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Thinking about leaving a well paying job to freelance

I have a great job that pays well, but I really want to have my own business. My plan is to freelance while I figure out what product(s) to build. My question is this, how can I make the plunge without putting my family at too much risk? Any advice for taking the plunge?

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    It's been nine years since I made the full-time jump you're thinking about taking. I was single with minimal expenses at the time but I was still nervous just like you are.

    I'm a client services guy mostly, and not a product person, so I can speak best from that angle. Here's my best "real talk" advice without knowing any concrete details about your situation:

    • If you aren't doing work on the side right now then don't quit your job until you have done so. This can be tricky depending on your employer's rules (if you feel they will or can enforce said rules). Starting part-time helps you make mistakes with a safety net and gets you started building a base. You need to hit the ground running full-time with at least a real portfolio but ideally clients with recurring work or possible future leads.

    • When/if you decide to go out on your own the first business you should contact about freelance work is your employer. This move was the smartest thing I did and my old company has been one of my best clients for nearly a decade. This obviously assumes you will have an amicable exit.

    • Pick a niche and ride it. Personally, I got started building web apps and sites for professional baseball teams. When my first project was done it was relatively easy to find the next and that snow balled for several years. The smaller the network of people in the niche the better too. Baseball people all know each other so it was easy to get introductions or just do cold emails with references attached. Please, for the love of God, don't quit your job to make brochure websites or some other commodity.

    • How do you get along with your boss? One of the common refrains from people when I tell them I freelance is that it must be nice not having a boss. I immediately tell them I have X number of bosses where X is my client list at the time. When they hear that the smiles leave their faces immediately. Be prepared to have many masters.

    • Get a good accountant and form a corporate entity. You can make an LLC, depending on your state in America, in a matter of minutes. I would avoid services like LegalZoom because of the cost, delays and the large amount of upselling. Do not eff around with taxes and paperwork and if you have doubts pay a professional to help you.

    The bottom line with new freelancing, regardless of your personal situation, is that you can't do it without risk. People will tell you to make sure you have a lot of money saved up, which is very sound advice, but if you suck at this that money will vanish quickly.

    I would start small, make sure this is something you really can and want to do, and if it goes well for a period of time think about going full-time then.

    If you want some more rambling advice hit me up on Twitter: @bjplink

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      Hey there, this is great advice. I'm interested to hear what you think of my situation. I like my current job but the pay is low. I am good at what I do (sales/client relations) so I applied to a similar full time role but the pay is roughly the same. If I get offered the 2nd job, is there a way I can work for both companies? How can I say to my current job, and the new one, I'd like to do your work but on a part-time, and somewhat remote basis. It seems like you have experience going from full-time to freelance and having your 1st client be your former employer. Any advice on how you approached it would be awesome!

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        When I quit, on a Monday morning, I went in with a plan to give two weeks notice and then suggest I fill in part-time until they found someone to take my place. They agreed right away.

        I think it was easier for me because my job was technical in nature. I was hard to replace, in the short term, and I had a modest track record of success during my time there. And we just all really liked each other so continuing the relationship seemed like a good idea.

        As for your personal situation, I don't really know what to say. I would be careful you don't ruin both situations. If your current employer thinks they can live without you they will let you walk. Then if the other job falls through you're in a tough spot.

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          I appreciate the advice. I think you're right it's probably easier to convince your current employer to let you stay on part time as they know how valued you are already and harder to replace. The newer employer is tough..I'll let you know what happens. Thanks again!

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    Is a middle ground an option at all? When I was ready to take that plunge again recently, I asked my day job if I could work part time, 3 days/week. I wasn't sure if they'd say yes, but I asked for what I wanted, and as it turned out, they said yes. It's definitely helping to ease the transition while I work on projects. I work for them Mon-Wed, and work on projects Thur-Sun.

    On another note, I've freelanced in the past, and one of the things that I underestimated then was the amount of time I'd spend hustling for new projects because I didn't have a network of potential clients at the time. What I ended up doing, was finding a couple of agencies that utilized me for their overflow work, so even though the rate was a little less, it worked out because they kept me busy and I didn't have to worry as much about hustling sales.

    Another consideration is any loans/financing needs, which may be tougher to get once you're freelancing. For example, I knew I wanted to re-fi my house, so I made sure to get that done first, before I went to part-time.

    Take your time and plan and prepare. No need to rush if you have a great, stable job. You won't regret taking the extra time, and when you do make the move you'll feel much more secure about it and less like you're just jumping blindly off a cliff.

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    One thing that I wish I had spent more time on before making the jump from 9-5 to freelance/consulting was putting together an audience of people that already know, like, and trust me (current and former colleagues, friends, family) and then spending some time figuring out how to sustainably grow that group of people.

    That list makes a big difference in terms of:

    1. Having people to validate business ideas and product/service offerings (e.g. what problems do you have / would you pay for this?)

    2. It gives you real world experience understanding the difficulties in building the people/customer side so you don't fall into the trap of focusing on the building/coding part for too long (which I'm guilty of doing... more than once)

    3. If things aren't going as planned you have a well defined way to reach out to this network to look for things to help you out, be that additional side income, a part time job, key connections/introductions or just general moral support

    Best of luck!

    Joe

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    As others have said, you need to have a good handle on your budget and how much you need to meet that.

    Assuming you know that, I would propose an alternative solution to going all in. Work part-time.

    I switched jobs about 18 months ago. I now work three days a week for a company I love and two days a week on my own projects. The three day a week job meets my money needs and gives me health insurance. Plus I really enjoy it.

    The downside of this is that my own projects take longer to finish, but the upside of infinite runway via the part time job is well worth the risk in my opinion. Hell, I would not quit even if my businesses were generating enough money to cover me.

    Give me a shout if you want to talk more offline too, happy to help!

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    Well, if you have a job that pays well, dont go freelance.

    If you have your own business, you will have to learn one special skill: to sell.

    And to make a business that it is better than a great job that pays well, you need to sell a lot! I mean it.

    GO, and spend some money on good courses about marketing and sales. Try to sell things, learn how to design a sales funnel, play with paid traffic, etc.

    After some months, you will start to understand how to offer what other people wants.

    Then, you can start to make a small team of freelancers to make prototypes. If you are a programmer, dont code! do not go on that route. Pay people to build your ideas, and you will be the project manager.

    That is my advice. I understand that you would love to spend time doing what you like, and get money for that. But it does not work on that way

  6. 1

    If you don't want to putting family at too much risk, I recommend insuring your family in General Insurance https://generalinsurance.com/ . They cover everything.

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    Hey there,

    I'm in a similar position as the one you want to be in. Im freelancing right now as a front-end web developer and I'm building my own products in between projects.

    I started without a network or referrals and now I have a few freelance projects going as a front-end web developer.

    I'm 23 and don't have a family so I took a bunch of risks that I wouldn't have if I had a family to support. Like quitting my job to jump in head first and moving to Thailand for cheaper coats of living. Still though, I hope these tips can help you.

    1. Sign up for freelance lead services like Broadway Leads or Workshop. Both are extremely helpful and send you tech leads everyday. Email someone every single day.

    2. Put together a landing page targeting who you're trying to contact. My landing page is targeted towards senior level managers in tech companies looking to bring on a front-end web developer. https://derickruiz.com/hire-me

    3. Email them with a short portfolio of stuff you did right on the email. Here's an email that worked a lot for me. https://pastebin.com/2N7FDRZi

    No one is going to look at your landing page until after they've already decided to hire you I've seen. Just as confirmation to their decision. The email is the most important.

    Also, don't be afraid to look on Twitter for people looking for freelancers. I've found some luck on there.

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    Why can't you skip freelancing and stay at your job while you figure out what to build and sell?

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    Start small and work on projects in your, cough, spare time. If reading from other founders has taught me anything, it's that the full time+spare time allocation is going to be at least as much of a time investment as you'll need running your own business. Starting this may means that you can at least see how your family reacts to this kind of schedule. Plus, after some period of time, you'll have product(s) on which to base your business model.

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    This comment was deleted 7 years ago

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      This needs to be its own blog post. Solid advice.

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      That is excellent advice, thank you.