I have been freelancing for over 15 years, but following a recent upheaval in my personal life some 6 months ago, it has felt a bit empty and unrewarding. So for 6 months I have plowed on, doing the same things as usual but without the same passion or love of it any more. So I really was primed for a big change, but not sure what I could do to change things dramatically enough.

So after a presentation I gave at a meeting at one of my long term customers today, which went down really well (I was actually being very brutal about the mistakes they had made) I was offered a job with them. And much to my own surprise I accepted their offer.

I am now worried that after so long being self employed that I am going to find it hard being part of a team again, where I am no longer independent or an outsider.

Does anyone have any suggestions or advice about how I can manage this transition? In particular how to make it a success now I have committed to it.

The team I am joining is very good. The customer that will now be my employer is growing and expanding rapidly. I know the owner quite well and I respect him a lot and have enjoyed working with him. I have done project work for him as a freelancer for over six years. I am committed to this and want to do well, but am now nervous that perhaps I am too much in the 'freelancer' mindset, am too steeped in the self employed "work when I want to" type mentality, that actually stepping back into the workforce will be more difficult than even I am expecting.

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    yeah probably not a great question... but.... eh.. I think you're worrying unnecessarily. Yes it will be an adjustment and you surely will hit those interactions where your "freelancer mindset" will be "against the norm" for other employees -- but.. that may be what causes you to excel in the position. Face it, you'll most likely be more decisive and fall naturally into a more leadership role. I think the largest issue you'll have is punching a time clock -- or at least that would be my largest hurdle. – Scott Oct 5 '16 at 21:13
  • I must admit that one factor in doubting myself was the not waking up at midday on occasion after a night out and flopping into the office when I felt like it! Perhaps I am just childishly nervous and thanks for your positive comments. Just wanted input from other freelancers that might have tried the same transition themselves perhaps. A weakness of the team is certainly leadership, and seeing the bigger picture, that is one thing, I think, the owners and directors are hoping I will add. – PaulD Oct 5 '16 at 21:32
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    Yeah giving up those occasional 2pm naps would be hard :) – Scott Oct 6 '16 at 1:55
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    That will not be easy. In our company the CEO is very stringent about hiring ex-freelancers on payroll because according to him it can only result in trouble. In the end though, I think it's about mind set. If you are really fed up with being a freelancer I can't imagine any real trouble arising. I would really miss being independent and objective as an outsider, which may not be as easy when you are an employee. – user3244085 Oct 6 '16 at 20:15
  • I don't think your CEO is too wrong as a rule of thumb. In my case I wasn't job hunting or applying for jobs, I was offered one out of the blue. Less fed up but more just a loss of passion or love for it. When I was fully booked I could not take on more work to earn more. I could never get to a point where I could afford an experienced employee, nor had the time to train an apprentice. I kinda wish I had avoided service sector and gone for a product line. Too late now. And yes, I too will miss those things, but it is not all good when the passion has gone. Thanks for the comments though. – PaulD Oct 6 '16 at 22:03

I don't know if I am going to properly answer your questions because I am a convinced work-on-your-own person :) but I am going to tell my personal experiences and impressions on that wide subject...

I have been freelancing for over than 20 years now, and during these years happened that I was offered a few times to enter a company as employee and therefore close my own business.

Even though the employee position seemed more secure and comfortable for many reasons, each time I did not accept and I opted to keep the freelance-client work relationship, and in the end I was right to keep it because the secure position with years got weak and (some of) the companies was forced to fire many employees due to world or sector crisis, but I still kept and keep working nowadays with the same companies, because they pay me per job when they need it, and I am not a big fixed cost for them no matter how the businesses goes.

Also for me is not comfortable at all to re-enter to work in team inside the companies, for many reasons:

  • First of all I'm used to work alone in my office, when I go to client's offices for a day or so I don't know how can they work with all the noise, talks and distractions. I am more productive if I can concentrate 100% on the task so I ask if I can stay in a separate small room (if possible and according to the work).
  • Second when I work there I see that I go a LOT faster and I produce more in terms of quality and quantity than the employees, so that many times I find myself to wait them (sometimes happened - not wanting it - that I put them in bad light with the boss). After 20 years or self-discipline in the work place, where you must produce good and fast results, you naturally go above the standard and that can be a problem for others and for yourself too.
  • Other many reasons...

About the age factor, it is very true that after a certain age is very difficult to find an employee position inside a company because they propend to get young people (also for taxes discounts), so if you have this chance think very well if catch it or keep going on as freelance.

I think about that too a lot, what would be like in 10-20 years from now? I am on my 40's and I am completely aware that I can't keep intense work rithms as when I was 20 or 30, also many young people are showing in the business with their freshness and enthusiasm, but I don't worry too much now because I have experice by my side and people trust me as a reliable person and for now I have no problem getting and keeping clients at me (for what are my possibilities as a single person).

If you want to keep one foot in the freelance world and worry for the future or lose passion, I can suggest you to differentiate your business and knowledges, don't just stick to one or two competences but become familiar with more things, that will be also more interesting to move in new areas. Also because a table stay stable (sorry for the rhyme) the more legs it has. If a table has 4 or more legs, when you cut one leg, it still stays up in some way, this is also how many should be your streams of earnings.

For example with time I developed many skills and I work in different areas for very different clients (BTW I always wondered if this is a good or bad thing, but that kept me always with works to do and incomes), I can be a pure programmer, a pure designer, a pure photographer, a full-stack developer, or all of these togheter, which often happens (I'm also certified in some of these areas), so I always find something to do.

But as I said before, I'm one person and I'm not 20 anymore, and sometimes I feel burnt-out of stress and tasks to do, so since some time I am trying to have a side business with my own commercial company applying my knowledges for myself this time and not for others. I keep freelancing with good clients and and tring to grow other areas of business hoping that with years going on the freelance part of incomes will be less and less and the commercial part will become the main income.

Maybe you can try to do a part time employee with this company (for example 2-3 full days a week) and see how it goes and if you find yourself comfortable or not, at the same time you can keep your good clients and work for them in the rest of the time. Then you will decide what is best for you, possibly it will be a very good decision and a very good place to work for many years to come, and I really hope so for you if that is what you wish and decide to do. All the best!

  • Up until six months ago I would have agreed with you entirely, being in a similar position myself for over 15 years. However, during the last six months I felt a sudden and overriding loss of passion and love of what I do. I was fed up explaining the same thing again and again to new customers, fed up with dealing with new customers and very fed up with late payers, nit-pickers and pandering to customers needs all the time. So I was primed for a massive change. I have committed to that change now and there is no turning back. For better or for worse. – PaulD Oct 12 '16 at 16:59
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    As for going faster, you are quite right. The inefficiency I see in the workplace is shocking. When we are self employed we work damned hard when we are working. I am guessing that as an employee the motivation to work so efficiently goes, because you get paid anyway. Even the crappy skive off do-nothings get paid! You get paid for standing about chatting, sitting in meetings, going to the toilet, making coffee - us self employed people do not. We get paid when we produce, end of story. The noise is going to be a real turn off for me too I must admit. Especially the pointless idle chit chat. – PaulD Oct 12 '16 at 17:05
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    @PaulD I understand you at 100% in everything you say about annoying customers, payments, etc, that's why I don't see myself doing that for the rest of my life and I'm trying to step into other type of business (even thought since there are people involved in the work, there will always be big and small problems). But if you came to that decision means that it's time for you to make a change and have new experiences. Best of luck! – Mario Oct 13 '16 at 7:17
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    @PaulD, about inefficiency in offices, I didn't want to be pitiless in my answer, but when I go to work in the client offices there is a bi-directional shocking effect, I am shocked how much people waste time and do their best to work less possible (not all of course), and people there are shocked when I do in 30 minutes what they do in 2 hours or more! And this is more evident the more the company is big, with small companies everyone does it's best, with large companies the work and responsabilities are all watered down and most people get salary for doing very little. – Mario Oct 13 '16 at 7:25

Being a freelancer, I have at times made suggestions which some of the client's employees have made for years, the only difference being that they were largely ignored whereas I apparently convinced them virtually immediately. This made me slightly uneasy, as I feared a backlash from the employees for so easily getting 'my way' - but they were actually just relieved that the changes were finally coming.

The employer probably knew that their setup was not optimal - and therefore valued your brutal honesty.

They also probably realize the risk of hiring a long-time freelancer, but apparently feel the risk is outweighed by the advantages:

  1. They get a view from a competent outsider who is not bogged down in internal organizational squabbles
  2. They get a commitment from you, now that you are permanently employed

Sometimes an organization needs outsiders to move on. To me, it sounds like a great opportunity for you to actually make a mark.

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    That is one of the main reasons I hear for going to work for one company, for consultants and freelancers alike: they finally want to help build something instead of coming along for a specific project and then leaving. – user3244085 Oct 7 '16 at 22:19

I think you're making a mountain out of a molehill. Yeah, it's scary to suddenly have to put pants on to go to work when you're used to being in your underwear and fuzzy slippers, but remember how much self-discipline you've acquired being successfully self-employed for 15+ years.

I, too, am a lot older than 30, and while I know far too well about the age discrimination that goes on (apparently, it's not a good idea to show more than 15 years of job experience on your resume anymore), I also know that there are companies that actually value experience. I had worked for one for 7 years, and I think out of the more than 100 employees, 10 of them were under 30. (there were people in my department on either side of 70!)

I don't know if your new employer will let you telecommute a couple days per week, but an arrangement like that might help your transition. You will find that the "team spirit" (i.e. water-cooler conversations and frequent interruptions) will reduce your productivity drastically, and working from home once in a while will be a nice break from that.

I've been a freelancer for the most part for 16 years; but most of it has been as a "contract employee" where I'm supposed to be in the office most of the time, and working for one client for months or years at a stretch (and sometimes I've been converted to full-time employee).

What I would suggest to you is to keep a liquid nest egg of at least 6 months living expenses - try to put away a year's worth if you can. That way, you'll be prepared for every contingency, including you deciding you don't like being an employee and quitting, or they deciding you're expendable and laying you off. That will give you enough breathing room to either find anther job (which is possible, but time consuming) or building your freelance business back up.

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    Having that sort of nest egg is advice I always followed even when self employed. I could survive for 6 months with 0 income. If it ever got down to just 1 month left, I knew it would be time to do something else. Fortunately it never did. It is a good idea to keep this philosophy for employment too, so it the worst ever happens, it is not the end of the world and you have breathing room to stop, consider and find alternative incomes. Thank you for that, much appreciated. – PaulD Oct 12 '16 at 17:03

I hope my answer won't be too blunt. The reasons I read for being nervous are childish. The reasons for career changes should be:

  • making more money?
  • benefits?
  • will you learn more or will you remain stagnant
  • does the change reflect how you see yourself in a few years from now?
  • Thanks. The reasons are despite slightly less money, I will be learning and developing no longer as a stand alone developer working on small business sites, but part of a great team on a massive commercial project. My worry, having made the decision and commitment to change, is that having been a freelancer for so long I might cock it up because of my self employed attitude and mindset. I was hoping for some top tips to account for this, address this or that might help me ensure a successful change. – PaulD Oct 8 '16 at 13:17

Here's something you may not have considered....


I have no clue how old you may be. "Freelancing for 10 years" would suggest roughly maybe around 30 years old, give or take.

What about when you are 50?

Few, if any companies hire employees in areas of tech development or design above the age of 40. Agism is very real when it comes to employment and even more so when you are in a rapidly changing field such as tech/web. (they'll deny it, but it is a very real consideration.)

So, while giving up a successful freelancing career at 30 may seem like a great move. What happens in 5-10 years when that company no longer needs you or you are tired of working for them?

You should not anticipate being able to simply "find a new job" at 40 or 50 the same way you can at 30. So, you would need to rebuild a freelance career from scratch... or start a different profession as you get older.

While employment always feels better because it seems far more secure and stable, the truth of the matter is that it is not always a great solution long term.

Of course, you could simply freelance part time to keep your freelance business afloat. But that may cause "burn out" faster than is desirable.

In the end, I wouldn't necessarily be concerned with how successful you are at the new position, I'd be looking 5-10 years down the road and asking if being employed now is actually going to be beneficial to me then.

Being "part of a team" is great and can be very rewarding. But I'd still hesitate to give up my own business. Rememeber, no one ever becomes rich or exceptionally successful by working for other people.

  • Over 15 years freelancing. Am a lot older than 30 :-( – PaulD Oct 8 '16 at 20:36
  • Age is definitely a factor. I am acutely aware of that. Some employers see age and experience as a benefit, most see it as a negative. i.e. old means slow, old means stuck in your ways, old means not cutting edge, old means bad health. ALL these things are wrong, and illegal to discriminate against age. But it is still a massive issue that is rarely discussed. So I agree entirely. – PaulD Oct 12 '16 at 9:26

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