My current gig is going on 5 years of mental and physical angst that I can only describe as attending bootcamp again…for nearly 5 months straight. The other 7 months? Pretty chill and I can pretty much phone it in and exceed any expectations.

That’s what I’m considering for real now. Another company has been courting me and I’m expecting an offer in the next few weeks…lots of trade offs between the 2 and truthful I’m not 100% sure leaving gig #1 is the best choice - I just … hate it.

Leaving #1 also means leaving about $20k in bonus on the table if I bail before April.

Here’s the conundrum…I’m considering taking the the offer for gig #2 and doing the work for gig#1 during off days and in the evenings. I’ve done this long enough to know that I could EASILY make it to April, collect my bonus (and the paychecks they I’ve been earning) and then bail before the part of my job begins that I actually have to show up for.

Or…I may get a few months into gig#2, realize it is the wrong fit, resign, and go head first back into the insanity of gig #1.

I know I’m not under any contract that prevents me from holding 2 jobs; and I’m very confident that I can without too much stress complete the work-from-home tasks of gig #1.

Anyone ever do this?

I am also wondering if there are any tax implications.

Tough choices for sure.
I can relate with the busy months and then slower months as my business is kind of seasonal to a point. It's steady but April through the beginning of September are killer.
Go with your gut I'd say.
Taxes of course are a different story. You'll have 2 W2's come tax season and depending on how much you make/made, you could end up owing or it might work out. Maybe look at tax tables and go from there. Of course you could have more taxes taken out to offset if need be.
Good luck.

I've never done that, and can't think of any tax implications, other than getting placed in a higher tax bracket. It sounds like a win, if you can make it to April in both positions, collect the bonus, and at that point, have the option of choosing which gig to stay with. Best of luck and be well.

To deal with the tax issue, remove some exemptions on your W-4 so they hold out more taxes or put an extra amount aside in a savings account to pay when you file. Just be sure you withhold more than you paid last year so there's no penalty for under-withholding. Not a big deal as long as you can pay when needed.

The rest of it you seem to have figured out. As long as your not violating any contract and can put in the time and effort without burning out, why not? Just read all the small print before signing anything and read anything you may have signed when you got the first job.

As a non-repentant, chronic workaholic, my questions would be:
Do I have family, and how would they be impacted?
What would I consider the “F this” point in either job to drop one for the other?
If I wanted a week (or a day) off, how would that work?

If it wouldn’t interfere with family stuff, I’d probably try it. With the absolute plan to have one job after April.

Seems like it's a good opportunity to Test Drive the new job. As for Taxes max out any retirement deductions.

I like the plan...seems solid and a rare opportunity to preview a career change.

FT ?

quote:

Originally posted by smschulz:
FT ?

Full time.

I just discussed this with my accountant.

On the first job do normal withholding.

On the second job do withholding for a single person.

The overpayment of social security should almost balance out the under-withholding of taxes.

You need to have an accountant run your number to be accurate for your income.

I was applying for a second contract W2 but did not get it.

I am still applying for second jobs.

Yes. I did work two full time jobs in my 20s to afford a car. It was pure hell and the world lost all color. During my training I worked 80 hours per week for a year. I regularly work more than 40, but I am self employed. I would never work two jobs again.
Oh the taxes. Every year that I make more money I pay more in taxes. It is not hard to calculate.
BTW working two jobs does not help anxiety and depression. Take care of yourself first.

I'm not in a position ("at the age") where I would want to work two full time jobs. But if I were younger, had lots of energy, and family weren't an issue, I think I'd be tempted to try it. Assuming job #1 wouldn't suffer, it gives you an opportunity to "test fit" job #2 at low risk. And it's only for 6 months. And if it does get overwhelming, you can quit one or the other.

As others have said, make sure there's no conflict between the two.

From a tax perspective, the government will get what they think is coming to them. Just make sure you withhold enough. As you'll have two incomes, easy to do. The only wrinkle might be social security - each employer will probably withhold until the income with them tops out, so if it's withheld over the threshold, I'm not sure about how you get that back. I'm sure it's not unheard of, so there will be a process.

If you do it, consider banking your entire second job paycheck - you're not used to having it, and you won't have time to use it anyway! And at the end of the 6 months, you'll have a good size pile of money to splurge with, pay down debt, etc.

Also, max out any retirement available, especially where there are matches.

I have done this a few times actually, as has my wife. In my profession I usually have a 90 day notice clause in my contract for quitting, so when I take a new job often have to work both/ overlap for a few months. If you can pull it off and know it is a short time thing, go ahead and do it.
If you truly hate job #1, I say quit. Life is to short going to work hating what you do. It will destroy you and lead to an early grave.

I’ve done it a few times, working in a start-up for nothing/sweat equity. It is very hard on you.

I’ve had business associates who worked multiple jobs and eventually they get caught; divided loyalties and all that.

negotiate a sign on bonus with new company. I see sign on bonuses in my line of work frequently. Maybe even schedule it to be paid In January for your tax concerns

I worked with a woman who had two full time, salaried, work from home jobs. With one HQ being in CA and the other in NY, the time zone difference made it possible to be on all the conf. calls without much conflict. But it came to a head when both companies had their annual sales conferences the same week in different cities. She couldn't be in both at the same time and it was absolutely mandatory. She had to decide which one she wanted to keep and just blew the other company event off. She was fired immediately. But she rode two salaries for a while, so she landed on her feet.

If you are young enough and have the stamina, I’d do it.

I had one full time job 40hrs, one part ti e job 20hrs, ran rental properties, worked as a consultant hrs intermittent and in weekends and attended night school.

Absolutely bonkers, it was exhilerating and could only keep the pace for two years... by then one contract job was finishing, the other tying up and things began to normalize.

4:00 to 9:am for 20 hrs a week, then up the road to full time job, which sometimes I had to leave early for night school. Weekend and so e nights as needed rental properties. I can’t get specific about my other jobs.

Frankly, after a while, It became addictive, like a combat junkie...

question is, can you handle it?

It sounds like the current gig has busy times

quote:

attending bootcamp again…for nearly 5 months straight

and not-so-busy times

quote:

The other 7 months? Pretty chill and I can pretty much phone it in and exceed any expectations

It sounds like the period between now and your bonus, when you're considering adding the second position as FT, is not in the "5 months bootcamp" period.

If you think it's feasible, there's little downside from your perspective.

I'm assuming in considering this you're sure Company 2's going to be OK with your continuing to work at Company 1 for a time. If not, I'd check that out before making the call.

A potential upside to consider - during the dual FT period, you'll have been making a reputation inside Company 2. Before you give notice to Company 1, you might let Company 2 know it's decision-time and ask whether there is anything they could do to make your decision easier (earlier salary review, straight pay hike, additional time off, etc.)

In other words, that period will probably have increased your negotiation position, since by then you'll have a proven track record in job 2.

You cannot serve two masters. Plain and simple.

I did plenty of part time jobs/side work through the years with a FT job but the idea of trying to do TWO FT jobs just seems crazy.

If you can balance both, and not deteriorate the work level at Job 1 with Job 2 why not, if there's not a contract with restrictions.

Just make sure you don't send Job 2 emails to Job 1 supervisors in error....

Tax wise, get some local tax advise, from a tax person, but withhold the max at job 2 income from both combined could move you into a new bracket, you don't want to under withhold and end up with a big tax bill...