. But I’m amazed that in the past couple of years, it’s now possible. So, fear of stepping out and how to handle a new mindset/reality is the biggest obstacle. I can probably figure out other details.
Jillian
I’ve always worked for others. I had a steady corporate job for 8 years and i really enjoyed working there. Hell, they even gave us free lunch. Then i left. I felt like i was stagnating in a profession that is going through a major identity crisis… and i was still only 32.
But i’ve been looking for my epiphany ever since.
I would absolutely love to be my own boss, and i’ve got what i think is a very solid business idea in my head; one that could contribute massively towards saving this planet of ours, one that would make me so proud…
.. but where the hell do i start?????
Thanks.
Jen
(I don’t have a twitter account)
My biggest obstacle is the fear that I am not good enough at what I do to be able to work with big clients and make big money. I feel like I need to get another degree in order to be able to achieve what I want. I also find that working for a living is an obstacle. I realize it requires work to succeed but I also find that I am just working in order to make a living rather than working towards the goals that will allow me to build the life I really want. I also want to start another business that will enable me to build relatively passive income but I am not sure how to do it yet. So, I guess that’s 3 answers to the question…
Hey Man, Awesome idea and what a great way to help out others.
For me, I’d love some good old fashioned real, raw feedback on my writing and work. I know EXACTLY what I want in my life and there are no doubts that I will get there. But I’m new to technology (I could barely write an email 4 years ago, and I have just a god-awful blog) and I have so much fun stuff to learn and many of these things can be brought into my awareness by an outside observer.
I would dig bouncing ideas back and forth with someone who is also very focused and driven on their goals and dreams. Although I’m new to reading your blog, I’ve seen your “list” and have a good feel for the overall sentiment.
I think my biggest obstacle is probably focusing. I often jump into projects, not always realizing the commitment that is involved. I also have what seems like a million ideas and sometimes I’m not sure if I should pursue them or not. My dream always has been have have my own business – a public relations firm – and being a freelance writer. Although I am just now starting to make this come true, I occasionally have doubts.
My biggest obstacle is that I have a highly creative mind; however it’s quite scattered at times- -especially as I’m in the process of reinventing my company and self.
I just started tweeting, so I’m not super familiar with this channel (something else I need to learn).
My biggest hurdle right now is that I don’t have a concrete plan of where I want my life to be going. I’m only 24 years old and while I have some ideas which I am working towards (building a website, quitting my job to travel), I know I need to develop a long term plan if I want this lifestyle to be sustainable.
Basically I really just need some guidance, so a strategy session would be so helpful!
My biggest challenge in the past two months has been really keeping myself accountable to my projects, I’ve been through a lot of new transitions (in an already existing life of transition) and working through them has forced me to reevaluate and abandon somethings I valued.
What I need is a laid out strategy to keep myself on track, I’ve got a nebulous idea of what needs to be done and who I need to reach out to but a more concrete plan of action and then tactical sections on how to proceed would be really helpful.
Hey Corbett,
What a generous offer.
My biggest challenge is to stay the course. I get started with an idea, and then abandon it for another one. So you may say part of the problem may be having clarity. That used to be true, but recently I have gained clarity to a great extent. I know what I want to accomplish, what I am passionate about, but the hesitancy in taking action comes form the past experiences of not sticking to one thing.
Anyway, I would love to work with you to set a course of action toward achieving my goals and fulfilling my dreams.
Rasheed
gosh, i think i need an erudite, reasonable but violent kick in the pants
Sweet offer! This counseling session would clear so many mental roadblocks for me and make a Huge difference in my progress.
My biggest challenge is that I’m just flat out ignorant of how to move forward in my business.
My idea is currently up & working. ShirtJax.com a social commerce site for indie t-shirt designers to sell their original shirts. The site is up, but I am clueless to how to get artists to sign up & start selling with me.
Please help! I do not have a twitter account, but I will post this link on my FB profile
Corbett,
You finally convinced me! I almost posted a comment back during your “stop lurking and start posting” initiative but this opportunity seems too good to pass up.
I am a financial professional who believes that my industry should change in more ways than one. I have become very interested in lifestyle design for a couple of reasons, the most recent being the birth of my daughter.
My obstacle is time. I feel that I am moving in the right direction but I have doubt in the fact that I’ll actually be able to pull the trigger. I would love the opportunity to discuss an exit strategy from the W-2 world with someone who can truly help.
My goal is to enjoy more time with my family (currently limited by a ridiculous work schedule), travel abroad for an extended period (I am very jealous that I did not attempt this when I was Colin Wright’s age…I lurk on his page too) and ultimately create a lifestyle that is built on desire as opposed to necessity.
Thanks.
Wow, Corbett, this is an AWESOME way to celebrate launching services.
I would LOVE to provide a service similar. I’m still in the brainstorming phrase, but I would love to run a service helping other young people launch part time freelance careers. I love working with people, and this would provide an opportunity for me to do that, as well as develop my web design and marketing skills.
One of my biggest challenges is maintaing momentum when my projects enter the no-so-exciting phases.
Retweeting now.
I think Alaya Morning and Beth’s challenge are somewhat similar to what I’m facing. We are at the the stage where we want to take off but still needs to know more how to do so .
Chris, I think you should interview 5 people who are at different stages of Lifestyle Design. Maybe it can be from a complete beginner to someone who’s already established.
Then maybe you can document the whole session and share it to other readers. So if I’m a beginner I can read the session for beginners and so on. Hey, it can be a good idea, what do you think?
the biggest challenge to accomplishing freedom of lifestyle away from the “grind” is simply – money. I have NO debt, but I have a growing family that requires groceries, a house, clothing, dental visits, and the like; all of these cost… I require about $3,000 USD to make it. But, we have considered going overseas to make our money stretch further. Any suggestions to an online biz, overseas employment, etc… would be welcomed…
No twitter, sorry chap!
Hi Corbett,
What a great incentive and unlike anyone else I’d rather not take an hour of your time since I already get it unlimited via this site. You see, I know my obstacles are time, research and ability but I already have your help, and the help of the rest of my network.
Thanks a million for the support you’ve already given and will (hopefully) continue to provide!
Caron.
My biggest obstacle(s) at the moment is money and debt. I recently was fortunate enough to land a low-paying full-time job which is barely enough to get me off of government support. Still, I’ve had a rough few years financially. Before that, I was really happy that I’d paid off all my debts and was living within my means. I’d like to be able to pick up and go and I’d like my boyfriend to come along.
From reading the posts above, it seems like I share a lot of similiar obstacles/opportunities with most of you. How to stick to one idea and one plan? When you constanly see business opportunities and you are overflowing with new, exciting ideas!
I would love to have a free session with you Corbett. I am working against the above obstacle-turned-opportunity, by selecting three main ideas where I believe I have the knowledge, passion and the market potential for these being a success! The only thing I miss, is the GREAT value of having someone to bounce off ideas with and pushing these forward, hopefully quickly – my aim is to have at least one up and running by 1st of January 2010!
All the very best to all of you,
Johanna
My biggest challenge is knowing what idea to take action on. And more directly is bridging the gap between my authentic self and putting up sites to make money. I have not put the two selfs together yet and these prevents me from doing anything. The “do what you love” message and “lets make some money” action are conflicting with me right now. Melding these would be a desired outcome of our call.
My biggest obstacle is a lack of a mentor. I have several very good ideas which need to be grounded in good practice and planning to bring them to fruition. I need someone to dialog with and help me in beginning the process of starting the businesses.
My biggest obstacle is executing. Tons of ideas, not enough consistent action on one idea.
Hello Corbett,
Like so many have already commented, my thoughts and perceptions get in the way of designing the life I want to pursuit. I am the process of “unlearning” all of the can’ts and shouldn’ts that have dominated my thoughts since I was a small child. I need helping being held accountable for both my goals and the actions I take.
Thank you for all the positive energy. A movement is brewing….
Hi Corbett !
I love your site! You and the community you are creating is an inspiration!
My biggest challenge is finding my “IT” – that is, what is my idea! I have the passion, the drive, the motivation, the vision, and the discipline but missing focus. I have several ideas and am in transition from the corporate world into my own business. I need help to focus on an area that will be my own business and allow me to design my lifestyle and be location independent. (I do not have a Twitter account.)
Corbett,
Great idea, awesome services. I’m really enjoying following you progress from taking 6 months off to being a strong voice, coach and entrepreneur in the lifestyle design realm. I’m not really putting my hat in the ring for a strategy session as I’ve engaged in enough of them over the years past. Success is a matter of trial and error…most people just don’t trial…I hope you push 5 lucky individuals to always follow their ideas and try them out. Our ideas are like a box of damp matches….one will catch flame if we go through the whole box.
Best of luck with the new service offerings and thanks for the free consult!
My biggest challenge is that my current family direction seems to contradict my vision of a nomadic lifestyle. While my wife and I were never truly “white picket fence” people, we have cherished the last 18 months of raising our daughter around a great group of friends. We love having a nice home and inviting guests over to share it with us. We enjoy growing a garden and having pets and everything else that comes with a home base.
It’s difficult to picture all this alongside a vision of traveling the world with family in tow, working in coffee shops to support us. While that sense of adventure thrills us, we know we would miss our home and everything (and everyone) that comes along with it. So many nomads talk about how they ditched their mortgage and possessions and took to the road. While that is definitely the easiest way to go, I’m not sure we could do it. So, not being able to afford both a mortgage and travel, we opt for a house and frequent 1-2 week trips.
I’d love for someone with an outside point of view to ask me the hard questions about what I truly want in life. Or maybe if I want both, can it be done?
Hi Corbett,
My biggest challenge right now is confidence 1) that I know enough to get started on my business plans and 2) that even if I fail this time around I can pick myself back up and start fresh. I’ve got the outline of a report/small ebook I want to write, but I’ve got some kind of mental block on starting the actual writing.
The other thing that occurs to me now is my desire to remain somewhat quietly in the background, while still being successful online. I have no desire to be a major player in online marketing with hundreds of thousands of people on my email list. The downsides of that life are too large for me to want it. So I think I’m pulling myself in several directions at once – I want to be successful and I want to be somewhat anonymous.
Hello Corbett!
First, awesome site! I just found it today, so I’m totally stoked to get more ideas from you. As of a few hours ago, I honestly didn’t know how to put a name to what I had been thinking. I tend to be a pretty big picture kind of guy, and I find difficulty in sorting everything out and focusing on one thing. That being said, my absolute *biggest* challenge is focusing. It’s no secret that I have a lot of interests, and I take pride in the fact that no two jobs I’ve had could be related… not even remotely. I have difficulty knowing how much is too much, and I fear that because I cannot give an elevator speech to friends/family, it sounds a bit… crazy.
I’m in the DC area, so I’m fortunate to have a rather large network of people to bounce ideas off of, but I don’t think any of them have ever mentioned “lifestyle design.” I’m intrigued by the possibilities and would definitely like to learn more!
Thanks again for offering this… it’s totally stellar!
In service,
Stephen