What’s your biggest challenge?

This blog began with a question: what is your biggest self employment challenge? We got some great answers, which you’ll find in the comments.

(I know, it says comments are closed. That’s what I get for mucking about in WordPress beyond my skill level. But comments are open, honest, and you can read previous comments here.

And if you’d like to answer the question yourself, we want to hear what you have to say. Click here to share your biggest self employment challenge.

Share and Enjoy:

{ 37 comments }

Alexia May 25, 2009 at 3:57 pm

Hiyya,
My biggest challenge being self-employed is how to be consistent with my work, admin, etc. I usually make it all up as I go along and it’s really not helping me.

Nishkala Jenney May 27, 2009 at 5:34 am

Time management, focus, and follow- through are a few things that challenge me. I find it so easy to be distracted at home – and on computer..

Fear also of targeting a market, and question if this will work in in a small city of $30,000. (College town – Ithaca, NY)

admin May 27, 2009 at 8:06 am: Hey Jenney, As you can see, you aren’t the only one with time management and follow-through issues. These will definitely be addressed in a session. And I understand fear of targeting a market. This is one of the most misunderstood aspects of growing a business, and we will talk about it for sure.

admin May 27, 2009 at 8:04 am

Thanks, Alexia. You are not alone. There will definitely be a session on managing priorities, focus, and building momentum by developing consistent (but not restrictive) work habits.

Chris May 27, 2009 at 1:06 pm

if you are planning to be self-employed, and putting your ducks in a row so to speak, what are the top 5 things you can do to prepare? (and ease the transition?)

admin May 27, 2009 at 1:15 pm: Good question! Thanks for posting it.

Barbara May 27, 2009 at 8:09 pm

I’m much more interested in delivering a great project than doing the sales for the next project.
When in the middle of a long project, there’s no time to sell the next job.
What are the best ways to keep projects in the pipeline while completing existing projects?

Molly May 31, 2009 at 4:15 pm: This is a perennial concern of Accidental Entrepreneurs, Barbara, and a great topic to address.

One thing to consider (and I don’t mean this–or my reply to Marie–to substitute for addressing the topic in the telesummit) is how you are managing time and commitments. A lot of us go overboard giving every spare hour to the current project, partly out of passion for the work and, sometimes, because we believe it will impress the client. But there’s an important difference between the time that elapses between starting and finishing a project and the number of hours required.

What would it be like to allow 3-4 hours per day for non-project work? That would include professional reading, administering your biz, marketing, networking, and developing new products and services.

Marie Kazalia May 30, 2009 at 11:33 am

I’d like to discuss some basic benefits of becoming an LLC
with someone who has done it (rather than an attorney).
I am wondering if my property tax on my residence be affected and will I have a different tax status? Or is that too specific and are you going to tell me to talk to a lawyer (who wants to set it all up for 5 thousand dollars)? When what I need to find out in advnace if an LLC will /how will it be beneficial. Can I trust those online websites who do it for a few hundred dollars?

Molly May 31, 2009 at 4:10 pm: Great question, Marie. This is the kind of thing that the Self Employment Telesummit Forums will be perfect for. You’ll be able to discuss this with other self-employed people who have formed LLCs and/or those who have decided not to. As an aside, I found my accountant to be very helpful when I was deciding whether or not to incorporate. He had no vested interest in it either way and was able to clearly explain the tax consequences. Do you have an accountant you can consult?

jamie May 31, 2009 at 6:19 pm

I feel that I am being forced into becoming self employed and I have no idea what to do – will this summit address that or is it mostly for people who already are self employed thanks

Molly May 31, 2009 at 6:26 pm: Jamie, that’s the million dollar question.

This telesummit is for newly self-employed and about-to-be self-employed people. Lots of people who have been working for themselves for a while have signed up, but you, my friend, are the person we are creating this for.

Thanks for asking,

Molly

Suzanne June 1, 2009 at 9:38 am

Blogging and social media: I hear a lot about this being the new marketing medium, but I wouldn’t know what to say, I couldn’t think of enough things to keep a blog going. There are very few blogs I like enough to follow, and none of them are by visual artists. Might there be time to address this in the telesummit?

Robyn June 1, 2009 at 9:50 am

I have a full-time job that pays well, but I want to go out on my own freelancing. For the last year, I’ve studied and planned and done a lot of “prep” work (even joined the Chamber of Commerce and done some networking). However, I just haven’t been able to get over the fear of actually taking on a client.

I spend a lot of time on my “day job.” I’m concerned it will interfere with client commitments, and vice versa. Then there’s all the usual “OMG what if…” stuff. I just can’t seem to pull the trigger and commit.

I think if I just get one or two small jobs, I’ll get on a roll, but it’s hard to make that leap. I’d love it if you could talk about changing your mindset and getting over that first hurdle, especially when you already have a job.

Molly June 1, 2009 at 9:58 am

Suzanne, You bet there will be time to address social media. And I totally get where you are coming from. I’ve been dabbling in this area for 5 years and I’m just beginning to get the hang of it.

I’ve been talking with a terrific social media person, one who not only can explain it, but can show you how to get started without spending 8 hours a day at it. I can’t say who it is until she confirms that she is available. Cross your fingers!

Robyn, I do believe we will have the hands-down best person to address your concern. The shift in mindset from working for others to working for yourself is a Big Deal. Deciding to take on that first client is a Big Part of the Big Deal.

Thank you both for your suggestions, and stay tuned for additional announcements about presenters.

Marge June 1, 2009 at 10:04 am

Hi Molly!

I have two suggestions for the telesummit. One is help in prioritizing all the big and little and diverse things that need to get done, and how to keep focus on the longterm projects in the midst of all the immediate little demands. Second, you mentioned your mastermind team. It would be helpful to me to learn how to put together and sustain a group of people who would enjoy supporting me in my business and would help fill in the gaps between the things I do easily and well.

Thanks, I’m looking forward to the summit and a summer of related good stuff!

Marge

Molly June 1, 2009 at 11:17 am: Marge! Long time, no see.

Yes, yes, yes to prioritizing and focus. Yes, yes, yes to how to form a mastermind team.

And if I can’t get everything into the The Self Employment Telesummit itelf, be assured the suggestions you all are making will show up in pre- or -post-telesummit resources.

Ann Deaton June 1, 2009 at 11:31 am

I’m more than five years into self-employment now, and love all that it offers in terms of flexibility, challenging work, and income. Two things I’d like to know more about at this stage of my development are (1) the best ways to leverage your presentations and writing to make them more available and to generate additional income; and (2) when it makes sense to have an office outside of your home and the other options that exist (e.g., shared office space) when you do need a separate office. Thank you!

Molly June 1, 2009 at 12:06 pm: How fun is this? I keep running into people I have talked to in ages.

Hello, Ann! It’s great that you are doing so well (and I am not surprised). Your first question (about leveraging presentations an writing) is pretty advanced for this telesummit, which is designed for the newbie or the person who has been self-employed but never really made a go of it. However, that doesn’t mean I can’t help. My next project (tentatively scheduled for Janaury – March) is called The Three Legged Stool. It’s all about how to integrate three income pathways that offer mutual leverage.

The idea is that one-to-one services (coaching, consulting, massage, portraiture, whatever, aka the first leg) generate learning that is of value both to your clients and your colleagues (what some might call your competition). This learning turns into articles and presentations, which you can leverage to market your work and also as income producing information products (second leg). The third leg is training, which emerges out of and feeds into the other legs. This can include seminars, workshops, speaking, teleclasses, etc.

These three legs are available regardless of whether you are a coach or a florist. And I am excited down to my toenails about developing the course. So please, stay tuned!

As to the matter of office options, that sounds like a great question to address in a pre-conference event. And I know just the person to invite. I’ll tell the world when he says, “yes.”

Cheers,

Molly

Fiona Purdy June 1, 2009 at 4:36 pm

Being positive and not giving up when trying to keep going with my business especially when I need to invest yet more money into it, but no money is coming in from the sale of my artwork to fund it. A real catch-22! Arggggggggg.

Thank you for all of your free advice Molly – BLESS YOU!

Molly June 2, 2009 at 1:52 pm: This is so important, Fiona.

I’m reading Pam Slim’s Escape from Cubicle Nation, and she talks about making conscious decisions about how much to invest in a business and what fall back plans to make when income doesn’t materialize on schedule. Her take on this is sensible, balanced, and kind. I strongly recommend her book.

And–Ta Dah!–Pam is going to be one of our presenters! I am really excited about this. Woohoo!

Rosalyn June 4, 2009 at 3:47 am

I think my biggest challenge is not allowing emotions to dictate.

Some days I’m on top of the world and feeling more than competent to meet all the challenges that self-employment throw at me. Other days there are things happening in my personal life or I have problems in my business and then everything feels impossible.

My feelings have too much of an influence on my productivity!

Rosalyn

Chris June 5, 2009 at 1:59 pm

I need to get SOMETHING going fast, because with all the rising prices we are bleeding money faster than it’s coming in. Problem is, I don’t know WHAT to do first. I really would like to get into my craft/art, but I know that will be a long-term process, and I am REALLY not interested in anything like coaching/consulting/teaching which is what most of the online businesses seem to revolve around. So, where is the best place to start when you’re starting from scratch is the main issue right now.

Molly June 23, 2009 at 5:01 pm: Chris, you wrote, “So, where is the best place to start when you’re starting from scratch is the main issue right now.”

Yup. And the starting place is exactly what Pam Slim will be addressing in her kick off session on September 15. Dick Carlson’s session on content-preneuring will also be useful. Dick is a lifelong student of how people learn. He’s fed up with the shallow learning experiences that are being passed off as valuable content by so many internet marketers.

What does that have to do with you?

Well, it’s been said that there’s a book in everyone. What that means to me is that each of us has knowledge and perspectives that can be valuable to someone else. Dick will be showing us how to choose ways to formulate and package that knowledge so that it actually delivers value to other people. This applies whether you throw pots or pizza dough for a living.

Stay tuned!

Laurie Sonnenfeld June 9, 2009 at 1:04 pm

My biggest challenge is how to redesign my company. I want to develop a vision that supports the following: I want to design a structure that will encourage people who are a good fit to become a part of my company. People who care about using sustainable practices and have green and progressive values. People who care about increasing the sense of community and “village” in our city. I want the new design to foster creativity and collaboration, and I want to have accountability built in and be able to lead while empowering others. I want people to have good people skills and good boundaries and be fairly self aware. I want it to feel safe for people to bring their heart to the work they do and for them to be inspired to work both “on” and “in” the company, and I want it to feel safe for me to lead and be the owner, even if I take on partners. I want others in the company to have a stake in its growth and well being. I want a lively, fun, inspiring work environment. I want others to help carry the momentum. I want to be able to step away from time to time and have enough good people and systems in place that it can run itself for a little while. I want it to grow gradually and sustainably and I want to enjoy participating and observing as it develops a life of its own. Thanks for giving me a form to get this burning question out!

Molly June 23, 2009 at 4:57 pm: Hi Laurie, What a great vision!

I would have sworn I wad responded to it, but either I was dreaming or my response got eaten during our recent change in Web hosts.

One question that occurs to me as I re-read what you posted: What structures will encourage in you the qualities you want to encourage in others? I’m not saying your company should treat others the same way it treats you. You are the owner. But I am saying that when you have good boundaries and are clear about your standards and expectations of employees, and when you are clear that your standards and boundaries serve everyone, you will be able to see what works and what doesn’t.

In my experience, the structures you are talking about are rarely, if ever, known in advance. What can be known is what you want the structures to do and how you will evaluate the results of your experiments.

Connie S Owens June 10, 2009 at 1:35 pm

My greatest challenge is to stay focused and stop thinking about the lack. Chasing after the next great idea to help me is a distraction. How to know which tips and ideas to take the time to read and which ones to ignore. I read as many as I can and the day is over. Keep the faith and focus, not always easy. Thank you.

Molly June 23, 2009 at 4:53 pm: You said it, Connie. “Keep the faith and focus, not always easy.”

As I wrote in response to Mgta, “I hear you about spending too much time collecting advice and too little time putting it into practice.”

We’ll be working hard to make the telesummit both inspiring and practical.

Ellen June 10, 2009 at 10:33 pm

Where do I even begin?
There are many excellent points already made.
I would say that a large challenge that self-employed people face is that we are all but invisible in the eyes of policy makers and “Big Business.” That means that policy is made and carried out that not only ignores our needs, but sometimes has harmful consequences.
It also means that such things as obtaining affordable health insurance is a struggle since we are, for the most part, herded into individual plans where we endure the scrutiny of tougher underwriting and little ability to negotiate terms and conditions.
It also means that when the economic downturn hit big-time, AIG and Citibank were bailed out with our taxpayer TARP money, W-2 employees had eligibility for a longer term of Unemployment insurance, but the self-employed individual who saw sales fall off a cliff was on her own.
Self-employed people are not organized politically, so we are neither seen nor heard.

Molly June 23, 2009 at 4:50 pm: Ellen, I’m glad you raised the question of health insurance. One of the benefits of networking with other self-employed people is learning about sources of affordable health care in our own area. This is one of the important conversations that can happen in The Self Employment Telesummit forums (in the member area). And one of the keys to organizing politically is to equip ourselves with basic business skills. After all, getting ourselves known and getting the attention of policy makers requires the same skill set: outreach, relationship building, educating, and demonstrating benefits.

I hope you will raise some of these issues in the forums, which are going live this week.

Roxanne June 15, 2009 at 11:12 pm

My biggest challenge is how can to balance continuing to bring in new business when I’m working full time with a customer? I end up creating gaps when I could use the revenue because I’m committed with a customer and wanting to build my business at the same time.

Molly June 23, 2009 at 4:45 pm: Hey Roxanne,

Isn’t that the truth? It’s so easy to get caught up in serving the customer at the expense of future work. Sometimes, even at the expense of current rest and relaxation.

It’s one thing to say, “schedule time to market and develop relationships with prospective clients even when you’re busy.” It’s an entirely different thing to do it.

Sean D’Souza’s presentation on chaos will shake up some of our ideas about time management and delivering value to clients. I don’t want to spoil the surprise, but I will say that following his methods have made my life a whole lot saner this year.

Caitlin June 18, 2009 at 12:16 pm

Hi there! This summit sounds great.
I’ve made the leap, and left the corporate life to do my big thing. Nothing beats an office with a few of the garden and the cat pestering me all day.
My biggest challenge is motivation, and calming the inner voices that tell me I’m nuts, it won’t work, etc.
Thanks!

Molly June 23, 2009 at 4:43 pm: Caitlin, an office with a view of the garden is, indeed, precious!

You wrote, “My biggest challenge is motivation, and calming the inner voices that tell me I’m nuts, it won’t work, etc.”

That is so common. This is the biggest challenge I face after 20 years of self-employment. Fortunately, while the challenge remains, it gets easier to deal with.

Pam Slim, author of Escape from Cubicle Nation, has an especially good feel for this issue. She combines practical knowledge and clear instructions for moving ahead with an attitude that promotes sanity and even kindness to oneself.

The forums, which are going live this week, will provide an additional safe place to vent frustrations and fears and give and receive support. These online bulletin boards are available to everyone who registers for the telesummit. And, now that they are live, you get access as soon as you sign up.

Caitlin June 18, 2009 at 12:16 pm

(that’s supposed to be “view of the garden”)

Mgta June 21, 2009 at 1:41 pm

My biggest challenge in being self-employed is staying focused and taking action towards the goal. I spend too much time collecting advice and not enough on putting it into practice.

I also agree with almost all the other posts about starting up a small business. It has a lot of challenges.

Molly June 23, 2009 at 4:36 pm: Boy do I hear you about spending too much time collecting advice and too little time putting it into practice. That’s why The Self Employment Telesummit is designed to do three things:

1. Help self-employed people can make informed choices about where to focus their time and energy, what tasks to take on and what they can let go of.
2. Help folks decide where to invest their training and development dollars.
3. Provide a pathway for implementing these choices and measuring the results.

Number 3 can’t happen in a one-week event, but there will be follow-up options available.