I have been reading your blog for a while and have found your advice to be incredibly useful.  I recently found one of your posts from 2011 where you talk about relocating to Hermosa Beach.  That post hit very close to home for me because I’m currently going through a similar situation (although I don’t have kids).  I was hoping you might be able to offer a little quick advice.  No one else seems to understand my situation.

I’m a 35 yr old engineer and moved to the San Francisco area in May of this year.  I was laid off from my old job and luckily had an offer from a couple of guys that asked me to help them build a small search startup company.  I make about 150k per year along with equity in the company that would be worth quite a bit in several years.

I don’t mind SF, but I’m from Ohio and have Midwestern values – so San Francisco is a little different than what I’m used to – but it’s tolerable.  My original plan was to move there for 4 years, collect my equity and then leave.  However, recently my old company offered me my old position back at a salary of $108k in Ohio.  That’s a reasonable salary in Ohio, but the job in California is more enjoyable.  It feels good and exciting to help build a company from scratch.

I am very close with my mom and sister  (who both live in Ohio).  My dad passed away 2 years ago from years of medical problems, so we have a close bond due to the trauma we went through.  Needless to say it’s difficult moving away from people I love, especially my mom since she’s getting older and starting to show signs of medical problems.

I don’t want to regret using 4 years for a great career at the expense of any memories I could be making with my family.  Although, it’s difficult to pass up a career opportunity that could be worth several million dollars in a few years time.

This decision has generated a lot of anxiety.  I’ve talked to my therapist as well as others who don’t seem to have a good perspective on the situation.  I feel like you certainly understand the difficulty of this scenario.

If you have any advice or comments, this Midwestern guy in San Francisco would forever be in your debt.  Any help at all would really help me.

Thanks again for all the writing you do, as it’s really helped me in the past.

I always thought I’d have my own business by now, but life hasn’t worked that way. Specifically my wife and I had a baby and I wanted a proper job.

Now my wife wants me to start a business that will let me leave my job. She has a point, because I’m not one for sitting at a desk from  9-5. Yes, I hate it. But I would need to get a good deal of cash into that business at the beginning, and we don’t have much savings.  I have a few friends who said they could help me get investors, but I’ve seen all the trouble my friends had getting investors and I don’t know if I could do that.

 So I think I should go with a business idea that my wife and I could do together, for fun. I wouldn’t need to put money into the business. Well, we would have to have a little money, but we could use some savings. It’s just that I don’t know if I like that because the business would not let me quit my job. And my wife is pretty busy, but she likes projects.

You’ve had a lot of businesses yourself, Penelope. Do you know which business would be best for me?

Answer from Penelope:

Your goal for starting a business is to enable you to get out of going to an office from 9-5. That’s a good goal. And the smaller business idea will not meet that goal.

It seems that the only benefits to the smaller business is that you and your wife have fun. But you don’t need to invest your savings in order to have fun. And I’m sure your wife can find a project for herself without you starting a business for her.

So I think your real question is how can you gather enough funds to get the bigger business off the ground.

You are right to think that doing that is difficult, but starting a business that needs funding is often the most low-risk option on the table, and I think that may be true for you.

You have friends who understand the investment community, so it’s not outrageous to think they could guide you. And don’t underestimate the need for a guide – the startup funding community is relatively conservative with stringent rules

The game of launching a business is doing as much as you can to mitigate risk. So, for example, its risky to start a business to get out of your office job, but it’s riskier to plan to spend your life in a job you hate. Here’s a blog post about mitigating risk as you start a business

You’ll have an easier time beating out the competition if you stick to something you have expertise in. So your business should be at the intersection of the idea you like and the expertise you have. You can find practical examples of leveraging your expertise in the book The Business of Expertise, by David Baker. 

Don’t shy away from borrowing money. There’s a reason that most entrepreneurs have bad credit— you have to use anything you can get to keep your business from going under during those early, fragile months. That said,  business owners who have a plan to be profitable often qualify for fast business loans.

If this is all making you sick with stress, try a career change. Just because you hate one job doesn’t mean you’ll hate them all. I would not recommend going back to school for a graduate degree — way too large an investment for something you’re not sure of. But going to a career development site that provides you with a mentor in your field is a good way to make the career change less difficult by helping you to create a network to pave the way.  NYICD does a good job of providing that service. 

And remember that there is no way to live a life without taking some risk. When you ask people at the end of their life what they would have done differently, they almost always say they would have taken more risks. So instead of avoiding the risks of doing the business that meets your goals, try thinking in terms of intelligent risk-taking and then you’re not likely to regret the outcome, no matter what it is. 

I launched a website very recently for women starting over in mid-life. My tagline is, “Be Your Own Rescuer”. I want to create a community of support and information for women starting over at a point in their lives when they thought they would be settled. I will offer entrepreneurial opportunities, feature other women who’ve been through it, a blog, private Facebook community, etc..

When I was in that situation, I was in despair. After my divorce I thought all the good in life was behind me. But I started cleaning houses and then I realized I could grow the business by hiring people. So I quadrupled my sales and I have ten employees. Now I want to do more. I want to show women to know they don’t have to settle for the crumbs of the life they lost.

A few things I’m working on:

I am creating a course on how to start a cleaning business, with support from me through the process.

I am also creating an 8 week group coaching course for these same women. At the end of the 8 weeks, I want them to have a plan and know what next steps they will take toward creating the life they want….

My first step is putting a bunch of irons in the fire to build a mailing list, direct them to my site, by offering freebies online through Facebook ads and instagram. Possible example: Offer the overview module to the courses for free, save the meat for the paying. Create freebies my target would be interested in: controlling negative thoughts, overcoming fear and worry, 7 days of radical self-care, the number one thing I did that changed everything, how I went from homeless single mom to successful business owner with healthy, happy, grown sons, “Be Your Own Rescuer” – how I rebuilt my life in midlife, etc….

I could also join online groups catering to my target market, get face-to-face with divorce recovery groups, addiction recovery (addiction and single mom can go hand in hand at times…), single moms groups. Write blog posts relevant to my target, share them online..

My question for you is: Do you sense that I am on track with all of this? Is there anything that jumps out at you that I’m veering off-track with?